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Boston → Chicago

Dec 8, 2026 · return Dec 13, 2026

BOS → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Tue, Dec 8 – Sun, Dec 13

Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Sun, Dec 13

Southwest Airlines
7:10 amBOS
2h 45m
Nonstop
8:55 amMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Tue, Dec 8 – Sun, Dec 13

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Sun, Dec 13

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

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Sun, Dec 13

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Sun, Dec 13

Southwest Airlines
5:35 amBOS
7h 30m
STL · 3h 15m
12:05 pmMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

Tue, Dec 8 – Sun, Dec 13

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW
Southwest Airlines
8:40 pmMDW
2h 15m
Nonstop
11:55 pmBOS

Round-trip total · 1 adult · Taxes included

Make this trip yours

BOS ⇄ MDW

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
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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 datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-08 → 2026-12-13Southwest AirlinesWN816 / WN249$270.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN249$225.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$350.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Southwest AirlinesWN4995 / WN249$270.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Southwest AirlinesWN4765 + WN651 / WN249$280.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Southwest AirlinesWN819 + WN287 / WN249$280.002026-10-29T00:52:27Z
2026-12-08 → 2026-12-13Southwest AirlinesWN1426 + WN1070 / WN249$280.002026-10-29T00:52:27Z

2026-12-08 → 2026-12-13 · $270.00

  • Southwest Airlines WN816: BOS 2026-12-08 17:55:00 → MDW 2026-12-08 19:40:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-08 → 2026-12-13 · $225.00

  • Frontier Airlines F93511 / F92779: BOS 2026-12-08 12:15:00 → MDW 2026-12-08 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-12-08 12:15:00 → ATL 2026-12-08 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-12-08 16:45:00 → MDW 2026-12-08 17:47:00.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-08 → 2026-12-13 · $350.00

  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-08 13:04:00 → MDW 2026-12-08 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-08 13:04:00 → DTW 2026-12-08 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-08 17:40:00 → MDW 2026-12-08 18:01:00.
  • 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.

2026-12-08 → 2026-12-13 · $270.00

  • Southwest Airlines WN4995: BOS 2026-12-08 07:10:00 → MDW 2026-12-08 08:55:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-08 → 2026-12-13 · $280.00

  • Southwest Airlines WN4765 / WN651: BOS 2026-12-08 14:25:00 → MDW 2026-12-08 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-12-08 14:25:00 → BNA 2026-12-08 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-12-08 19:30:00 → MDW 2026-12-08 21:05:00.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-08 → 2026-12-13 · $280.00

  • Southwest Airlines WN819 / WN287: BOS 2026-12-08 05:35:00 → MDW 2026-12-08 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-08 05:35:00 → STL 2026-12-08 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-08 10:55:00 → MDW 2026-12-08 12:05:00.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-08 → 2026-12-13 · $280.00

  • Southwest Airlines WN1426 / WN1070: BOS 2026-12-08 07:25:00 → MDW 2026-12-08 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-12-08 07:25:00 → BWI 2026-12-08 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-12-08 11:05:00 → MDW 2026-12-08 12:15:00.
  • Southwest Airlines WN249: MDW 2026-12-13 20:40:00 → BOS 2026-12-13 23:55:00; nonstop; 135 minutes. Local airport times.

More dates for this route