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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) 2026-10-19 2026-10-22 209 USD 5 hours 0 minutes Direct 2026-09-24T20:27:17
Chicago (CHI) - Boston (BOS) 2026-11-20 2026-11-23 254 USD 22 hours 10 minutes Connection 2026-09-27T18:50:11
Chicago (CHI) - Boston (BOS) 2026-10-15 2026-10-15 268 USD 5 hours 5 minutes Direct 2026-09-28T01:00:21
Chicago (CHI) - Boston (BOS) 2026-11-21 2026-11-23 271 USD 22 hours 10 minutes Connection 2026-09-27T02:37:34
Chicago (CHI) - Boston (BOS) 2026-11-17 2026-11-24 286 USD 5 hours 5 minutes Direct 2026-09-27T02:26:36
Chicago (CHI) - Boston (BOS) 2026-11-21 2026-11-22 292 USD 17 hours 41 minutes Connection 2026-09-27T02:37:11
Chicago (CHI) - Boston (BOS) 2026-11-22 2026-11-23 305 USD 5 hours 5 minutes Direct 2026-09-27T02:35:45
Chicago (CHI) - Boston (BOS) 2026-10-25 2026-10-30 337 USD 4 hours 50 minutes Direct 2026-09-26T17:04:02
Chicago (CHI) - Boston (BOS) 2027-04-16 2027-04-30 340 USD 5 hours 0 minutes Direct 2026-09-27T19:43:46
Chicago (CHI) - Boston (BOS) 2026-11-22 2026-11-24 352 USD 5 hours 5 minutes Direct 2026-09-27T02:27:06
Chicago (CHI) - Boston (BOS) 2026-09-29 2026-10-02 370 USD 5 hours 0 minutes Direct 2026-09-25T01:11:53
Chicago (CHI) - Boston (BOS) 2026-09-29 2026-10-01 371 USD 0 minutes Direct 2026-09-28T00:00:00
Chicago (CHI) - Boston (BOS) 2026-09-29 2026-09-30 372 USD 5 hours 0 minutes Direct 2026-09-25T01:11:34
Chicago (CHI) - Boston (BOS) 2026-10-23 2026-10-25 406 USD 4 hours 55 minutes Direct 2026-09-22T23:04:21
Chicago (CHI) - Boston (BOS) 2026-10-16 2026-10-18 445 USD 4 hours 55 minutes Direct 2026-09-28T01:00:33
Chicago (CHI) - Boston (BOS) 2026-10-05 2026-10-18 467 USD 4 hours 55 minutes Direct 2026-09-28T01:01:00
Chicago (CHI) - Boston (BOS) 2026-10-06 2026-10-18 468 USD 4 hours 55 minutes Direct 2026-09-28T01:00:55

Chicago to Boston flight status

Flight Origin Destination Departure Arrival Equip
WN615 Chicago (MDW) Boston (BOS) 11:45 a.m. 4 p.m. B38M
WN164 Chicago (MDW) Boston (BOS) 3:20 p.m. 4:35 p.m. B737
WN1808 Chicago (MDW) Boston (BOS) 7:45 p.m. 8:30 p.m. B737
WN3375 Chicago (MDW) Boston (BOS) 10 a.m. 12:20 p.m. B738
WN1238 Chicago (MDW) Boston (BOS) 1 p.m. 4:25 p.m. B737
WN338 Chicago (MDW) Boston (BOS) 5:40 p.m. 8 p.m. B737
WN5806 Chicago (MDW) Boston (BOS) 8:30 a.m. 10:05 a.m. B738
WN6188 Chicago (MDW) Boston (BOS) 8:30 p.m. 9:20 p.m. B737
WN5826 Chicago (MDW) Boston (BOS) 2:10 p.m. 4:25 p.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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