Chicago → Boston
Dec 13, 2026 · one way
MDW → BOS1 adulteconomyOne way
7 flight options · 2 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) |
|---|---|---|---|---|
| 2026-12-13 · one way | Southwest Airlines | WN4113 | $155.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Delta Air Lines | DL5469 + DL2558 | $205.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Southwest Airlines | WN249 | $155.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Southwest Airlines | WN14 + WN4024 | $145.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Southwest Airlines | WN3092 + WN4431 | $145.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Southwest Airlines | WN2897 + WN497 | $145.00 | 2026-10-29T01:29:04Z |
| 2026-12-13 · one way | Delta Air Lines | DL4688 + DL1707 | $205.00 | 2026-10-29T01:29:04Z |
2026-12-13 · one way · $155.00
- Southwest Airlines WN4113: MDW 2026-12-13 07:45:00 → BOS 2026-12-13 11:00:00; nonstop; 135 minutes. Local airport times.
2026-12-13 · one way · $205.00
- Delta Air Lines DL5469 / DL2558: MDW 2026-12-13 10:24:00 → BOS 2026-12-13 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
- DL5469: MDW 2026-12-13 10:24:00 → MSP 2026-12-13 12:09:00; layover at MSP: 60 minutes.
- DL2558: MSP 2026-12-13 13:09:00 → BOS 2026-12-13 17:01:00.
2026-12-13 · one way · $155.00
- Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.
2026-12-13 · one way · $145.00
- Southwest Airlines WN14 / WN4024: MDW 2026-12-13 14:30:00 → BOS 2026-12-13 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
- WN14: MDW 2026-12-13 14:30:00 → BWI 2026-12-13 17:15:00; layover at BWI: 150 minutes.
- WN4024: BWI 2026-12-13 19:45:00 → BOS 2026-12-13 21:20:00.
2026-12-13 · one way · $145.00
- Southwest Airlines WN3092 / WN4431: MDW 2026-12-13 13:40:00 → BOS 2026-12-13 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
- WN3092: MDW 2026-12-13 13:40:00 → STL 2026-12-13 14:55:00; layover at STL: 195 minutes.
- WN4431: STL 2026-12-13 18:10:00 → BOS 2026-12-13 21:45:00.
2026-12-13 · one way · $145.00
- Southwest Airlines WN2897 / WN497: MDW 2026-12-13 17:25:00 → BOS 2026-12-14 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
- WN2897: MDW 2026-12-13 17:25:00 → BNA 2026-12-13 18:50:00; layover at BNA: 140 minutes.
- WN497: BNA 2026-12-13 21:10:00 → BOS 2026-12-14 00:40:00.
2026-12-13 · one way · $205.00
- Delta Air Lines DL4688 / DL1707: MDW 2026-12-13 13:31:00 → BOS 2026-12-13 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
- DL4688: MDW 2026-12-13 13:31:00 → DTW 2026-12-13 15:44:00; layover at DTW: 188 minutes.
- DL1707: DTW 2026-12-13 18:52:00 → BOS 2026-12-13 20:51:00.