Flights from Jacksonville to Chicago (JAX to ORD)

Discover more affordable routes and cheaper dates from Jacksonville to Chicago (JAX to ORD) within a date range.

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US$981

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$981

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$981

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$981

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$981

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$981

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$981

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$981

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$981

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

9:20am - 2:33pm
Fri Jun 20th 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Fri Jun 20th 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

9:20am - 2:33pm
Fri Jun 20th 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Fri Jun 20th 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

9:20am - 2:33pm
Fri Jun 20th 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Fri Jun 20th 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

4:04pm - 11:14pm
Sun Jun 22nd 2025

6h 10m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1079 Depart at 4:04pm from Chicago (ORD) Fly for 2h 58m Arrive at 7:02pm in Houston (IAH)

Layover in Houston for 0h 49m

Sun Jun 22nd 2025 United Airlines · UA 2728 Depart at 7:51pm from Houston (IAH) Fly for 2h 23m Arrive at 11:14pm in Jacksonville (JAX)
US$992

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

4:04pm - 11:14pm
Sun Jun 22nd 2025

6h 10m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1079 Depart at 4:04pm from Chicago (ORD) Fly for 2h 58m Arrive at 7:02pm in Houston (IAH)

Layover in Houston for 0h 49m

Sun Jun 22nd 2025 United Airlines · UA 2728 Depart at 7:51pm from Houston (IAH) Fly for 2h 23m Arrive at 11:14pm in Jacksonville (JAX)
US$992

9:25am - 2:51pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5211 Depart at 9:25am from Jacksonville (JAX) Fly for 2h 33m Arrive at 10:58am in Houston (IAH)

Layover in Houston for 0h 57m

Fri Jun 20th 2025 United Airlines · UA 2417 Depart at 11:55am from Houston (IAH) Fly for 2h 56m Arrive at 2:51pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

9:25am - 2:51pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5211 Depart at 9:25am from Jacksonville (JAX) Fly for 2h 33m Arrive at 10:58am in Houston (IAH)

Layover in Houston for 0h 57m

Fri Jun 20th 2025 United Airlines · UA 2417 Depart at 11:55am from Houston (IAH) Fly for 2h 56m Arrive at 2:51pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

7:00am - 12:26pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Fri Jun 20th 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

7:00am - 12:26pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Fri Jun 20th 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

4:04pm - 11:14pm
Sun Jun 22nd 2025

6h 10m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1079 Depart at 4:04pm from Chicago (ORD) Fly for 2h 58m Arrive at 7:02pm in Houston (IAH)

Layover in Houston for 0h 49m

Sun Jun 22nd 2025 United Airlines · UA 2728 Depart at 7:51pm from Houston (IAH) Fly for 2h 23m Arrive at 11:14pm in Jacksonville (JAX)
US$992

9:25am - 2:51pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 5211 Depart at 9:25am from Jacksonville (JAX) Fly for 2h 33m Arrive at 10:58am in Houston (IAH)

Layover in Houston for 0h 57m

Fri Jun 20th 2025 United Airlines · UA 2417 Depart at 11:55am from Houston (IAH) Fly for 2h 56m Arrive at 2:51pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

7:00am - 12:26pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Fri Jun 20th 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:10am - 2:49pm
Sun Jun 22nd 2025

6h 39m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 563 Depart at 7:10am from Chicago (ORD) Fly for 2h 18m Arrive at 10:28am in New York (EWR)

Layover in New York for 2h 1m

Sun Jun 22nd 2025 United Airlines · UA 1658 Depart at 12:29pm from New York (EWR) Fly for 2h 20m Arrive at 2:49pm in Jacksonville (JAX)
US$992

12:55pm - 6:45pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 30m

Fri Jun 20th 2025 United Airlines · UA 2497 Depart at 5:18pm from Washington, D.C. (IAD) Fly for 2h 27m Arrive at 6:45pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:10am - 2:49pm
Sun Jun 22nd 2025

6h 39m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 563 Depart at 7:10am from Chicago (ORD) Fly for 2h 18m Arrive at 10:28am in New York (EWR)

