Boston → Chicago
Dec 21, 2026 · one way
BOS → MDW1 adulteconomyOne way
7 flight options · 3 airlines
Nonstop flights
One-stop flights
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Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-12-21 · one way | Southwest Airlines | WN2185 | $182.00 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Frontier Airlines | F93511 + F92779 | $123.50 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Delta Air Lines | DL2222 + DL4677 | $240.50 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Southwest Airlines | WN816 | $182.00 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Southwest Airlines | WN819 + WN287 | $195.00 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Southwest Airlines | WN4765 + WN651 | $195.00 | 2026-10-29T00:52:27Z |
| 2026-12-21 · one way | Southwest Airlines | WN1426 + WN1070 | $195.00 | 2026-10-29T00:52:27Z |
2026-12-21 · one way · $182.00
- Southwest Airlines WN2185: BOS 2026-12-21 07:05:00 → MDW 2026-12-21 08:50:00; nonstop; 165 minutes. Local airport times.
2026-12-21 · one way · $123.50
- Frontier Airlines F93511 / F92779: BOS 2026-12-21 12:15:00 → MDW 2026-12-21 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
- F93511: BOS 2026-12-21 12:15:00 → ATL 2026-12-21 15:36:00; layover at ATL: 69 minutes.
- F92779: ATL 2026-12-21 16:45:00 → MDW 2026-12-21 17:47:00.
2026-12-21 · one way · $240.50
- Delta Air Lines DL2222 / DL4677: BOS 2026-12-21 13:04:00 → MDW 2026-12-21 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
- DL2222: BOS 2026-12-21 13:04:00 → DTW 2026-12-21 15:19:00; layover at DTW: 141 minutes.
- DL4677: DTW 2026-12-21 17:40:00 → MDW 2026-12-21 18:01:00.
2026-12-21 · one way · $182.00
- Southwest Airlines WN816: BOS 2026-12-21 17:55:00 → MDW 2026-12-21 19:40:00; nonstop; 165 minutes. Local airport times.
2026-12-21 · one way · $195.00
- Southwest Airlines WN819 / WN287: BOS 2026-12-21 05:35:00 → MDW 2026-12-21 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
- WN819: BOS 2026-12-21 05:35:00 → STL 2026-12-21 07:40:00; layover at STL: 195 minutes.
- WN287: STL 2026-12-21 10:55:00 → MDW 2026-12-21 12:05:00.
2026-12-21 · one way · $195.00
- Southwest Airlines WN4765 / WN651: BOS 2026-12-21 14:25:00 → MDW 2026-12-21 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
- WN4765: BOS 2026-12-21 14:25:00 → BNA 2026-12-21 16:15:00; layover at BNA: 195 minutes.
- WN651: BNA 2026-12-21 19:30:00 → MDW 2026-12-21 21:05:00.
2026-12-21 · one way · $195.00
- Southwest Airlines WN1426 / WN1070: BOS 2026-12-21 07:25:00 → MDW 2026-12-21 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
- WN1426: BOS 2026-12-21 07:25:00 → BWI 2026-12-21 09:15:00; layover at BWI: 110 minutes.
- WN1070: BWI 2026-12-21 11:05:00 → MDW 2026-12-21 12:15:00.