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Miami → Chicago

Dec 21, 2026 · return Dec 31, 2026

MIA → MDW1 adulteconomyRound trip

7 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
6:45 amMIA
3h 10m
Nonstop
8:55 amMDW
Southwest Airlines
7:40 amMDW
3h
Nonstop
11:40 amMIA

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
8:05 amMIA
5h 56m
DTW · 1h 34m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
6h 45m
DTW · 2h 30m
9:16 pmMIA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
6:50 amMIA
6h 15m
MCO · 2h 10m
12:05 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
3:05 pmMIA
6h 5m
PIT · 1h 55m
8:10 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
2:40 pmMIA
6h
CMH · 2h 10m
7:40 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
6:50 amMIA
3h 10m
Nonstop
9:00 amMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
11:40 amMIA
5h 38m
ATL · 1h 51m
4:18 pmMDW
Delta Air Lines
1:31 pmMDW
6h 45m
DTW · 2h 30m
9:16 pmMIA

Round-trip total · 1 adult · Taxes included

Make this trip yours

MIA ⇄ 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
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)
2026-12-21 → 2026-12-31Southwest AirlinesWN3081 / WN2383$426.252026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Delta Air LinesDL2638 + DL4688 / DL4688 + DL2548$474.382026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Southwest AirlinesWN4483 + WN2803 / WN2737 + WN4943$385.002026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Southwest AirlinesWN3046 + WN3556 / WN2737 + WN4943$385.002026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Southwest AirlinesWN1194 + WN1718 / WN2737 + WN4943$385.002026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Southwest AirlinesWN3081 / WN2737 + WN4943$406.002026-10-29T01:29:41Z
2026-12-21 → 2026-12-31Delta Air LinesDL3188 + DL1728 / DL4688 + DL2548$474.382026-10-29T01:29:41Z

2026-12-21 → 2026-12-31 · $426.25

  • Southwest Airlines WN3081: MIA 2026-12-21 06:45:00 → MDW 2026-12-21 08:55:00; nonstop; 190 minutes. Local airport times.
  • Southwest Airlines WN2383: MDW 2026-12-31 07:40:00 → MIA 2026-12-31 11:40:00; nonstop; 180 minutes. Local airport times.

2026-12-21 → 2026-12-31 · $474.38

  • Delta Air Lines DL2638 / DL4688: MIA 2026-12-21 08:05:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
    • DL2638: MIA 2026-12-21 08:05:00 → DTW 2026-12-21 11:10:00; layover at DTW: 94 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.
  • Delta Air Lines DL4688 / DL2548: MDW 2026-12-31 13:31:00 → MIA 2026-12-31 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
    • DL4688: MDW 2026-12-31 13:31:00 → DTW 2026-12-31 15:44:00; layover at DTW: 150 minutes.
    • DL2548: DTW 2026-12-31 18:14:00 → MIA 2026-12-31 21:16:00.

2026-12-21 → 2026-12-31 · $385.00

  • Southwest Airlines WN4483 / WN2803: MIA 2026-12-21 06:50:00 → MDW 2026-12-21 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
    • WN4483: MIA 2026-12-21 06:50:00 → MCO 2026-12-21 08:00:00; layover at MCO: 130 minutes.
    • WN2803: MCO 2026-12-21 10:10:00 → MDW 2026-12-21 12:05:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-12-31 11:30:00 → MIA 2026-12-31 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-12-31 15:25:00 → MIA 2026-12-31 19:00:00.

2026-12-21 → 2026-12-31 · $385.00

  • Southwest Airlines WN3046 / WN3556: MIA 2026-12-21 15:05:00 → MDW 2026-12-21 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
    • WN3046: MIA 2026-12-21 15:05:00 → PIT 2026-12-21 17:45:00; layover at PIT: 115 minutes.
    • WN3556: PIT 2026-12-21 19:40:00 → MDW 2026-12-21 20:10:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-12-31 11:30:00 → MIA 2026-12-31 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-12-31 15:25:00 → MIA 2026-12-31 19:00:00.

2026-12-21 → 2026-12-31 · $385.00

  • Southwest Airlines WN1194 / WN1718: MIA 2026-12-21 14:40:00 → MDW 2026-12-21 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
    • WN1194: MIA 2026-12-21 14:40:00 → CMH 2026-12-21 17:20:00; layover at CMH: 130 minutes.
    • WN1718: CMH 2026-12-21 19:30:00 → MDW 2026-12-21 19:40:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-12-31 11:30:00 → MIA 2026-12-31 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-12-31 15:25:00 → MIA 2026-12-31 19:00:00.

2026-12-21 → 2026-12-31 · $406.00

  • Southwest Airlines WN3081: MIA 2026-12-21 06:50:00 → MDW 2026-12-21 09:00:00; nonstop; 190 minutes. Local airport times.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-12-31 11:30:00 → MIA 2026-12-31 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-12-31 11:30:00 → STL 2026-12-31 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-12-31 15:25:00 → MIA 2026-12-31 19:00:00.

2026-12-21 → 2026-12-31 · $474.38

  • Delta Air Lines DL3188 / DL1728: MIA 2026-12-21 11:40:00 → MDW 2026-12-21 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
    • DL3188: MIA 2026-12-21 11:40:00 → ATL 2026-12-21 13:34:00; layover at ATL: 111 minutes.
    • DL1728: ATL 2026-12-21 15:25:00 → MDW 2026-12-21 16:18:00.
  • Delta Air Lines DL4688 / DL2548: MDW 2026-12-31 13:31:00 → MIA 2026-12-31 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
    • DL4688: MDW 2026-12-31 13:31:00 → DTW 2026-12-31 15:44:00; layover at DTW: 150 minutes.
    • DL2548: DTW 2026-12-31 18:14:00 → MIA 2026-12-31 21:16:00.

More dates for this route