Layover in New York for 2h 1m

Sun Jun 22nd 2025 United Airlines · UA 1658 Depart at 12:29pm from New York (EWR) Fly for 2h 20m Arrive at 2:49pm in Jacksonville (JAX)
US$992

12:55pm - 6:45pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 30m

Fri Jun 20th 2025 United Airlines · UA 2497 Depart at 5:18pm from Washington, D.C. (IAD) Fly for 2h 27m Arrive at 6:45pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

3:40pm - 9:30pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6309 Depart at 3:40pm from Jacksonville (JAX) Fly for 2h 33m Arrive at 5:13pm in Houston (IAH)

Layover in Houston for 1h 24m

Fri Jun 20th 2025 United Airlines · UA 520 Depart at 6:37pm from Houston (IAH) Fly for 2h 53m Arrive at 9:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$992

3:40pm - 9:30pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6309 Depart at 3:40pm from Jacksonville (JAX) Fly for 2h 33m Arrive at 5:13pm in Houston (IAH)

Layover in Houston for 1h 24m

Fri Jun 20th 2025 United Airlines · UA 520 Depart at 6:37pm from Houston (IAH) Fly for 2h 53m Arrive at 9:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$992

12:55pm - 6:45pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 30m

Fri Jun 20th 2025 United Airlines · UA 2497 Depart at 5:18pm from Washington, D.C. (IAD) Fly for 2h 27m Arrive at 6:45pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

3:40pm - 9:30pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 6309 Depart at 3:40pm from Jacksonville (JAX) Fly for 2h 33m Arrive at 5:13pm in Houston (IAH)

Layover in Houston for 1h 24m

Fri Jun 20th 2025 United Airlines · UA 520 Depart at 6:37pm from Houston (IAH) Fly for 2h 53m Arrive at 9:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$992

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

7:10am - 2:49pm
Sun Jun 22nd 2025

6h 39m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 563 Depart at 7:10am from Chicago (ORD) Fly for 2h 18m Arrive at 10:28am in New York (EWR)

Layover in New York for 2h 1m

Sun Jun 22nd 2025 United Airlines · UA 1658 Depart at 12:29pm from New York (EWR) Fly for 2h 20m Arrive at 2:49pm in Jacksonville (JAX)
US$994

6:30am - 12:05pm
Fri Jun 20th 2025

6h 35m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 1h 36m

Fri Jun 20th 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$994

6:30am - 12:05pm
Fri Jun 20th 2025

6h 35m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

6:20pm - 9:54pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 1h 36m

Fri Jun 20th 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1269 Depart at 6:20pm from Chicago (ORD) Fly for 2h 34m Arrive at 9:54pm in Jacksonville (JAX)
US$994

6:30am - 12:05pm
Fri Jun 20th 2025

6h 35m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:00am - 10:39am
Sun Jun 22nd 2025

2h 39m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 1321 Depart at 6:30am from Jacksonville (JAX) Fly for 2h 20m Arrive at 8:50am in New York (EWR)

Layover in New York for 1h 36m

Fri Jun 20th 2025 United Airlines · UA 1525 Depart at 10:26am from New York (EWR) Fly for 2h 39m Arrive at 12:05pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 5577 Depart at 7:00am from Chicago (ORD) Fly for 2h 39m Arrive at 10:39am in Jacksonville (JAX)
US$1002

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:10am - 2:49pm
Sun Jun 22nd 2025

6h 39m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 563 Depart at 7:10am from Chicago (ORD) Fly for 2h 18m Arrive at 10:28am in New York (EWR)

Layover in New York for 2h 1m

Sun Jun 22nd 2025 United Airlines · UA 1658 Depart at 12:29pm from New York (EWR) Fly for 2h 20m Arrive at 2:49pm in Jacksonville (JAX)
US$1002

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:10am - 2:49pm
Sun Jun 22nd 2025

6h 39m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 563 Depart at 7:10am from Chicago (ORD) Fly for 2h 18m Arrive at 10:28am in New York (EWR)

Layover in New York for 2h 1m

Sun Jun 22nd 2025 United Airlines · UA 1658 Depart at 12:29pm from New York (EWR) Fly for 2h 20m Arrive at 2:49pm in Jacksonville (JAX)
US$1097

