Flights from Chicago to San Juan (ORD to SJU)

Discover more affordable routes and cheaper dates from Chicago to San Juan (ORD to SJU) within a date range.

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US$693

12:48pm - 11:36pm
Mon Mar 24th 2025

9h 48m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2238 Depart at 12:48pm from Chicago (ORD) Fly for 2h 12m Arrive at 4:00pm in New York (EWR)

Layover in New York for 3h 41m

Mon Mar 24th 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$698

1:00pm - 9:22pm
Mon Mar 24th 2025

7h 22m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:10am - 2:13pm
Thu Mar 27th 2025

8h 3m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 1830 Depart at 1:00pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 39m

Mon Mar 24th 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2022 Depart at 7:10am from San Juan (SJU) Fly for 4h 0m Arrive at 11:10am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 45m

Thu Mar 27th 2025 United Airlines · UA 725 Depart at 12:55pm from Washington, D.C. (IAD) Fly for 2h 18m Arrive at 2:13pm in Chicago (ORD)
US$715

1:00pm - 9:22pm
Mon Mar 24th 2025

7h 22m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1830 Depart at 1:00pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 39m

Mon Mar 24th 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$716

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$758

2:20pm - 11:36pm
Mon Mar 24th 2025

8h 16m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2421 Depart at 2:20pm from Chicago (ORD) Fly for 2h 12m Arrive at 5:32pm in New York (EWR)

Layover in New York for 2h 9m

Mon Mar 24th 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$758

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:07am
Fri Mar 28th 2025

9h 2m
San Juan (SJU) → Chicago (ORD)

1 Stop

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 1h 58m

Fri Mar 28th 2025 United Airlines · UA 1994 Depart at 7:20am from New York (EWR) Fly for 2h 47m Arrive at 9:07am in Chicago (ORD)
US$758

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:07am
Fri Mar 28th 2025

9h 2m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 1h 58m

Fri Mar 28th 2025 United Airlines · UA 1994 Depart at 7:20am from New York (EWR) Fly for 2h 47m Arrive at 9:07am in Chicago (ORD)
US$758

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:17am
Thu Mar 27th 2025

9h 12m
San Juan (SJU) → Chicago (ORD)

1 Stop

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 2h 8m

Thu Mar 27th 2025 United Airlines · UA 1994 Depart at 7:30am from New York (EWR) Fly for 2h 47m Arrive at 9:17am in Chicago (ORD)
US$758

6:18pm - 5:12am
Sun Mar 23rd 2025

9h 54m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2184 Depart at 6:18pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:28pm in Houston (IAH)

Layover in Houston for 2h 26m

Sun Mar 23rd 2025 United Airlines · UA 1497 Depart at 11:54pm from Houston (IAH) Fly for 4h 18m Arrive at 5:12am in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$758

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 10:46am
Thu Mar 27th 2025

10h 41m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 3h 38m

Thu Mar 27th 2025 United Airlines · UA 2290 Depart at 9:00am from New York (EWR) Fly for 2h 46m Arrive at 10:46am in Chicago (ORD)
US$760

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:17am
Thu Mar 27th 2025

9h 12m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 2h 8m

Thu Mar 27th 2025 United Airlines · UA 1994 Depart at 7:30am from New York (EWR) Fly for 2h 47m Arrive at 9:17am in Chicago (ORD)
US$760

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:43am
Thu Mar 27th 2025

9h 38m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 2h 38m

Thu Mar 27th 2025 United Airlines · UA 2100 Depart at 8:00am from New York (EWR) Fly for 2h 43m Arrive at 9:43am in Chicago (ORD)
US$760

5:15am - 3:36pm
Sun Mar 23rd 2025

9h 21m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1895 Depart at 5:15am from Chicago (ORD) Fly for 2h 58m Arrive at 8:13am in Houston (IAH)

Layover in Houston for 2h 1m

Sun Mar 23rd 2025 United Airlines · UA 1192 Depart at 10:14am from Houston (IAH) Fly for 4h 22m Arrive at 3:36pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$760

6:18pm - 5:12am
Sun Mar 23rd 2025

9h 54m
Chicago (ORD) → San Juan (SJU)

1 Stop

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2184 Depart at 6:18pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:28pm in Houston (IAH)

Layover in Houston for 2h 26m

Sun Mar 23rd 2025 United Airlines · UA 1497 Depart at 11:54pm from Houston (IAH) Fly for 4h 18m Arrive at 5:12am in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$760

