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) 2024-05-02 2024-05-08 107 USD 24 hours 56 minutes Connection 2024-03-16T12:47:47
Chicago (CHI) - Boston (BOS) 2024-05-04 2024-05-11 107 USD 21 hours 51 minutes Connection 2024-03-19T02:54:33
Chicago (CHI) - Boston (BOS) 2024-04-08 2024-04-09 107 USD 17 hours 10 minutes Connection 2024-03-16T22:31:18
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-13 107 USD 25 hours 1 minutes Connection 2024-03-17T19:59:50
Chicago (CHI) - Boston (BOS) 2024-04-11 2024-04-17 107 USD 24 hours 49 minutes Connection 2024-03-18T02:07:38
Chicago (CHI) - Boston (BOS) 2024-05-11 2024-05-13 107 USD 22 hours 40 minutes Connection 2024-03-17T00:22:06
Chicago (CHI) - Boston (BOS) 2024-04-13 2024-04-17 107 USD 22 hours 28 minutes Connection 2024-03-16T00:49:09
Chicago (CHI) - Boston (BOS) 2024-04-15 2024-04-17 107 USD 27 hours 1 minutes Connection 2024-03-18T18:54:52
Chicago (CHI) - Boston (BOS) 2024-04-27 2024-04-29 107 USD 22 hours 40 minutes Connection 2024-03-17T18:25:56
Chicago (CHI) - Boston (BOS) 2024-04-03 2024-04-09 116 USD 17 hours 10 minutes Connection 2024-03-16T00:53:35
Chicago (CHI) - Boston (BOS) 2024-04-06 2024-04-09 116 USD 17 hours 4 minutes Connection 2024-03-17T21:43:27
Chicago (CHI) - Boston (BOS) 2024-05-05 2024-05-13 117 USD 24 hours 26 minutes Connection 2024-03-18T02:11:24
Chicago (CHI) - Boston (BOS) 2024-05-10 2024-05-13 117 USD 27 hours 13 minutes Connection 2024-03-16T19:57:39
Chicago (CHI) - Boston (BOS) 2024-04-14 2024-04-17 117 USD 24 hours 14 minutes Connection 2024-03-16T00:49:08
Chicago (CHI) - Boston (BOS) 2024-04-14 2024-04-20 117 USD 23 hours 37 minutes Connection 2024-03-16T11:11:07
Chicago (CHI) - Boston (BOS) 2024-04-02 2024-04-04 126 USD 21 hours 47 minutes Connection 2024-03-14T18:07:29
Chicago (CHI) - Boston (BOS) 2024-04-04 2024-04-09 131 USD 29 hours 40 minutes Connection 2024-03-16T15:10:54
Chicago (CHI) - Boston (BOS) 2024-04-05 2024-04-10 131 USD 22 hours 18 minutes Connection 2024-03-16T16:30:07
Chicago (CHI) - Boston (BOS) 2024-04-06 2024-04-10 131 USD 22 hours 33 minutes Connection 2024-03-16T16:30:34
Chicago (CHI) - Boston (BOS) 2024-05-06 2024-05-13 131 USD 27 hours 13 minutes Connection 2024-03-18T22:50:12
Chicago (CHI) - Boston (BOS) 2024-04-07 2024-04-10 131 USD 31 hours 27 minutes Connection 2024-03-18T23:20:10
Chicago (CHI) - Boston (BOS) 2024-05-11 2024-05-22 131 USD 18 hours 17 minutes Connection 2024-03-17T22:24:46
Chicago (CHI) - Boston (BOS) 2024-04-03 2024-04-04 140 USD 17 hours 40 minutes Connection 2024-03-16T16:32:03
Chicago (CHI) - Boston (BOS) 2024-04-04 2024-04-10 147 USD 31 hours 37 minutes Connection 2024-03-19T00:50:03
Chicago (CHI) - Boston (BOS) 2024-04-25 2024-04-27 147 USD 24 hours 12 minutes Connection 2024-03-19T00:39:36
Chicago (CHI) - Boston (BOS) 2024-04-01 2024-04-03 149 USD 20 hours 42 minutes Connection 2024-03-17T21:22:15
Chicago (CHI) - Boston (BOS) 2024-04-01 2024-04-04 149 USD 20 hours 42 minutes Connection 2024-03-17T21:22:11
Chicago (CHI) - Boston (BOS) 2024-03-28 2024-04-01 206 USD 61 hours 0 minutes Connection 2024-03-14T00:45:54
Chicago (CHI) - Boston (BOS) 2024-03-20 2024-03-27 378 USD 34 hours 31 minutes Connection 2024-03-16T19:04:26
Chicago (CHI) - Boston (BOS) 2024-03-22 2024-03-26 480 USD 11 hours 55 minutes Connection 2024-03-19T00:02:38

Chicago to Boston flight status

Flight Origin Destination Departure Arrival Equip
WN1808 Chicago (MDW) Boston (BOS) 4:05 p.m. 4:25 p.m. B737
WN3375 Chicago (MDW) Boston (BOS) 10:25 p.m. 11:55 p.m. B738
WN615 Chicago (MDW) Boston (BOS) 7 a.m. 9:10 a.m. B38M
WN598 Chicago (MDW) Boston (BOS) 2:15 p.m. 3:30 p.m. B737
WN5826 Chicago (MDW) Boston (BOS) 10:15 a.m. 12:35 p.m. B737
WN164 Chicago (MDW) Boston (BOS) 7:45 a.m. 9:20 a.m. B737
WN338 Chicago (MDW) Boston (BOS) 5:05 p.m. 7:25 p.m. B737
WN6188 Chicago (MDW) Boston (BOS) 3 p.m. 9:35 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
WN5806 Chicago (MDW) Boston (BOS) 4:20 p.m. 10:15 p.m. B738
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.