Flights from Boston (BOS) to Chicago (CHI) with Star Alliance

Start your journey with just one click

Airline

1/10

Boston

toChicago

BOS-ORD

February 28, 2025

March 4, 2025

Sold byUnited Airlines

From

167USD Price subject to changes

Viewed:2 hours ago

Roundtrip

Economy

2/10

Boston

toChicago

BOS-ORD

April 5, 2025

April 6, 2025

Sold byUnited Airlines

From

188USD Price subject to changes

Viewed:28 minutes ago

Roundtrip

Economy

3/10

Boston

toChicago

BOS-ORD

February 28, 2025

March 4, 2025

Sold byUnited Airlines

From

237USD Price subject to changes

Viewed:2 hours ago

Roundtrip

Economy

4/10

Boston

toChicago

BOS-ORD

April 5, 2025

April 6, 2025

Sold byUnited Airlines

From

258USD Price subject to changes

Viewed:28 minutes ago

Roundtrip

Economy

*Prices have been offered for round trips within the last 48 hours and might not be currently available. Not all Star Alliance Member Airlines or all fares/options are shown. Additional baggage fees, payment fees and fees for other optional services may apply. When booking, please check for restrictions on refunds, rebooking and baggage allowance that may apply. Prices may vary depending on the route and flights selected. Routings may include stopovers. Terms and conditions apply.

Weather in Chicago

Wednesday

overcast clouds

29/01/2025

4°C

29/01/2025

overcast clouds

Thursday

light rain

30/01/2025

5°C

30/01/2025

light rain

Friday

heavy intensity rain

31/01/2025

3°C

31/01/2025

heavy intensity rain

Saturday

overcast clouds

01/02/2025

1°C

01/02/2025

overcast clouds

Sunday

light rain

02/02/2025

8°C

02/02/2025

light rain

Monday

overcast clouds

03/02/2025

1°C

03/02/2025

overcast clouds

Tuesday

overcast clouds

04/02/2025

-4°C

04/02/2025

overcast clouds

Flight schedules from Boston to Chicago with Star Alliance member carriers

Please note that the flight schedules of our member carriers are subject to change on short notice. We recommend using our member airlines information page. for the latest flight updates, details on booking flexibility, as well as specific Frequent Flyer Program information.

Outbound (21)