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 10:46am
Thu Mar 27th 2025

10h 41m
San Juan (SJU) → Chicago (ORD)

1 Stop

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 3h 38m

Thu Mar 27th 2025 United Airlines · UA 2290 Depart at 9:00am from New York (EWR) Fly for 2h 46m Arrive at 10:46am in Chicago (ORD)
US$768

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

1:05am - 9:43am
Thu Mar 27th 2025

9h 38m
San Juan (SJU) → Chicago (ORD)

1 Stop

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2219 Depart at 1:05am from San Juan (SJU) Fly for 4h 17m Arrive at 5:22am in New York (EWR)

Layover in New York for 2h 38m

Thu Mar 27th 2025 United Airlines · UA 2100 Depart at 8:00am from New York (EWR) Fly for 2h 43m Arrive at 9:43am in Chicago (ORD)
US$783

1:00pm - 9:22pm
Mon Mar 24th 2025

7h 22m
Chicago (ORD) → San Juan (SJU)

1 Stop

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1830 Depart at 1:00pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 39m

Mon Mar 24th 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$783

12:48pm - 11:36pm
Mon Mar 24th 2025

9h 48m
Chicago (ORD) → San Juan (SJU)

1 Stop

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2238 Depart at 12:48pm from Chicago (ORD) Fly for 2h 12m Arrive at 4:00pm in New York (EWR)

Layover in New York for 3h 41m

Mon Mar 24th 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$816

2:20pm - 11:36pm
Sun Mar 23rd 2025

8h 16m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2421 Depart at 2:20pm from Chicago (ORD) Fly for 2h 12m Arrive at 5:32pm in New York (EWR)

Layover in New York for 2h 9m

Sun Mar 23rd 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$816

10:35am - 8:43pm
Mon Mar 24th 2025

9h 8m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2483 Depart at 10:35am from Chicago (ORD) Fly for 3h 3m Arrive at 1:38pm in Houston (IAH)

Layover in Houston for 1h 43m

Mon Mar 24th 2025 United Airlines · UA 701 Depart at 3:21pm from Houston (IAH) Fly for 4h 22m Arrive at 8:43pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$816

12:48pm - 11:36pm
Sun Mar 23rd 2025

9h 48m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2238 Depart at 12:48pm from Chicago (ORD) Fly for 2h 12m Arrive at 4:00pm in New York (EWR)

Layover in New York for 3h 41m

Sun Mar 23rd 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$816

6:18pm - 5:12am
Sun Mar 23rd 2025

9h 54m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2184 Depart at 6:18pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:28pm in Houston (IAH)

Layover in Houston for 2h 26m

Sun Mar 23rd 2025 United Airlines · UA 1497 Depart at 11:54pm from Houston (IAH) Fly for 4h 18m Arrive at 5:12am in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$821

1:00pm - 9:22pm
Mon Mar 24th 2025

7h 22m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1830 Depart at 1:00pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 39m

Mon Mar 24th 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$821

12:48pm - 11:36pm
Mon Mar 24th 2025

9h 48m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2238 Depart at 12:48pm from Chicago (ORD) Fly for 2h 12m Arrive at 4:00pm in New York (EWR)

Layover in New York for 3h 41m

Mon Mar 24th 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$835

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$848

2:20pm - 11:36pm
Mon Mar 24th 2025

8h 16m
Chicago (ORD) → San Juan (SJU)

1 Stop

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 2421 Depart at 2:20pm from Chicago (ORD) Fly for 2h 12m Arrive at 5:32pm in New York (EWR)

Layover in New York for 2h 9m

Mon Mar 24th 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$848

2:18pm - 11:36pm
Sat Mar 22nd 2025

8h 18m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 2421 Depart at 2:18pm from Chicago (ORD) Fly for 2h 12m Arrive at 5:30pm in New York (EWR)

Layover in New York for 2h 11m

Sat Mar 22nd 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$848

12:47pm - 11:36pm
Sat Mar 22nd 2025

9h 49m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 2238 Depart at 12:47pm from Chicago (ORD) Fly for 2h 12m Arrive at 3:59pm in New York (EWR)

Layover in New York for 3h 42m

Sat Mar 22nd 2025 United Airlines · UA 1543 Depart at 7:41pm from New York (EWR) Fly for 3h 55m Arrive at 11:36pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$856

1:02pm - 9:22pm
Sat Mar 22nd 2025

7h 20m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1830 Depart at 1:02pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:58pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 37m

