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Cheap flights from Chicago to Boston

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

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

Chicago to Boston flight schedules

Flight Departure Date Arrival Date Price Duration Number of stops Updated
Chicago (CHI) - Boston (BOS) 2024-07-28 2024-08-02 182 USD 26 hours 55 minutes Connection 2024-05-25T17:38:25
Chicago (CHI) - Boston (BOS) 2024-06-16 2024-06-19 214 USD 17 hours 6 minutes Connection 2024-05-27T08:36:11
Chicago (CHI) - Boston (BOS) 2024-08-06 2024-08-14 220 USD 16 hours 18 minutes Connection 2024-05-27T17:26:05
Chicago (CHI) - Boston (BOS) 2024-08-06 2024-08-20 220 USD 12 hours 28 minutes Connection 2024-05-26T17:57:23
Chicago (CHI) - Boston (BOS) 2024-08-07 2024-08-20 220 USD 16 hours 19 minutes Connection 2024-05-26T22:29:11
Chicago (CHI) - Boston (BOS) 2024-08-21 2024-08-27 220 USD 16 hours 19 minutes Connection 2024-05-25T22:11:55
Chicago (CHI) - Boston (BOS) 2024-08-02 2024-08-06 222 USD 8 hours 7 minutes Connection 2024-05-26T21:47:35
Chicago (CHI) - Boston (BOS) 2024-08-02 2024-08-13 222 USD 8 hours 15 minutes Connection 2024-05-25T01:26:56
Chicago (CHI) - Boston (BOS) 2024-08-02 2024-08-14 222 USD 8 hours 13 minutes Connection 2024-05-25T01:24:58
Chicago (CHI) - Boston (BOS) 2024-08-03 2024-08-06 222 USD 8 hours 6 minutes Connection 2024-05-27T17:47:11
Chicago (CHI) - Boston (BOS) 2024-08-09 2024-08-13 222 USD 10 hours 54 minutes Connection 2024-05-25T16:53:11
Chicago (CHI) - Boston (BOS) 2024-08-10 2024-08-13 222 USD 8 hours 6 minutes Connection 2024-05-26T22:49:05
Chicago (CHI) - Boston (BOS) 2024-08-10 2024-08-14 222 USD 8 hours 6 minutes Connection 2024-05-26T13:40:24
Chicago (CHI) - Boston (BOS) 2024-08-12 2024-08-14 222 USD 7 hours 43 minutes Connection 2024-05-24T23:25:23
Chicago (CHI) - Boston (BOS) 2024-08-17 2024-08-20 222 USD 6 hours 51 minutes Connection 2024-05-25T01:14:44
Chicago (CHI) - Boston (BOS) 2024-08-19 2024-08-21 222 USD 7 hours 43 minutes Connection 2024-05-24T10:34:09
Chicago (CHI) - Boston (BOS) 2024-08-19 2024-08-29 222 USD 8 hours 6 minutes Connection 2024-05-27T19:29:05
Chicago (CHI) - Boston (BOS) 2024-08-22 2024-08-27 222 USD 8 hours 27 minutes Connection 2024-05-26T19:36:16
Chicago (CHI) - Boston (BOS) 2024-08-24 2024-08-27 222 USD 6 hours 45 minutes Connection 2024-05-24T16:01:42
Chicago (CHI) - Boston (BOS) 2024-08-24 2024-08-28 222 USD 6 hours 45 minutes Connection 2024-05-24T16:02:14
Chicago (CHI) - Boston (BOS) 2024-07-27 2024-08-06 222 USD 8 hours 6 minutes Connection 2024-05-26T13:01:51
Chicago (CHI) - Boston (BOS) 2024-07-27 2024-08-20 222 USD 8 hours 7 minutes Connection 2024-05-27T20:34:58
Chicago (CHI) - Boston (BOS) 2024-06-28 2024-07-02 222 USD 8 hours 22 minutes Connection 2024-05-26T21:33:04
Chicago (CHI) - Boston (BOS) 2024-06-29 2024-07-02 222 USD 11 hours 34 minutes Connection 2024-05-26T20:50:29
Chicago (CHI) - Boston (BOS) 2024-08-08 2024-08-20 230 USD 12 hours 28 minutes Connection 2024-05-26T22:26:51
Chicago (CHI) - Boston (BOS) 2024-06-04 2024-06-08 232 USD 8 hours 49 minutes Connection 2024-05-24T15:39:05
Chicago (CHI) - Boston (BOS) 2024-06-05 2024-06-11 232 USD 10 hours 38 minutes Connection 2024-05-27T21:57:11
Chicago (CHI) - Boston (BOS) 2024-06-07 2024-06-08 232 USD 8 hours 9 minutes Connection 2024-05-25T22:42:42
Chicago (CHI) - Boston (BOS) 2024-06-07 2024-06-11 232 USD 8 hours 8 minutes Connection 2024-05-26T17:45:30
Chicago (CHI) - Boston (BOS) 2024-06-07 2024-06-12 232 USD 8 hours 3 minutes Connection 2024-05-26T23:12:31

Chicago to Boston flight status

Flight Origin Destination Departure Arrival Equip
WN164 Chicago (MDW) Boston (BOS) 4:45 p.m. 6:10 p.m. B737
WN6188 Chicago (MDW) Boston (BOS) 9:40 p.m. 10:30 p.m. B737
WN615 Chicago (MDW) Boston (BOS) 8:15 a.m. 9:45 a.m. B38M
WN1808 Chicago (MDW) Boston (BOS) 3:35 p.m. 5:30 p.m. B737
WN5806 Chicago (MDW) Boston (BOS) 8:20 a.m. 9:55 a.m. B738
WN598 Chicago (MDW) Boston (BOS) 11:20 a.m. 12:40 p.m. B737
WN5826 Chicago (MDW) Boston (BOS) 2:10 p.m. 4:25 p.m. B737
WN3375 Chicago (MDW) Boston (BOS) 10:45 p.m. 12:15 a.m. B738
WN338 Chicago (MDW) Boston (BOS) 5:05 p.m. 7:25 p.m. B737
WN1238 Chicago (MDW) Boston (BOS) 5:25 a.m. 9:10 a.m. B737
WN6151 Chicago (MDW) Boston (BOS) 9:05 a.m. 12:20 p.m. B738
WN6955 Chicago (MDW) Boston (BOS) 11:30 a.m. 2:45 p.m. B737
WN9056 Chicago (MDW) Boston (BOS) None None B738
AK1087 Chicago (MDW) Boston (BOS) 11:05 a.m. 12:50 p.m.
FL1821 Chicago (MDW) Boston (BOS) 7:10 a.m. 7:50 a.m.

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