10:27am - 4:46pm
Fri Jun 20th 2025

7h 19m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:06pm - 3:40pm
Sun Jun 22nd 2025

2h 34m
Chicago (ORD) → Jacksonville (JAX)

Direct

Fri Jun 20th 2025 United Airlines · UA 2328 Depart at 10:27am from Jacksonville (JAX) Fly for 2h 20m Arrive at 12:47pm in New York (EWR)

Layover in New York for 2h 13m

Fri Jun 20th 2025 United Airlines · UA 1144 Depart at 3:00pm from New York (EWR) Fly for 2h 46m Arrive at 4:46pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 380 Depart at 12:06pm from Chicago (ORD) Fly for 2h 34m Arrive at 3:40pm in Jacksonville (JAX)
US$1215

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

8:52am - 2:59pm
Sun Jun 22nd 2025

5h 7m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2029 Depart at 8:52am from Chicago (ORD) Fly for 2h 3m Arrive at 11:55am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 55m

Sun Jun 22nd 2025 United Airlines · UA 6366 Depart at 12:50pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 2:59pm in Jacksonville (JAX)
US$1215

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

8:52am - 2:59pm
Sun Jun 22nd 2025

5h 7m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2029 Depart at 8:52am from Chicago (ORD) Fly for 2h 3m Arrive at 11:55am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 55m

Sun Jun 22nd 2025 United Airlines · UA 6366 Depart at 12:50pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 2:59pm in Jacksonville (JAX)
US$1215

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

8:52am - 2:59pm
Sun Jun 22nd 2025

5h 7m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2029 Depart at 8:52am from Chicago (ORD) Fly for 2h 3m Arrive at 11:55am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 55m

Sun Jun 22nd 2025 United Airlines · UA 6366 Depart at 12:50pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 2:59pm in Jacksonville (JAX)
US$1215

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

1:04pm - 8:07pm
Sun Jun 22nd 2025

6h 3m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 1113 Depart at 1:04pm from Chicago (ORD) Fly for 2h 5m Arrive at 4:09pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 46m

Sun Jun 22nd 2025 United Airlines · UA 1071 Depart at 5:55pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 8:07pm in Jacksonville (JAX)
US$1215

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

1:04pm - 8:07pm
Sun Jun 22nd 2025

6h 3m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1113 Depart at 1:04pm from Chicago (ORD) Fly for 2h 5m Arrive at 4:09pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 46m

Sun Jun 22nd 2025 United Airlines · UA 1071 Depart at 5:55pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 8:07pm in Jacksonville (JAX)
US$1215

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

1:04pm - 8:07pm
Sun Jun 22nd 2025

6h 3m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1113 Depart at 1:04pm from Chicago (ORD) Fly for 2h 5m Arrive at 4:09pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 46m

Sun Jun 22nd 2025 United Airlines · UA 1071 Depart at 5:55pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 8:07pm in Jacksonville (JAX)
US$1225

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

8:52am - 2:59pm
Sun Jun 22nd 2025

5h 7m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2029 Depart at 8:52am from Chicago (ORD) Fly for 2h 3m Arrive at 11:55am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 55m

Sun Jun 22nd 2025 United Airlines · UA 6366 Depart at 12:50pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 2:59pm in Jacksonville (JAX)
US$1225

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

8:52am - 2:59pm
Sun Jun 22nd 2025

5h 7m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2029 Depart at 8:52am from Chicago (ORD) Fly for 2h 3m Arrive at 11:55am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 55m

Sun Jun 22nd 2025 United Airlines · UA 6366 Depart at 12:50pm from Washington, D.C. (IAD) Fly for 2h 9m Arrive at 2:59pm in Jacksonville (JAX)
US$1225

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

1:04pm - 8:07pm
Sun Jun 22nd 2025

6h 3m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1113 Depart at 1:04pm from Chicago (ORD) Fly for 2h 5m Arrive at 4:09pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 46m

Sun Jun 22nd 2025 United Airlines · UA 1071 Depart at 5:55pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 8:07pm in Jacksonville (JAX)
US$1225

