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Cheap flights from Boston to Chicago

Find cheap Chicago to Boston flights with our free search service. Compare all available fares for direct or connection flights from Chicago to Boston.

Round-trip
  • One-way
  • Round-trip
1 adult
Adults 12 years or over
1
Children 2-11 years
0
Infants 0-23 months
0
Cancel Done
Economy Class
  • Economy Class
  • Business Class
Done
Done

Boston to Chicago flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Boston (BOS) - Chicago (CHI) 2024-05-22 2024-05-29 129 USD 11 hours 57 minutes Connection 2024-04-29T19:02:18
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-05-29 129 USD 13 hours 5 minutes Connection 2024-04-28T13:59:55
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-05-29 129 USD 20 hours 34 minutes Connection 2024-04-26T01:25:57
Boston (BOS) - Chicago (CHI) 2024-05-22 2024-06-01 136 USD 12 hours 58 minutes Connection 2024-04-26T02:03:57
Boston (BOS) - Chicago (CHI) 2024-05-22 2024-05-25 141 USD 12 hours 58 minutes Connection 2024-04-26T14:34:16
Boston (BOS) - Chicago (CHI) 2024-05-04 2024-05-05 142 USD 23 hours 37 minutes Connection 2024-04-26T17:52:17
Boston (BOS) - Chicago (CHI) 2024-05-11 2024-05-12 142 USD 23 hours 37 minutes Connection 2024-04-29T15:01:19
Boston (BOS) - Chicago (CHI) 2024-05-11 2024-05-14 147 USD 26 hours 55 minutes Connection 2024-04-26T12:18:08
Boston (BOS) - Chicago (CHI) 2024-05-15 2024-05-29 147 USD 16 hours 51 minutes Connection 2024-04-28T02:37:57
Boston (BOS) - Chicago (CHI) 2024-05-22 2024-05-28 147 USD 12 hours 14 minutes Connection 2024-04-28T20:09:18
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-06-01 147 USD 14 hours 6 minutes Connection 2024-04-28T13:00:16
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-05-28 147 USD 13 hours 22 minutes Connection 2024-04-28T12:47:57
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-05-30 147 USD 22 hours 6 minutes Connection 2024-04-28T18:50:29
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-06-01 147 USD 12 hours 58 minutes Connection 2024-04-27T04:16:07
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-06-18 149 USD 13 hours 49 minutes Connection 2024-04-27T02:09:37
Boston (BOS) - Chicago (CHI) 2024-05-10 2024-05-12 155 USD 24 hours 26 minutes Connection 2024-04-26T21:16:33
Boston (BOS) - Chicago (CHI) 2024-05-22 2024-05-26 157 USD 11 hours 47 minutes Connection 2024-04-27T14:35:21
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-06-04 157 USD 13 hours 10 minutes Connection 2024-04-27T03:01:48
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-05-26 157 USD 12 hours 55 minutes Connection 2024-04-26T01:24:55
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-06-04 157 USD 12 hours 2 minutes Connection 2024-04-26T17:29:26
Boston (BOS) - Chicago (CHI) 2024-08-15 2024-08-20 166 USD 13 hours 22 minutes Connection 2024-04-26T20:20:52
Boston (BOS) - Chicago (CHI) 2024-07-10 2024-07-17 169 USD 13 hours 11 minutes Connection 2024-04-27T00:52:32
Boston (BOS) - Chicago (CHI) 2024-07-10 2024-07-24 169 USD 13 hours 11 minutes Connection 2024-04-29T17:00:36
Boston (BOS) - Chicago (CHI) 2024-05-25 2024-05-31 170 USD 26 hours 56 minutes Connection 2024-04-29T01:35:57
Boston (BOS) - Chicago (CHI) 2024-08-15 2024-08-21 173 USD 13 hours 22 minutes Connection 2024-04-26T20:26:34
Boston (BOS) - Chicago (CHI) 2024-05-20 2024-05-23 173 USD 11 hours 43 minutes Connection 2024-04-26T13:45:04
Boston (BOS) - Chicago (CHI) 2024-08-27 2024-09-03 173 USD 13 hours 22 minutes Connection 2024-04-26T16:29:18
Boston (BOS) - Chicago (CHI) 2024-08-28 2024-09-04 173 USD 13 hours 22 minutes Connection 2024-04-26T16:30:17
Boston (BOS) - Chicago (CHI) 2024-05-30 2024-06-07 175 USD 22 hours 22 minutes Connection 2024-04-26T11:49:37
Boston (BOS) - Chicago (CHI) 2024-09-30 2024-10-01 328 USD 4 hours 50 minutes Direct 2024-04-26T18:53:44

Boston to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN4621 Boston (BOS) Chicago (MDW) 6:05 p.m. 6:40 p.m. B738
WN2756 Boston (BOS) Chicago (MDW) 3 p.m. 5:25 p.m. B737
WN5198 Boston (BOS) Chicago (MDW) 6:15 p.m. 8:15 p.m. B738
WN2414 Boston (BOS) Chicago (MDW) 5:40 p.m. 11:05 p.m. B38M
WN378 Boston (BOS) Chicago (MDW) 8:30 a.m. 9:55 a.m. B38M
WN1001 Boston (BOS) Chicago (MDW) 2:10 p.m. 4:35 p.m. B737
WN670 Boston (BOS) Chicago (MDW) 2:20 p.m. 6:15 p.m. B738
WN5758 Boston (BOS) Chicago (MDW) 8:10 p.m. 9:35 p.m. B738
WN353 Boston (BOS) Chicago (MDW) 8:55 a.m. 10:20 a.m. B737
1I216 Boston (BOS) Chicago (MDW) 9 a.m. 11:42 a.m. CL60
DL8937 Boston (BOS) Chicago (MDW) 1 p.m. 3:23 p.m. B752
WN3060 Boston (BOS) Chicago (MDW) 5:45 p.m. 11:05 p.m. B738
WN6449 Boston (BOS) Chicago (MDW) 4:30 p.m. 6:35 p.m. B737
WN6496 Boston (BOS) Chicago (MDW) 4:35 p.m. 5:55 p.m. B737
WN5997 Boston (BOS) Chicago (MDW) 8:15 a.m. 9:40 a.m. B737
FL420 Boston (BOS) Chicago (MDW) 5 p.m. 12:30 a.m.
WN5514 Boston (BOS) Chicago (MDW) 5:45 p.m. 7:40 p.m. B737
WN6984 Boston (BOS) Chicago (MDW) 3:45 p.m. 5:20 p.m. B737
DY5885 Boston (BOS) Chicago (MDW) 2:50 p.m. 4:45 p.m.

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