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 to Chicago flight status
| Flight | Origin | Destination | Departure | Arrival | Equip |
|---|---|---|---|---|---|
| WN378 | Boston (BOS) | Chicago (MDW) | 8:15 a.m. | 10:50 a.m. | B38M |
| WN2414 | Boston (BOS) | Chicago (MDW) | 3:05 p.m. | 6 p.m. | B38M |
| WN2756 | Boston (BOS) | Chicago (MDW) | 7:35 p.m. | 9:10 p.m. | B737 |
| WN3060 | Boston (BOS) | Chicago (MDW) | 5:35 p.m. | 7:10 p.m. | B738 |
| WN1001 | Boston (BOS) | Chicago (MDW) | 11:10 a.m. | 5 p.m. | B737 |
| WN353 | Boston (BOS) | Chicago (MDW) | 8:45 p.m. | 8:55 p.m. | B737 |
| WN670 | Boston (BOS) | Chicago (MDW) | 3:40 p.m. | 4:35 p.m. | B738 |
| WN6449 | Boston (BOS) | Chicago (MDW) | 6:45 p.m. | 8:20 p.m. | B737 |
| DL8937 | Boston (BOS) | Chicago (MDW) | 12:15 a.m. | 1:13 a.m. | B752 |
| WN5758 | Boston (BOS) | Chicago (MDW) | 8:15 p.m. | 11 p.m. | B738 |
| WN4621 | Boston (BOS) | Chicago (MDW) | 3:10 p.m. | 5:50 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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