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

1:04pm - 8:07pm
Sun Jun 22nd 2025

6h 3m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 1113 Depart at 1:04pm from Chicago (ORD) Fly for 2h 5m Arrive at 4:09pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 46m

Sun Jun 22nd 2025 United Airlines · UA 1071 Depart at 5:55pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 8:07pm in Jacksonville (JAX)
US$1525

4:40pm - 6:25pm
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:45pm - 7:56pm
Sun Jun 22nd 2025

6h 11m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 457 Depart at 4:40pm from Jacksonville (JAX) Fly for 2h 45m Arrive at 6:25pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2657 Depart at 12:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 3:40pm in Houston (IAH)

Layover in Houston for 0h 50m

Sun Jun 22nd 2025 United Airlines · UA 5524 Depart at 4:30pm from Houston (IAH) Fly for 2h 26m Arrive at 7:56pm in Jacksonville (JAX)
US$1525

8:00am - 9:45am
Fri Jun 20th 2025

2h 45m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:45pm - 7:56pm
Sun Jun 22nd 2025

6h 11m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1746 Depart at 8:00am from Jacksonville (JAX) Fly for 2h 45m Arrive at 9:45am in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2657 Depart at 12:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 3:40pm in Houston (IAH)

Layover in Houston for 0h 50m

Sun Jun 22nd 2025 United Airlines · UA 5524 Depart at 4:30pm from Houston (IAH) Fly for 2h 26m Arrive at 7:56pm in Jacksonville (JAX)
US$1525

11:20am - 1:13pm
Fri Jun 20th 2025

2h 53m
Jacksonville (JAX) → Chicago (ORD)

Direct

12:45pm - 7:56pm
Sun Jun 22nd 2025

6h 11m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5614 Depart at 11:20am from Jacksonville (JAX) Fly for 2h 53m Arrive at 1:13pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2657 Depart at 12:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 3:40pm in Houston (IAH)

Layover in Houston for 0h 50m

Sun Jun 22nd 2025 United Airlines · UA 5524 Depart at 4:30pm from Houston (IAH) Fly for 2h 26m Arrive at 7:56pm in Jacksonville (JAX)
US$1536

12:55pm - 4:48pm
Fri Jun 20th 2025

4h 53m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:45pm - 7:56pm
Sun Jun 22nd 2025

6h 11m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 0h 47m

Fri Jun 20th 2025 United Airlines · UA 1057 Depart at 3:35pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 4:48pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2657 Depart at 12:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 3:40pm in Houston (IAH)

Layover in Houston for 0h 50m

Sun Jun 22nd 2025 United Airlines · UA 5524 Depart at 4:30pm from Houston (IAH) Fly for 2h 26m Arrive at 7:56pm in Jacksonville (JAX)
US$1536

6:54pm - 11:30pm
Fri Jun 20th 2025

5h 36m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

12:45pm - 7:56pm
Sun Jun 22nd 2025

6h 11m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 27m

Fri Jun 20th 2025 United Airlines · UA 1738 Depart at 10:18pm from Washington, D.C. (IAD) Fly for 2h 12m Arrive at 11:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2657 Depart at 12:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 3:40pm in Houston (IAH)

Layover in Houston for 0h 50m

Sun Jun 22nd 2025 United Airlines · UA 5524 Depart at 4:30pm from Houston (IAH) Fly for 2h 26m Arrive at 7:56pm in Jacksonville (JAX)
US$1575

9:20am - 2:33pm
Fri Jun 20th 2025

6h 13m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1786 Depart at 9:20am from Jacksonville (JAX) Fly for 1h 53m Arrive at 11:13am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 7m

Fri Jun 20th 2025 United Airlines · UA 2331 Depart at 1:20pm from Washington, D.C. (IAD) Fly for 2h 13m Arrive at 2:33pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1575

7:00am - 12:26pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 2453 Depart at 7:00am from Jacksonville (JAX) Fly for 2h 23m Arrive at 8:23am in Houston (IAH)

