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Chicago → Miami

Dec 13, 2026 · return Dec 18, 2026

MDW → MIA1 adulteconomyRound trip

6 flight options · 1 airline

One-stop flights

Sun, Dec 13 – Fri, Dec 18

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

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Fri, Dec 18

Southwest Airlines
4:25 pmMDW
4h 50m
MCO · 1h
10:15 pmMIA
Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Fri, Dec 18

Southwest Airlines
7:40 amMDW
6h 25m
PIT · 2h 25m
3:05 pmMIA
Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Fri, Dec 18

Southwest Airlines
7:35 amMDW
6h
MCI · 1h 30m
2:35 pmMIA
Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Fri, Dec 18

Southwest Airlines
5:25 pmMDW
5h 25m
BNA · 1h 40m
11:50 pmMIA
Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Fri, Dec 18

Southwest Airlines
12:55 pmMDW
3h
Nonstop
4:55 pmMIA
Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ MIA

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)
2026-12-13 → 2026-12-18Southwest AirlinesWN2737 + WN4943 / WN1425 + WN1070$275.002026-10-29T01:29:10Z
2026-12-13 → 2026-12-18Southwest AirlinesWN1908 + WN2643 / WN1425 + WN1070$275.002026-10-29T01:29:10Z
2026-12-13 → 2026-12-18Southwest AirlinesWN3002 + WN301 / WN1425 + WN1070$275.002026-10-29T01:29:10Z
2026-12-13 → 2026-12-18Southwest AirlinesWN2959 + WN833 / WN1425 + WN1070$275.002026-10-29T01:29:10Z
2026-12-13 → 2026-12-18Southwest AirlinesWN2897 + WN4284 / WN1425 + WN1070$275.002026-10-29T01:29:10Z
2026-12-13 → 2026-12-18Southwest AirlinesWN1399 / WN1425 + WN1070$282.502026-10-29T01:29:10Z

2026-12-13 → 2026-12-18 · $275.00

  • Southwest Airlines WN2737 / WN4943: MDW 2026-12-13 11:30:00 → MIA 2026-12-13 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-12-13 11:30:00 → STL 2026-12-13 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-12-13 15:25:00 → MIA 2026-12-13 19:00:00.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-13 → 2026-12-18 · $275.00

  • Southwest Airlines WN1908 / WN2643: MDW 2026-12-13 16:25:00 → MIA 2026-12-13 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
    • WN1908: MDW 2026-12-13 16:25:00 → MCO 2026-12-13 20:00:00; layover at MCO: 60 minutes.
    • WN2643: MCO 2026-12-13 21:00:00 → MIA 2026-12-13 22:15:00.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-13 → 2026-12-18 · $275.00

  • Southwest Airlines WN3002 / WN301: MDW 2026-12-13 07:40:00 → MIA 2026-12-13 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
    • WN3002: MDW 2026-12-13 07:40:00 → PIT 2026-12-13 10:00:00; layover at PIT: 145 minutes.
    • WN301: PIT 2026-12-13 12:25:00 → MIA 2026-12-13 15:05:00.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-13 → 2026-12-18 · $275.00

  • Southwest Airlines WN2959 / WN833: MDW 2026-12-13 07:35:00 → MIA 2026-12-13 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
    • WN2959: MDW 2026-12-13 07:35:00 → MCI 2026-12-13 09:05:00; layover at MCI: 90 minutes.
    • WN833: MCI 2026-12-13 10:35:00 → MIA 2026-12-13 14:35:00.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-13 → 2026-12-18 · $275.00

  • Southwest Airlines WN2897 / WN4284: MDW 2026-12-13 17:25:00 → MIA 2026-12-13 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
    • WN2897: MDW 2026-12-13 17:25:00 → BNA 2026-12-13 18:50:00; layover at BNA: 100 minutes.
    • WN4284: BNA 2026-12-13 20:30:00 → MIA 2026-12-13 23:50:00.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

2026-12-13 → 2026-12-18 · $282.50

  • Southwest Airlines WN1399: MDW 2026-12-13 12:55:00 → MIA 2026-12-13 16:55:00; nonstop; 180 minutes. Local airport times.
  • Southwest Airlines WN1425 / WN1070: MIA 2026-12-18 06:30:00 → MDW 2026-12-18 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-12-18 06:30:00 → BWI 2026-12-18 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-12-18 11:05:00 → MDW 2026-12-18 12:15:00.

More dates for this route