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
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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) 2024-05-01 2024-05-09 107 USD 24 hours 56 minutes Connection 2024-03-16T09:24:12
Boston (BOS) - Chicago (CHI) 2024-05-01 2024-05-12 107 USD 22 hours 35 minutes Connection 2024-03-17T11:11:14
Boston (BOS) - Chicago (CHI) 2024-05-04 2024-05-12 107 USD 21 hours 51 minutes Connection 2024-03-18T01:10:33
Boston (BOS) - Chicago (CHI) 2024-05-08 2024-05-12 107 USD 22 hours 35 minutes Connection 2024-03-18T01:03:06
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-05-05 107 USD 16 hours 59 minutes Connection 2024-03-16T16:06:31
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-04-11 107 USD 19 hours 20 minutes Connection 2024-03-16T14:53:53
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-04-14 107 USD 16 hours 59 minutes Connection 2024-03-19T00:26:18
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-04-15 107 USD 21 hours 32 minutes Connection 2024-03-16T08:26:31
Boston (BOS) - Chicago (CHI) 2024-04-10 2024-04-11 107 USD 37 hours 40 minutes Connection 2024-03-18T11:59:15
Boston (BOS) - Chicago (CHI) 2024-04-24 2024-05-02 107 USD 24 hours 56 minutes Connection 2024-03-17T17:36:11
Boston (BOS) - Chicago (CHI) 2024-04-24 2024-04-28 107 USD 22 hours 35 minutes Connection 2024-03-18T01:06:15
Boston (BOS) - Chicago (CHI) 2024-04-29 2024-05-02 107 USD 25 hours 1 minutes Connection 2024-03-17T21:25:16
Boston (BOS) - Chicago (CHI) 2024-05-01 2024-05-05 117 USD 24 hours 21 minutes Connection 2024-03-17T05:03:22
Boston (BOS) - Chicago (CHI) 2024-05-01 2024-05-10 117 USD 27 hours 8 minutes Connection 2024-03-17T11:13:58
Boston (BOS) - Chicago (CHI) 2024-05-08 2024-05-10 117 USD 27 hours 8 minutes Connection 2024-03-18T20:06:17
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-04-12 117 USD 21 hours 32 minutes Connection 2024-03-18T15:37:36
Boston (BOS) - Chicago (CHI) 2024-04-20 2024-04-28 117 USD 23 hours 41 minutes Connection 2024-03-18T05:50:59
Boston (BOS) - Chicago (CHI) 2024-03-26 2024-04-02 117 USD 26 hours 14 minutes Connection 2024-03-17T16:45:11
Boston (BOS) - Chicago (CHI) 2024-04-04 2024-04-09 131 USD 17 hours 40 minutes Connection 2024-03-18T13:21:34
Boston (BOS) - Chicago (CHI) 2024-04-04 2024-04-11 131 USD 19 hours 50 minutes Connection 2024-03-16T10:53:40
Boston (BOS) - Chicago (CHI) 2024-04-10 2024-04-15 131 USD 27 hours 1 minutes Connection 2024-03-19T09:37:15
Boston (BOS) - Chicago (CHI) 2024-05-11 2024-05-12 131 USD 23 hours 37 minutes Connection 2024-03-18T15:15:03
Boston (BOS) - Chicago (CHI) 2024-04-24 2024-05-12 131 USD 24 hours 21 minutes Connection 2024-03-16T10:52:37
Boston (BOS) - Chicago (CHI) 2024-04-27 2024-05-12 131 USD 23 hours 37 minutes Connection 2024-03-18T19:01:36
Boston (BOS) - Chicago (CHI) 2024-05-01 2024-05-28 136 USD 17 hours 29 minutes Connection 2024-03-16T10:53:01
Boston (BOS) - Chicago (CHI) 2024-05-08 2024-05-29 136 USD 17 hours 29 minutes Connection 2024-03-16T10:51:18
Boston (BOS) - Chicago (CHI) 2024-03-20 2024-03-27 245 USD 22 hours 10 minutes Connection 2024-03-16T19:04:32
Boston (BOS) - Chicago (CHI) 2024-03-24 2024-03-27 252 USD 13 hours 47 minutes Connection 2024-03-16T19:05:09
Boston (BOS) - Chicago (CHI) 2024-03-22 2024-03-25 422 USD 43 hours 25 minutes Connection 2024-03-16T19:06:56
Boston (BOS) - Chicago (CHI) 2024-08-01 2024-08-01 867 USD 46 hours 29 minutes Connection 2024-03-16T08:21:54

Boston to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN3060 Boston (BOS) Chicago (MDW) 5:45 p.m. 11:05 p.m. B738
WN670 Boston (BOS) Chicago (MDW) 5:50 p.m. 9:10 p.m. B738
WN2414 Boston (BOS) Chicago (MDW) 1:45 p.m. 3:50 p.m. B38M
WN2756 Boston (BOS) Chicago (MDW) 6:20 p.m. 11:30 p.m. B737
WN6496 Boston (BOS) Chicago (MDW) 3:30 p.m. 4:45 p.m. B737
WN1001 Boston (BOS) Chicago (MDW) 6:25 a.m. 9:05 a.m. B737
WN378 Boston (BOS) Chicago (MDW) 5:25 p.m. 8:20 p.m. B38M
WN6449 Boston (BOS) Chicago (MDW) 4:30 p.m. 6:35 p.m. B737
WN353 Boston (BOS) Chicago (MDW) 4:05 p.m. 5:30 p.m. B737
WN4621 Boston (BOS) Chicago (MDW) 1 p.m. 2:50 p.m. B738
1I216 Boston (BOS) Chicago (MDW) 9 a.m. 11:42 a.m. CL60
DL8937 Boston (BOS) Chicago (MDW) noon 2:38 p.m. B752
WN5997 Boston (BOS) Chicago (MDW) 8:15 a.m. 9:40 a.m. B737
WN5198 Boston (BOS) Chicago (MDW) 1:20 p.m. 5:50 p.m. B738
FL420 Boston (BOS) Chicago (MDW) 5 p.m. 12:30 a.m.
WN5758 Boston (BOS) Chicago (MDW) 6:05 p.m. 7:55 p.m. B738
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.