Layover in Houston for 1h 7m

Fri Jun 20th 2025 United Airlines · UA 2124 Depart at 9:30am from Houston (IAH) Fly for 2h 56m Arrive at 12:26pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1575

9:25am - 2:51pm
Fri Jun 20th 2025

6h 26m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 5211 Depart at 9:25am from Jacksonville (JAX) Fly for 2h 33m Arrive at 10:58am in Houston (IAH)

Layover in Houston for 0h 57m

Fri Jun 20th 2025 United Airlines · UA 2417 Depart at 11:55am from Houston (IAH) Fly for 2h 56m Arrive at 2:51pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1575

11:41am - 5:10pm
Fri Jun 20th 2025

6h 29m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6228 Depart at 11:41am from Jacksonville (JAX) Fly for 2h 33m Arrive at 1:14pm in Houston (IAH)

Layover in Houston for 1h 0m

Fri Jun 20th 2025 United Airlines · UA 2135 Depart at 2:14pm from Houston (IAH) Fly for 2h 56m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1575

3:40pm - 9:30pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6309 Depart at 3:40pm from Jacksonville (JAX) Fly for 2h 33m Arrive at 5:13pm in Houston (IAH)

Layover in Houston for 1h 24m

Fri Jun 20th 2025 United Airlines · UA 520 Depart at 6:37pm from Houston (IAH) Fly for 2h 53m Arrive at 9:30pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1575

12:55pm - 6:45pm
Fri Jun 20th 2025

6h 50m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1938 Depart at 12:55pm from Jacksonville (JAX) Fly for 1h 53m Arrive at 2:48pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 2h 30m

Fri Jun 20th 2025 United Airlines · UA 2497 Depart at 5:18pm from Washington, D.C. (IAD) Fly for 2h 27m Arrive at 6:45pm in Chicago (ORD)

Stay in Chicago for 2 nights

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1583

6:54pm - 6:30am
Fri Jun 20th 2025

12h 36m
Jacksonville (JAX) → Chicago (ORD)

2 Stops

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 25m

Fri Jun 20th 2025 United Airlines · UA 3623 Depart at 10:16pm from Washington, D.C. (IAD) Fly for 1h 40m Arrive at 11:56pm in Detroit (DTW)

Layover in Detroit for 6h 4m

Sat Jun 21st 2025 United Airlines · UA 3442 Depart at 6:00am from Detroit (DTW) Fly for 1h 30m Arrive at 6:30am in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1628

6:54pm - 7:38am
Fri Jun 20th 2025

13h 44m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 6209 Depart at 6:54pm from Jacksonville (JAX) Fly for 1h 57m Arrive at 8:51pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 9h 36m

Sat Jun 21st 2025 United Airlines · UA 708 Depart at 6:27am from Washington, D.C. (IAD) Fly for 2h 11m Arrive at 7:38am in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)
US$1980

4:10pm - 10:41pm
Fri Jun 20th 2025

7h 31m
Jacksonville (JAX) → Chicago (ORD)

1 Stop

7:48pm - 9:25am
Sun Jun 22nd 2025

12h 37m
Chicago (ORD) → Jacksonville (JAX)

1 Stop

Fri Jun 20th 2025 United Airlines · UA 1631 Depart at 4:10pm from Jacksonville (JAX) Fly for 3h 43m Arrive at 5:53pm in Denver (DEN)

Layover in Denver for 1h 14m

Fri Jun 20th 2025 United Airlines · UA 2258 Depart at 7:07pm from Denver (DEN) Fly for 2h 34m Arrive at 10:41pm in Chicago (ORD)

Stay in Chicago for 1 night

Sun Jun 22nd 2025 United Airlines · UA 2362 Depart at 7:48pm from Chicago (ORD) Fly for 2h 24m Arrive at 11:12pm in New York (EWR)

Layover in New York for 7h 48m

Mon Jun 23rd 2025 United Airlines · UA 1938 Depart at 7:00am from New York (EWR) Fly for 2h 25m Arrive at 9:25am in Jacksonville (JAX)

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

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Roaming Sonaa

@roamingsonaa

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Andy Travels

@andy_travels

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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 Jacksonville to Chicago (JAX to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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