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Chicago → Boston

Dec 9, 2026 · return Dec 23, 2026

MDW → BOS1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Wed, Dec 9 – Wed, Dec 23

Southwest Airlines
1:40 pmMDW
7h 5m
STL · 3h 15m
9:45 pmBOS
Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Wed, Dec 23

Delta Air Lines
1:31 pmMDW
6h 20m
DTW · 3h 8m
8:51 pmBOS
Delta Air Lines
1:04 pmBOS
5h 57m
DTW · 2h 21m
6:01 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Wed, Dec 23

Southwest Airlines
5:25 pmMDW
6h 15m
BNA · 2h 20m
12:40 am+1BOS
Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Wed, Dec 23

Southwest Airlines
2:30 pmMDW
5h 50m
BWI · 2h 30m
9:20 pmBOS
Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Wed, Dec 23

Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS
Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Dec 9 – Wed, Dec 23

Delta Air Lines
10:24 amMDW
5h 37m
MSP · 1h
5:01 pmBOS
Delta Air Lines
1:04 pmBOS
5h 57m
DTW · 2h 21m
6:01 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ BOS

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-09 → 2026-12-23Southwest AirlinesWN3092 + WN4431 / WN819 + WN287$316.252026-10-29T01:29:04Z
2026-12-09 → 2026-12-23Delta Air LinesDL4688 + DL1707 / DL2222 + DL4677$448.502026-10-29T01:29:04Z
2026-12-09 → 2026-12-23Southwest AirlinesWN2897 + WN497 / WN819 + WN287$316.252026-10-29T01:29:04Z
2026-12-09 → 2026-12-23Southwest AirlinesWN14 + WN4024 / WN819 + WN287$316.252026-10-29T01:29:04Z
2026-12-09 → 2026-12-23Southwest AirlinesWN2900 / WN819 + WN287$323.752026-10-29T01:29:04Z
2026-12-09 → 2026-12-23Delta Air LinesDL5469 + DL2558 / DL2222 + DL4677$448.502026-10-29T01:29:04Z

2026-12-09 → 2026-12-23 · $316.25

  • Southwest Airlines WN3092 / WN4431: MDW 2026-12-09 13:40:00 → BOS 2026-12-09 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3092: MDW 2026-12-09 13:40:00 → STL 2026-12-09 14:55:00; layover at STL: 195 minutes.
    • WN4431: STL 2026-12-09 18:10:00 → BOS 2026-12-09 21:45:00.
  • Southwest Airlines WN819 / WN287: BOS 2026-12-23 05:35:00 → MDW 2026-12-23 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-23 05:35:00 → STL 2026-12-23 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-23 10:55:00 → MDW 2026-12-23 12:05:00.

2026-12-09 → 2026-12-23 · $448.50

  • Delta Air Lines DL4688 / DL1707: MDW 2026-12-09 13:31:00 → BOS 2026-12-09 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
    • DL4688: MDW 2026-12-09 13:31:00 → DTW 2026-12-09 15:44:00; layover at DTW: 188 minutes.
    • DL1707: DTW 2026-12-09 18:52:00 → BOS 2026-12-09 20:51:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-23 13:04:00 → MDW 2026-12-23 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-23 13:04:00 → DTW 2026-12-23 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-23 17:40:00 → MDW 2026-12-23 18:01:00.

2026-12-09 → 2026-12-23 · $316.25

  • Southwest Airlines WN2897 / WN497: MDW 2026-12-09 17:25:00 → BOS 2026-12-10 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
    • WN2897: MDW 2026-12-09 17:25:00 → BNA 2026-12-09 18:50:00; layover at BNA: 140 minutes.
    • WN497: BNA 2026-12-09 21:10:00 → BOS 2026-12-10 00:40:00.
  • Southwest Airlines WN819 / WN287: BOS 2026-12-23 05:35:00 → MDW 2026-12-23 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-23 05:35:00 → STL 2026-12-23 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-23 10:55:00 → MDW 2026-12-23 12:05:00.

2026-12-09 → 2026-12-23 · $316.25

  • Southwest Airlines WN14 / WN4024: MDW 2026-12-09 14:30:00 → BOS 2026-12-09 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN14: MDW 2026-12-09 14:30:00 → BWI 2026-12-09 17:15:00; layover at BWI: 150 minutes.
    • WN4024: BWI 2026-12-09 19:45:00 → BOS 2026-12-09 21:20:00.
  • Southwest Airlines WN819 / WN287: BOS 2026-12-23 05:35:00 → MDW 2026-12-23 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-23 05:35:00 → STL 2026-12-23 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-23 10:55:00 → MDW 2026-12-23 12:05:00.

2026-12-09 → 2026-12-23 · $323.75

  • Southwest Airlines WN2900: MDW 2026-12-09 13:15:00 → BOS 2026-12-09 16:20:00; nonstop; 125 minutes. Local airport times.
  • Southwest Airlines WN819 / WN287: BOS 2026-12-23 05:35:00 → MDW 2026-12-23 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-23 05:35:00 → STL 2026-12-23 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-23 10:55:00 → MDW 2026-12-23 12:05:00.

2026-12-09 → 2026-12-23 · $448.50

  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-09 10:24:00 → BOS 2026-12-09 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-09 10:24:00 → MSP 2026-12-09 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-09 13:09:00 → BOS 2026-12-09 17:01:00.
  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-23 13:04:00 → MDW 2026-12-23 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-23 13:04:00 → DTW 2026-12-23 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-23 17:40:00 → MDW 2026-12-23 18:01:00.

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