Sat Mar 22nd 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$856

9:15am - 8:43pm
Sat Mar 22nd 2025

10h 28m
Chicago (ORD) → San Juan (SJU)

1 Stop

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1793 Depart at 9:15am from Chicago (ORD) Fly for 3h 3m Arrive at 12:18pm in Houston (IAH)

Layover in Houston for 3h 3m

Sat Mar 22nd 2025 United Airlines · UA 701 Depart at 3:21pm from Houston (IAH) Fly for 4h 22m Arrive at 8:43pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$858

6:18pm - 5:12am
Sun Mar 23rd 2025

9h 54m
Chicago (ORD) → San Juan (SJU)

1 Stop

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 2184 Depart at 6:18pm from Chicago (ORD) Fly for 3h 10m Arrive at 9:28pm in Houston (IAH)

Layover in Houston for 2h 26m

Sun Mar 23rd 2025 United Airlines · UA 1497 Depart at 11:54pm from Houston (IAH) Fly for 4h 18m Arrive at 5:12am in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$872

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$872

1:00pm - 9:22pm
Mon Mar 24th 2025

7h 22m
Chicago (ORD) → San Juan (SJU)

1 Stop

4:50pm - 11:29pm
Thu Mar 27th 2025

7h 39m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 1830 Depart at 1:00pm from Chicago (ORD) Fly for 1h 56m Arrive at 3:56pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 39m

Mon Mar 24th 2025 United Airlines · UA 2025 Depart at 5:35pm from Washington, D.C. (IAD) Fly for 3h 47m Arrive at 9:22pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2024 Depart at 4:50pm from San Juan (SJU) Fly for 4h 0m Arrive at 8:50pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 30m

Thu Mar 27th 2025 United Airlines · UA 1738 Depart at 10:20pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 11:29pm in Chicago (ORD)
US$880

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$880

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$885

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:10am - 2:13pm
Thu Mar 27th 2025

8h 3m
San Juan (SJU) → Chicago (ORD)

1 Stop

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2022 Depart at 7:10am from San Juan (SJU) Fly for 4h 0m Arrive at 11:10am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 45m

Thu Mar 27th 2025 United Airlines · UA 725 Depart at 12:55pm from Washington, D.C. (IAD) Fly for 2h 18m Arrive at 2:13pm in Chicago (ORD)
US$950

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$950

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$950

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$950

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$970

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1004

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1004

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1008

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1008

9:00am - 2:38pm
Sun Mar 23rd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1008

9:00am - 2:38pm
Mon Mar 24th 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1027

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Sun Mar 23rd 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Thu Mar 27th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sat Mar 29th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Sat Mar 22nd 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sun Mar 30th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:46pm - 2:27am
Sat Mar 22nd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Fri Mar 28th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Sun Mar 23rd 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Thu Mar 27th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sat Mar 29th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Thu Mar 27th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sun Mar 30th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:39am - 2:15pm
Mon Mar 24th 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sat Mar 29th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:39am - 2:15pm
Sat Mar 22nd 2025

4h 36m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Spirit Airlines · NK 261 Depart at 8:39am from Chicago (ORD) Fly for 4h 36m Arrive at 2:15pm in San Juan (SJU)

Stay in San Juan for 6 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sun Mar 30th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1057

8:46pm - 2:27am
Sat Mar 22nd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Fri Mar 28th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Thu Mar 27th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 2 nights

Thu Mar 27th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sat Mar 29th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1057

8:46pm - 2:27am
Mon Mar 24th 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sun Mar 30th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1097

9:00am - 2:38pm
Sun Mar 23rd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1097

9:00am - 2:38pm
Mon Mar 24th 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Thu Mar 27th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sat Mar 29th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

6:00am - 10:36am
Sun Mar 30th 2025

5h 36m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 Spirit Airlines · NK 264 Depart at 6:00am from San Juan (SJU) Fly for 5h 36m Arrive at 10:36am in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sat Mar 29th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Sun Mar 30th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1110

8:46pm - 2:27am
Sun Mar 23rd 2025

4h 41m
Chicago (ORD) → San Juan (SJU)

Direct

3:10pm - 7:51pm
Thu Mar 27th 2025

5h 41m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 Spirit Airlines · NK 263 Depart at 8:46pm from Chicago (ORD) Fly for 4h 41m Arrive at 2:27am in San Juan (SJU)

