Flights from Boston to Chicago (BOS to ORD)

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

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US$198

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 9 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$198

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 9 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$198

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Fri May 30th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$198

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Fri May 30th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$198

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Fri May 30th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$198

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Fri May 30th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$198

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Fri May 30th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$198

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Fri May 30th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$198

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Fri May 30th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$198

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Fri May 30th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$198

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Fri May 30th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$198

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Fri May 30th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$200

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 9 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$200

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 9 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$200

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Fri May 30th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$200

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Fri May 30th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$224

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Fri May 30th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

3:18pm - 5:10pm
Sat May 24th 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1504 Depart at 3:18pm from Boston (BOS) Fly for 2h 52m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 4 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

4:47pm - 6:40pm
Sat May 24th 2025

2h 53m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 2040 Depart at 4:47pm from Boston (BOS) Fly for 2h 53m Arrive at 6:40pm in Chicago (ORD)

Stay in Chicago for 4 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

3:18pm - 5:10pm
Sat May 24th 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1504 Depart at 3:18pm from Boston (BOS) Fly for 2h 52m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

4:47pm - 6:40pm
Sat May 24th 2025

2h 53m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 2040 Depart at 4:47pm from Boston (BOS) Fly for 2h 53m Arrive at 6:40pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

7:45am - 9:42am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

6:00am - 7:57am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

12:15pm - 2:12pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1732 Depart at 12:15pm from Boston (BOS) Fly for 2h 57m Arrive at 2:12pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

6:03pm - 8:00pm
Sat May 24th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1015 Depart at 6:03pm from Boston (BOS) Fly for 2h 57m Arrive at 8:00pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$225

12:15pm - 2:12pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1732 Depart at 12:15pm from Boston (BOS) Fly for 2h 57m Arrive at 2:12pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 8 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

7:45am - 9:42am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

6:00am - 7:57am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Fri May 30th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Fri May 30th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Fri May 30th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

6:03pm - 8:00pm
Sat May 24th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1015 Depart at 6:03pm from Boston (BOS) Fly for 2h 57m Arrive at 8:00pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Fri May 30th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 10 nights

Fri May 30th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$225

3:18pm - 5:10pm
Sat May 24th 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1504 Depart at 3:18pm from Boston (BOS) Fly for 2h 52m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

3:18pm - 5:10pm
Sat May 24th 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1504 Depart at 3:18pm from Boston (BOS) Fly for 2h 52m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 4 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$225

4:47pm - 6:40pm
Sat May 24th 2025

2h 53m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 2040 Depart at 4:47pm from Boston (BOS) Fly for 2h 53m Arrive at 6:40pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

4:47pm - 6:40pm
Sat May 24th 2025

2h 53m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 2040 Depart at 4:47pm from Boston (BOS) Fly for 2h 53m Arrive at 6:40pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$225

12:15pm - 2:12pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1732 Depart at 12:15pm from Boston (BOS) Fly for 2h 57m Arrive at 2:12pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

7:45am - 9:42am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

6:00am - 7:57am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

6:03pm - 8:00pm
Sat May 24th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1015 Depart at 6:03pm from Boston (BOS) Fly for 2h 57m Arrive at 8:00pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$225

12:15pm - 2:12pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1732 Depart at 12:15pm from Boston (BOS) Fly for 2h 57m Arrive at 2:12pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$225

7:45am - 9:42am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$225

6:00am - 7:57am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$225

6:03pm - 8:00pm
Sat May 24th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1015 Depart at 6:03pm from Boston (BOS) Fly for 2h 57m Arrive at 8:00pm in Chicago (ORD)

Stay in Chicago for 3 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$229

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Thu May 29th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 6 nights

Thu May 29th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$229

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Thu May 29th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$229

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Thu May 29th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$229

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Thu May 29th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$229

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Thu May 29th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$257

9:54am - 11:51am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$257

10:45am - 12:42pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Wed May 28th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$257

10:45am - 12:42pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$257

9:54am - 11:51am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Wed May 28th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$257

10:45am - 12:42pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$257

9:54am - 11:51am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Wed May 28th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$257

10:45am - 12:42pm
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$257

9:54am - 11:51am
Wed May 21st 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Wed May 28th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Wed May 21st 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 7 nights

Wed May 28th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$258

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

9:15am - 12:50pm
Thu May 29th 2025

2h 35m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 721 Depart at 9:15am from Chicago (ORD) Fly for 2h 35m Arrive at 12:50pm in Boston (BOS)
US$258

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

11:46am - 3:23pm
Thu May 29th 2025

2h 37m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 399 Depart at 11:46am from Chicago (ORD) Fly for 2h 37m Arrive at 3:23pm in Boston (BOS)
US$258

6:00am - 7:58am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Thu May 29th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$267

3:05pm - 5:02pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1504 Depart at 3:05pm from Boston (BOS) Fly for 2h 57m Arrive at 5:02pm in Chicago (ORD)

Stay in Chicago for 7 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$267

9:54am - 11:51am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 378 Depart at 9:54am from Boston (BOS) Fly for 2h 57m Arrive at 11:51am in Chicago (ORD)

Stay in Chicago for 7 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$267

7:45am - 9:42am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 278 Depart at 7:45am from Boston (BOS) Fly for 2h 57m Arrive at 9:42am in Chicago (ORD)

Stay in Chicago for 7 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$267

6:00am - 7:57am
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 57m Arrive at 7:57am in Chicago (ORD)

