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) 2024-05-04 2024-05-09 106 USD 24 hours 12 minutes Connection 2024-03-28T21:55:26
Boston (BOS) - Chicago (CHI) 2024-05-01 2024-05-05 107 USD 22 hours 35 minutes Connection 2024-03-28T15:20:17
Boston (BOS) - Chicago (CHI) 2024-05-04 2024-05-12 107 USD 21 hours 51 minutes Connection 2024-03-26T11:34:31
Boston (BOS) - Chicago (CHI) 2024-05-08 2024-05-12 107 USD 22 hours 35 minutes Connection 2024-03-28T13:14:10
Boston (BOS) - Chicago (CHI) 2024-04-27 2024-05-02 107 USD 24 hours 12 minutes Connection 2024-03-28T14:51:57
Boston (BOS) - Chicago (CHI) 2024-04-29 2024-05-02 107 USD 25 hours 1 minutes Connection 2024-03-27T21:17:41
Boston (BOS) - Chicago (CHI) 2024-04-09 2024-04-14 109 USD 16 hours 59 minutes Connection 2024-03-26T15:01:18
Boston (BOS) - Chicago (CHI) 2024-05-11 2024-05-12 116 USD 23 hours 37 minutes Connection 2024-03-28T22:54:20
Boston (BOS) - Chicago (CHI) 2024-04-24 2024-04-28 116 USD 24 hours 25 minutes Connection 2024-03-28T23:13:31
Boston (BOS) - Chicago (CHI) 2024-05-04 2024-05-05 117 USD 23 hours 37 minutes Connection 2024-03-28T18:18:28
Boston (BOS) - Chicago (CHI) 2024-04-27 2024-05-03 117 USD 26 hours 24 minutes Connection 2024-03-27T03:14:28
Boston (BOS) - Chicago (CHI) 2024-04-27 2024-05-12 117 USD 23 hours 37 minutes Connection 2024-03-27T19:22:00
Boston (BOS) - Chicago (CHI) 2024-05-07 2024-05-09 127 USD 23 hours 45 minutes Connection 2024-03-24T07:01:41
Boston (BOS) - Chicago (CHI) 2024-05-04 2024-05-06 131 USD 26 hours 24 minutes Connection 2024-03-28T18:52:04
Boston (BOS) - Chicago (CHI) 2024-05-08 2024-05-10 131 USD 27 hours 8 minutes Connection 2024-03-28T16:37:34
Boston (BOS) - Chicago (CHI) 2024-05-06 2024-05-12 132 USD 22 hours 40 minutes Connection 2024-03-29T04:35:51
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-06-04 137 USD 13 hours 11 minutes Connection 2024-03-27T01:25:21
Boston (BOS) - Chicago (CHI) 2024-05-03 2024-05-05 141 USD 24 hours 26 minutes Connection 2024-03-28T22:20:49
Boston (BOS) - Chicago (CHI) 2024-04-22 2024-04-25 147 USD 24 hours 54 minutes Connection 2024-03-29T03:37:06
Boston (BOS) - Chicago (CHI) 2024-04-24 2024-04-29 147 USD 27 hours 8 minutes Connection 2024-03-28T14:04:25
Boston (BOS) - Chicago (CHI) 2024-04-27 2024-04-29 147 USD 26 hours 24 minutes Connection 2024-03-27T12:23:03
Boston (BOS) - Chicago (CHI) 2024-04-03 2024-04-07 155 USD 20 hours 36 minutes Connection 2024-03-27T17:24:36
Boston (BOS) - Chicago (CHI) 2024-05-03 2024-05-06 155 USD 27 hours 13 minutes Connection 2024-03-27T10:18:51
Boston (BOS) - Chicago (CHI) 2024-05-06 2024-05-10 155 USD 27 hours 13 minutes Connection 2024-03-27T14:13:58
Boston (BOS) - Chicago (CHI) 2024-04-20 2024-04-26 157 USD 26 hours 24 minutes Connection 2024-03-26T17:06:32
Boston (BOS) - Chicago (CHI) 2024-04-22 2024-04-26 157 USD 27 hours 6 minutes Connection 2024-03-27T12:32:41
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-06-02 157 USD 26 hours 44 minutes Connection 2024-03-28T23:18:00
Boston (BOS) - Chicago (CHI) 2024-05-29 2024-06-05 157 USD 13 hours 11 minutes Connection 2024-03-27T15:14:59
Boston (BOS) - Chicago (CHI) 2024-06-17 2024-07-16 170 USD 9 hours 26 minutes Connection 2024-03-28T15:55:46
Boston (BOS) - Chicago (CHI) 2024-04-08 2024-05-07 186 USD 48 hours 28 minutes Connection 2024-03-28T15:56:54

Boston to Chicago flight status

Flight Origin Destination Departure Arrival Equip
WN2756 Boston (BOS) Chicago (MDW) 6:20 p.m. 11:30 p.m. B737
WN2414 Boston (BOS) Chicago (MDW) 1:45 p.m. 3:50 p.m. B38M
WN378 Boston (BOS) Chicago (MDW) 5:25 p.m. 8:20 p.m. B38M
WN670 Boston (BOS) Chicago (MDW) 3:25 p.m. 4:50 p.m. B738
WN1001 Boston (BOS) Chicago (MDW) 6:10 a.m. 8:45 a.m. B737
WN6449 Boston (BOS) Chicago (MDW) 4:35 p.m. 6:40 p.m. B737
WN353 Boston (BOS) Chicago (MDW) 4:05 p.m. 5:30 p.m. B737
WN3060 Boston (BOS) Chicago (MDW) 5:45 p.m. 11:05 p.m. B738
WN6496 Boston (BOS) Chicago (MDW) 3:30 p.m. 4:45 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.