Stay in San Juan for 3 nights

Thu Mar 27th 2025 Spirit Airlines · NK 262 Depart at 3:10pm from San Juan (SJU) Fly for 5h 41m Arrive at 7:51pm in Chicago (ORD)
US$1118

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1136

9:00am - 2:38pm
Sun Mar 23rd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1136

9:00am - 2:38pm
Mon Mar 24th 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 3 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1136

9:00am - 2:38pm
Mon Mar 24th 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 4 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1152

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1287

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1287

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1293

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1293

9:00am - 2:38pm
Sun Mar 23rd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1355

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1355

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1364

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

2:25pm - 6:44pm
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sat Mar 29th 2025 United Airlines · UA 1045 Depart at 2:25pm from San Juan (SJU) Fly for 5h 19m Arrive at 6:44pm in Chicago (ORD)
US$1367

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

2:25pm - 6:44pm
Sat Mar 29th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 4 nights

Sat Mar 29th 2025 United Airlines · UA 1045 Depart at 2:25pm from San Juan (SJU) Fly for 5h 19m Arrive at 6:44pm in Chicago (ORD)
US$1398

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1398

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1398

2:20pm - 7:55pm
Mon Mar 24th 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:56pm - 8:12pm
Sun Mar 30th 2025

5h 16m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 United Airlines · UA 2088 Depart at 3:56pm from San Juan (SJU) Fly for 5h 16m Arrive at 8:12pm in Chicago (ORD)
US$1398

2:20pm - 7:55pm
Sun Mar 23rd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:56pm - 8:12pm
Sun Mar 30th 2025

5h 16m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 United Airlines · UA 2088 Depart at 3:56pm from San Juan (SJU) Fly for 5h 16m Arrive at 8:12pm in Chicago (ORD)
US$1398

7:20am - 12:58pm
Sat Mar 22nd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 795 Depart at 7:20am from Chicago (ORD) Fly for 4h 38m Arrive at 12:58pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1398

9:00am - 2:38pm
Sat Mar 22nd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:35am - 11:54am
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 4 nights

Thu Mar 27th 2025 United Airlines · UA 2089 Depart at 7:35am from San Juan (SJU) Fly for 5h 19m Arrive at 11:54am in Chicago (ORD)
US$1451

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Fri Mar 28th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 5 nights

Fri Mar 28th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1487

9:00am - 2:38pm
Sat Mar 22nd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

3:52pm - 8:11pm
Thu Mar 27th 2025

5h 19m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 5 nights

Thu Mar 27th 2025 United Airlines · UA 2088 Depart at 3:52pm from San Juan (SJU) Fly for 5h 19m Arrive at 8:11pm in Chicago (ORD)
US$1526

9:00am - 2:38pm
Mon Mar 24th 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Mon Mar 24th 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 5 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1526

9:00am - 2:38pm
Sun Mar 23rd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Sun Mar 23rd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 6 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1594

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 7 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1669

2:20pm - 7:55pm
Sat Mar 22nd 2025

4h 35m
Chicago (ORD) → San Juan (SJU)

Direct

3:56pm - 8:12pm
Sun Mar 30th 2025

5h 16m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 695 Depart at 2:20pm from Chicago (ORD) Fly for 4h 35m Arrive at 7:55pm in San Juan (SJU)

Stay in San Juan for 7 nights

Sun Mar 30th 2025 United Airlines · UA 2088 Depart at 3:56pm from San Juan (SJU) Fly for 5h 16m Arrive at 8:12pm in Chicago (ORD)
US$1915

7:20am - 12:58pm
Sat Mar 22nd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 795 Depart at 7:20am from Chicago (ORD) Fly for 4h 38m Arrive at 12:58pm in San Juan (SJU)

Stay in San Juan for 7 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)
US$1915

9:00am - 2:38pm
Sat Mar 22nd 2025

4h 38m
Chicago (ORD) → San Juan (SJU)

Direct

7:45am - 11:55am
Sun Mar 30th 2025

5h 10m
San Juan (SJU) → Chicago (ORD)

Direct

Sat Mar 22nd 2025 United Airlines · UA 1996 Depart at 9:00am from Chicago (ORD) Fly for 4h 38m Arrive at 2:38pm in San Juan (SJU)

Stay in San Juan for 7 nights

Sun Mar 30th 2025 United Airlines · UA 2089 Depart at 7:45am from San Juan (SJU) Fly for 5h 10m Arrive at 11:55am in Chicago (ORD)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Chicago to San Juan (ORD to SJU)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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