Stay in Chicago for 7 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$267

10:45am - 12:42pm
Tue May 20th 2025

2h 57m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Tue May 20th 2025 United Airlines · UA 1485 Depart at 10:45am from Boston (BOS) Fly for 2h 57m Arrive at 12:42pm in Chicago (ORD)

Stay in Chicago for 7 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$269

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Thu May 29th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 6 nights

Thu May 29th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$269

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Thu May 29th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 6 nights

Thu May 29th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$269

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Thu May 29th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$269

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Thu May 29th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$269

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Thu May 29th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$269

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Thu May 29th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$269

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Thu May 29th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$269

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Thu May 29th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$269

7:45am - 9:43am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Thu May 29th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1857 Depart at 7:45am from Boston (BOS) Fly for 2h 58m Arrive at 9:43am in Chicago (ORD)

Stay in Chicago for 6 nights

Thu May 29th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$269

6:00am - 7:58am
Fri May 23rd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 6 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$269

7:45am - 9:43am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Thu May 29th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1857 Depart at 7:45am from Boston (BOS) Fly for 2h 58m Arrive at 9:43am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$269

6:00am - 7:58am
Fri May 23rd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

7:54pm - 11:21pm
Fri May 30th 2025

2h 27m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Fri May 30th 2025 United Airlines · UA 2444 Depart at 7:54pm from Chicago (ORD) Fly for 2h 27m Arrive at 11:21pm in Boston (BOS)
US$269

7:45am - 9:43am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Thu May 29th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1857 Depart at 7:45am from Boston (BOS) Fly for 2h 58m Arrive at 9:43am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$269

6:00am - 7:58am
Fri May 23rd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

9:30pm - 12:59am
Fri May 30th 2025

2h 29m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 1414 Depart at 6:00am from Boston (BOS) Fly for 2h 58m Arrive at 7:58am in Chicago (ORD)

Stay in Chicago for 7 nights

Fri May 30th 2025 United Airlines · UA 1779 Depart at 9:30pm from Chicago (ORD) Fly for 2h 29m Arrive at 12:59am in Boston (BOS)
US$269

7:45am - 9:43am
Thu May 22nd 2025

2h 58m
Boston (BOS) → Chicago (ORD)

Direct

3:40pm - 7:10pm
Thu May 29th 2025

2h 30m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1857 Depart at 7:45am from Boston (BOS) Fly for 2h 58m Arrive at 9:43am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 1677 Depart at 3:40pm from Chicago (ORD) Fly for 2h 30m Arrive at 7:10pm in Boston (BOS)
US$269

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Thu May 29th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$269

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

2:25pm - 6:03pm
Thu May 29th 2025

2h 38m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 7 nights

Thu May 29th 2025 United Airlines · UA 580 Depart at 2:25pm from Chicago (ORD) Fly for 2h 38m Arrive at 6:03pm in Boston (BOS)
US$269

3:18pm - 5:10pm
Sat May 24th 2025

2h 52m
Boston (BOS) → Chicago (ORD)

Direct

6:20pm - 9:59pm
Tue May 27th 2025

2h 39m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1504 Depart at 3:18pm from Boston (BOS) Fly for 2h 52m Arrive at 5:10pm in Chicago (ORD)

Stay in Chicago for 3 nights

Tue May 27th 2025 United Airlines · UA 1989 Depart at 6:20pm from Chicago (ORD) Fly for 2h 39m Arrive at 9:59pm in Boston (BOS)
US$302

12:30pm - 2:21pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Thu May 29th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1732 Depart at 12:30pm from Boston (BOS) Fly for 2h 51m Arrive at 2:21pm in Chicago (ORD)

Stay in Chicago for 6 nights

Thu May 29th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$405

11:02am - 12:53pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Mon May 26th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 3 nights

Mon May 26th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$405

9:35am - 11:26am
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Mon May 26th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 3 nights

Mon May 26th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$420

11:02am - 12:53pm
Fri May 23rd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 345 Depart at 11:02am from Boston (BOS) Fly for 2h 51m Arrive at 12:53pm in Chicago (ORD)

Stay in Chicago for 6 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$420

12:30pm - 2:21pm
Fri May 23rd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 1732 Depart at 12:30pm from Boston (BOS) Fly for 2h 51m Arrive at 2:21pm in Chicago (ORD)

Stay in Chicago for 6 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$438

12:14pm - 2:05pm
Sat May 24th 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Mon May 26th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Sat May 24th 2025 United Airlines · UA 1732 Depart at 12:14pm from Boston (BOS) Fly for 2h 51m Arrive at 2:05pm in Chicago (ORD)

Stay in Chicago for 1 night

Mon May 26th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$438

12:30pm - 2:21pm
Thu May 22nd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Mon May 26th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Thu May 22nd 2025 United Airlines · UA 1732 Depart at 12:30pm from Boston (BOS) Fly for 2h 51m Arrive at 2:21pm in Chicago (ORD)

Stay in Chicago for 3 nights

Mon May 26th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)
US$457

9:35am - 11:26am
Fri May 23rd 2025

2h 51m
Boston (BOS) → Chicago (ORD)

Direct

6:30am - 9:56am
Fri May 30th 2025

2h 26m
Chicago (ORD) → Boston (BOS)

Direct

Fri May 23rd 2025 United Airlines · UA 378 Depart at 9:35am from Boston (BOS) Fly for 2h 51m Arrive at 11:26am in Chicago (ORD)

Stay in Chicago for 6 nights

Fri May 30th 2025 United Airlines · UA 2104 Depart at 6:30am from Chicago (ORD) Fly for 2h 26m Arrive at 9:56am in Boston (BOS)

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 Boston to Chicago (BOS to ORD)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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