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.
Boston to Chicago flight schedules
| Flight | Departure Date | Arrival Date | Price | Duration | Number of stops | Updated |
|---|---|---|---|---|---|---|
| Boston (BOS) - Chicago (CHI) | 2026-08-14 | 2026-08-14 | 187 USD | 4 hours 55 minutes | Direct | 2026-07-09T14:37:11 |
| Boston (BOS) - Chicago (CHI) | 2026-10-09 | 2026-10-09 | 414 USD | 10 hours 20 minutes | Connection | 2026-07-10T17:20:51 |
| Boston (BOS) - Chicago (CHI) | 2026-08-02 | 2026-08-02 | 423 USD | 5 hours 0 minutes | Direct | 2026-07-10T03:02:38 |
Boston to Chicago flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| WN2414 | Boston (BOS) | Chicago (MDW) | 8:45 a.m. | 10:30 a.m. | B38M |
| WN353 | Boston (BOS) | Chicago (MDW) | 8:55 a.m. | 10:25 a.m. | B737 |
| WN1001 | Boston (BOS) | Chicago (MDW) | 6:30 p.m. | 9:55 p.m. | B737 |
| WN378 | Boston (BOS) | Chicago (MDW) | 8:10 p.m. | 8:40 p.m. | B38M |
| WN4621 | Boston (BOS) | Chicago (MDW) | 3:35 p.m. | 5:30 p.m. | B738 |
| WN3060 | Boston (BOS) | Chicago (MDW) | 1:55 p.m. | 4:10 p.m. | B738 |
| WN2756 | Boston (BOS) | Chicago (MDW) | 6:15 p.m. | 8:30 p.m. | B737 |
| WN670 | Boston (BOS) | Chicago (MDW) | 1:55 p.m. | 2:55 p.m. | B738 |
| DL8937 | Boston (BOS) | Chicago (MDW) | 8:30 p.m. | 10:57 p.m. | B752 |
| WN6449 | Boston (BOS) | Chicago (MDW) | 6:45 p.m. | 8:20 p.m. | B737 |
| WN5758 | Boston (BOS) | Chicago (MDW) | 8:15 p.m. | 11 p.m. | B738 |
| WN5198 | Boston (BOS) | Chicago (MDW) | 7:45 a.m. | 3:05 p.m. | B738 |
| WN6496 | Boston (BOS) | Chicago (MDW) | 3:30 p.m. | 4:35 p.m. | B737 |
| WN5997 | Boston (BOS) | Chicago (MDW) | 8:15 a.m. | 9:40 a.m. | B737 |
| 1I216 | Boston (BOS) | Chicago (MDW) | 9 a.m. | 11:42 a.m. | CL60 |
| WN5514 | Boston (BOS) | Chicago (MDW) | 10:25 p.m. | 11:45 p.m. | B737 |
| FL420 | Boston (BOS) | Chicago (MDW) | 5 p.m. | 12:30 a.m. | |
| 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. |
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