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Boston → Chicago

Dec 17, 2026 · return Dec 22, 2026

BOS → MDW1 adulteconomyRound trip

7 flight options · 3 airlines

Nonstop flights

Thu, Dec 17 – Tue, Dec 22

Southwest Airlines
7:05 amBOS
2h 45m
Nonstop
8:50 amMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Dec 17 – Tue, Dec 22

Southwest Airlines
5:55 pmBOS
2h 45m
Nonstop
7:40 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Dec 17 – Tue, Dec 22

Frontier Airlines
12:15 pmBOS
6h 32m
ATL · 1h 9m
5:47 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Dec 17 – Tue, Dec 22

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

Thu, Dec 17 – Tue, Dec 22

Southwest Airlines
7:25 amBOS
5h 50m
BWI · 1h 50m
12:15 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 pmBOS

Round-trip total · 1 adult · Taxes included

Thu, Dec 17 – Tue, Dec 22

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

Round-trip total · 1 adult · Taxes included

Thu, Dec 17 – Tue, Dec 22

Southwest Airlines
2:25 pmBOS
7h 40m
BNA · 3h 15m
9:05 pmMDW
Southwest Airlines
1:15 pmMDW
2h 5m
Nonstop
4:20 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 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 2027
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)
2026-12-17 → 2026-12-22Southwest AirlinesWN2185 / WN2900$310.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Frontier Airlines / Southwest AirlinesF93511 + F92779 / WN2900$265.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Delta Air LinesDL2222 + DL4677 / DL5469 + DL2558$402.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Southwest AirlinesWN816 / WN2900$310.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Southwest AirlinesWN1426 + WN1070 / WN2900$320.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Southwest AirlinesWN819 + WN287 / WN2900$320.502026-10-29T00:52:27Z
2026-12-17 → 2026-12-22Southwest AirlinesWN4765 + WN651 / WN2900$320.502026-10-29T00:52:27Z

2026-12-17 → 2026-12-22 · $310.50

  • Southwest Airlines WN2185: BOS 2026-12-17 07:05:00 → MDW 2026-12-17 08:50:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-17 → 2026-12-22 · $265.50

  • Frontier Airlines F93511 / F92779: BOS 2026-12-17 12:15:00 → MDW 2026-12-17 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
    • F93511: BOS 2026-12-17 12:15:00 → ATL 2026-12-17 15:36:00; layover at ATL: 69 minutes.
    • F92779: ATL 2026-12-17 16:45:00 → MDW 2026-12-17 17:47:00.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-17 → 2026-12-22 · $402.50

  • Delta Air Lines DL2222 / DL4677: BOS 2026-12-17 13:04:00 → MDW 2026-12-17 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
    • DL2222: BOS 2026-12-17 13:04:00 → DTW 2026-12-17 15:19:00; layover at DTW: 141 minutes.
    • DL4677: DTW 2026-12-17 17:40:00 → MDW 2026-12-17 18:01:00.
  • Delta Air Lines DL5469 / DL2558: MDW 2026-12-22 10:24:00 → BOS 2026-12-22 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
    • DL5469: MDW 2026-12-22 10:24:00 → MSP 2026-12-22 12:09:00; layover at MSP: 60 minutes.
    • DL2558: MSP 2026-12-22 13:09:00 → BOS 2026-12-22 17:01:00.

2026-12-17 → 2026-12-22 · $310.50

  • Southwest Airlines WN816: BOS 2026-12-17 17:55:00 → MDW 2026-12-17 19:40:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-17 → 2026-12-22 · $320.50

  • Southwest Airlines WN1426 / WN1070: BOS 2026-12-17 07:25:00 → MDW 2026-12-17 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
    • WN1426: BOS 2026-12-17 07:25:00 → BWI 2026-12-17 09:15:00; layover at BWI: 110 minutes.
    • WN1070: BWI 2026-12-17 11:05:00 → MDW 2026-12-17 12:15:00.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-17 → 2026-12-22 · $320.50

  • Southwest Airlines WN819 / WN287: BOS 2026-12-17 05:35:00 → MDW 2026-12-17 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
    • WN819: BOS 2026-12-17 05:35:00 → STL 2026-12-17 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-12-17 10:55:00 → MDW 2026-12-17 12:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

2026-12-17 → 2026-12-22 · $320.50

  • Southwest Airlines WN4765 / WN651: BOS 2026-12-17 14:25:00 → MDW 2026-12-17 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
    • WN4765: BOS 2026-12-17 14:25:00 → BNA 2026-12-17 16:15:00; layover at BNA: 195 minutes.
    • WN651: BNA 2026-12-17 19:30:00 → MDW 2026-12-17 21:05:00.
  • Southwest Airlines WN2900: MDW 2026-12-22 13:15:00 → BOS 2026-12-22 16:20:00; nonstop; 125 minutes. Local airport times.

More dates for this route