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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) 2024-05-11 2024-05-13 99 USD 22 hours 40 minutes Connection 2024-04-23T02:27:58
Chicago (CHI) - Boston (BOS) 2024-05-18 2024-05-20 125 USD 27 hours 39 minutes Connection 2024-04-23T04:36:30
Chicago (CHI) - Boston (BOS) 2024-05-02 2024-05-16 131 USD 28 hours 54 minutes Connection 2024-04-23T05:36:21
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-13 131 USD 25 hours 1 minutes Connection 2024-04-23T16:50:36
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-18 131 USD 29 hours 21 minutes Connection 2024-04-23T00:10:11
Chicago (CHI) - Boston (BOS) 2024-05-10 2024-05-13 131 USD 27 hours 13 minutes Connection 2024-04-25T02:49:01
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-17 141 USD 29 hours 16 minutes Connection 2024-04-23T00:10:43
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-19 141 USD 28 hours 37 minutes Connection 2024-04-23T00:10:28
Chicago (CHI) - Boston (BOS) 2024-05-12 2024-05-20 141 USD 19 hours 11 minutes Connection 2024-04-23T00:16:32
Chicago (CHI) - Boston (BOS) 2024-05-17 2024-05-19 141 USD 33 hours 59 minutes Connection 2024-04-24T20:17:19
Chicago (CHI) - Boston (BOS) 2024-05-03 2024-05-04 142 USD 26 hours 24 minutes Connection 2024-04-26T15:05:44
Chicago (CHI) - Boston (BOS) 2024-05-17 2024-05-25 142 USD 26 hours 32 minutes Connection 2024-04-23T01:46:58
Chicago (CHI) - Boston (BOS) 2024-05-04 2024-05-05 144 USD 27 hours 42 minutes Connection 2024-04-23T15:32:40
Chicago (CHI) - Boston (BOS) 2024-05-06 2024-05-11 146 USD 26 hours 24 minutes Connection 2024-04-24T16:38:01
Chicago (CHI) - Boston (BOS) 2024-05-02 2024-05-06 155 USD 25 hours 1 minutes Connection 2024-04-25T18:05:40
Chicago (CHI) - Boston (BOS) 2024-05-03 2024-05-06 155 USD 27 hours 13 minutes Connection 2024-04-25T18:04:29
Chicago (CHI) - Boston (BOS) 2024-05-03 2024-05-07 157 USD 32 hours 15 minutes Connection 2024-04-23T04:48:34
Chicago (CHI) - Boston (BOS) 2024-05-16 2024-05-20 157 USD 40 hours 19 minutes Connection 2024-04-23T21:57:08
Chicago (CHI) - Boston (BOS) 2024-05-10 2024-05-12 161 USD 32 hours 15 minutes Connection 2024-04-25T14:59:58
Chicago (CHI) - Boston (BOS) 2024-05-17 2024-05-20 162 USD 36 hours 28 minutes Connection 2024-04-23T21:57:35
Chicago (CHI) - Boston (BOS) 2024-05-02 2024-05-05 164 USD 30 hours 3 minutes Connection 2024-04-23T01:33:30
Chicago (CHI) - Boston (BOS) 2024-05-03 2024-05-05 164 USD 32 hours 15 minutes Connection 2024-04-23T09:55:31
Chicago (CHI) - Boston (BOS) 2024-04-28 2024-04-29 164 USD 24 hours 30 minutes Connection 2024-04-23T04:53:00
Chicago (CHI) - Boston (BOS) 2024-05-09 2024-05-12 177 USD 30 hours 3 minutes Connection 2024-04-25T21:31:17
Chicago (CHI) - Boston (BOS) 2024-05-13 2024-05-14 177 USD 32 hours 15 minutes Connection 2024-04-23T14:32:04
Chicago (CHI) - Boston (BOS) 2024-05-02 2024-05-10 181 USD 28 hours 47 minutes Connection 2024-04-25T14:13:15
Chicago (CHI) - Boston (BOS) 2024-05-04 2024-05-09 181 USD 27 hours 42 minutes Connection 2024-04-23T19:48:59
Chicago (CHI) - Boston (BOS) 2024-06-06 2024-06-10 185 USD 27 hours 40 minutes Connection 2024-04-24T14:14:47
Chicago (CHI) - Boston (BOS) 2024-05-13 2024-05-16 205 USD 17 hours 57 minutes Connection 2024-04-21T18:06:08
Chicago (CHI) - Boston (BOS) 2024-05-20 2024-05-23 281 USD 5 hours 11 minutes Direct 2024-04-22T18:58:10

Chicago to Boston flight status

Flight Origin Destination Departure Arrival Equip
WN1808 Chicago (MDW) Boston (BOS) 3:35 p.m. 5:30 p.m. B737
WN5806 Chicago (MDW) Boston (BOS) 8:30 a.m. 10:05 a.m. B738
WN615 Chicago (MDW) Boston (BOS) 8:15 a.m. 9:45 a.m. B38M
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
WN598 Chicago (MDW) Boston (BOS) 1:30 p.m. 2:50 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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