Sort by

Boston US
BOS06:00
3h 3m
No stops
Chicago US
ORD08:03
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1414
  Boston. US
  BOS 06:00
  3h 3m
  869 Miles
  Chicago. US
  ORD 08:03
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Boston US
BOS09:30
2h 58m
No stops
Chicago US
ORD11:28
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 216
  Boston. US
  BOS 09:30
  2h 58m
  869 Miles
  Chicago. US
  ORD 11:28
  Boeing 737-800 Passenger
  Operated by United Airlines
Boston US
BOS10:57
2h 58m
No stops
Chicago US
ORD12:55
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 267
  Boston. US
  BOS 10:57
  2h 58m
  869 Miles
  Chicago. US
  ORD 12:55
  Boeing 737-800 Passenger
  Operated by United Airlines
Boston US
BOS12:10
2h 58m
No stops
Chicago US
ORD14:08
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 222
  Boston. US
  BOS 12:10
  2h 58m
  869 Miles
  Chicago. US
  ORD 14:08
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS16:43
2h 58m
No stops
Chicago US
ORD18:41
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2040
  Boston. US
  BOS 16:43
  2h 58m
  869 Miles
  Chicago. US
  ORD 18:41
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Boston US
BOS19:28
4h 47m
1 Stop
Chicago US
ORD23:15
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2136
  Boston. US
  BOS 19:28
  1h 46m
  414 Miles
  Washington. US
  IAD 21:14
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 1738
  Washington. US
  IAD 22:09
  2h 6m
  590 Miles
  Chicago. US
  ORD 23:15
  Airbus A320 Passenger
  Operated by United Airlines
Boston US
BOS05:45
4h 59m
1 Stop
Chicago US
ORD09:44
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1734
  Boston. US
  BOS 05:45
  1h 46m
  414 Miles
  Washington. US
  IAD 07:31
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 2440
  Washington. US
  IAD 08:25
  2h 19m
  590 Miles
  Chicago. US
  ORD 09:44
  Boeing 737-800 Passenger
  Operated by United Airlines
Boston US
BOS18:55
5h 2m
1 Stop
Chicago US
ORD22:57
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 521
  Boston. US
  BOS 18:55
  1h 30m
  201 Miles
  New York. US
  EWR 20:25
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1308
  New York. US
  EWR 21:25
  2h 32m
  721 Miles
  Chicago. US
  ORD 22:57
  Boeing 757-200 Passenger
  Operated by United Airlines
Boston US
BOS14:45
5h 10m
1 Stop
Chicago US
ORD18:55
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 214
  Boston. US
  BOS 14:45
  1h 43m
  414 Miles
  Washington. US
  IAD 16:28
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1117
  Washington. US
  IAD 17:36
  2h 19m
  590 Miles
  Chicago. US
  ORD 18:55
  Boeing 737-800 Passenger
  Operated by United Airlines
Boston US
BOS06:31
5h 13m
1 Stop
Chicago US
ORD10:44
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 570
  Boston. US
  BOS 06:31
  1h 27m
  201 Miles
  New York. US
  EWR 07:58
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 312
  New York. US
  EWR 09:00
  2h 44m
  721 Miles
  Chicago. US
  ORD 10:44
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS10:35
5h 13m
1 Stop
Chicago US
ORD14:48
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 592
  Boston. US
  BOS 10:35
  1h 25m
  201 Miles
  New York. US
  EWR 12:00
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 587
  New York. US
  EWR 13:07
  2h 41m
  721 Miles
  Chicago. US
  ORD 14:48
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS06:00
5h 44m
1 Stop
Chicago US
ORD10:44
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1833
  Boston. US
  BOS 06:00
  1h 29m
  201 Miles
  New York. US
  EWR 07:29
  Boeing 757-200 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 312
  New York. US
  EWR 09:00
  2h 44m
  721 Miles
  Chicago. US
  ORD 10:44
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS15:35
5h 50m
1 Stop
Chicago US
ORD20:25
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1977
  Boston. US
  BOS 15:35
  1h 24m
  201 Miles
  New York. US
  EWR 16:59
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 254
  New York. US
  EWR 18:43
  2h 42m
  721 Miles
  Chicago. US
  ORD 20:25
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Boston US
BOS09:35
5h 59m
1 Stop
Chicago US
ORD14:34
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2098
  Boston. US
  BOS 09:35
  1h 46m
  414 Miles
  Washington. US
  IAD 11:21
  Boeing 737-800 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1193
  Washington. US
  IAD 13:15
  2h 19m
  590 Miles
  Chicago. US
  ORD 14:34
  Boeing 737-800 Passenger
  Operated by United Airlines
Boston US
BOS13:50
6h 4m
1 Stop
Chicago US
ORD18:54
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 2454
  Boston. US
  BOS 13:50
  1h 25m
  201 Miles
  New York. US
  EWR 15:15
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 661
  New York. US
  EWR 17:08
  2h 46m
  721 Miles
  Chicago. US
  ORD 18:54
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS17:50
6h 7m
1 Stop
Chicago US
ORD22:57
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1606
  Boston. US
  BOS 17:50
  1h 26m
  201 Miles
  New York. US
  EWR 19:16
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
2. Flight 2United Airlines UA 1308
  New York. US
  EWR 21:25
  2h 32m
  721 Miles
  Chicago. US
  ORD 22:57
  Boeing 757-200 Passenger
  Operated by United Airlines
Boston US
BOS06:31
6h 7m
1 Stop
Chicago US
ORD11:38
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 570
  Boston. US
  BOS 06:31
  1h 27m
  201 Miles
  New York. US
  EWR 07:58
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1525
  New York. US
  EWR 10:00
  2h 38m
  721 Miles
  Chicago. US
  ORD 11:38
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Boston US
BOS09:25
6h 23m
1 Stop
Chicago US
ORD14:48
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 515
  Boston. US
  BOS 09:25
  1h 25m
  201 Miles
  New York. US
  EWR 10:50
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 587
  New York. US
  EWR 13:07
  2h 41m
  721 Miles
  Chicago. US
  ORD 14:48
  Boeing 737-900 Passenger
  Operated by United Airlines
Boston US
BOS06:00
6h 38m
1 Stop
Chicago US
ORD11:38
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1833
  Boston. US
  BOS 06:00
  1h 29m
  201 Miles
  New York. US
  EWR 07:29
  Boeing 757-200 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 1525
  New York. US
  EWR 10:00
  2h 38m
  721 Miles
  Chicago. US
  ORD 11:38
  Boeing 737 MAX 8 Passenger / BBJ MAX 8 / Boeing 737 MAX 200
  Operated by United Airlines
Boston US
BOS10:35
6h 51m
1 Stop
Chicago US
ORD16:26
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 592
  Boston. US
  BOS 10:35
  1h 25m
  201 Miles
  New York. US
  EWR 12:00
  Boeing 737-900 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 276
  New York. US
  EWR 14:45
  2h 41m
  721 Miles
  Chicago. US
  ORD 16:26
  Boeing 737 MAX 9 Passenger / BBJ MAX 9
  Operated by United Airlines
Boston US
BOS15:35
7h 8m
1 Stop
Chicago US
ORD21:43
Boston - Chicago
United Airlines
Flight Operates
1. Mon
2. Tue
3. Wed
4. Thu
5. Fri
6. Sat
7. Sun
1. Flight 1United Airlines UA 1977
  Boston. US
  BOS 15:35
  1h 24m
  201 Miles
  New York. US
  EWR 16:59
  Airbus A319 Passenger
  Operated by United Airlines
2. Flight 2United Airlines UA 546
  New York. US
  EWR 19:58
  2h 45m
  721 Miles
  Chicago. US
  ORD 21:43
  Boeing 737-900 Passenger
  Operated by United Airlines

Start your journey with just one click

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago

Boston - Chicago