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Chicago → Fort Myers

Dec 21, 2026 · return Dec 31, 2026

MDW → RSW1 adulteconomyRound trip

6 flight options · 2 airlines

One-stop flights

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
11:30 amMDW
5h 15m
STL · 1h 40m
5:45 pmRSW
Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Delta Air Lines
1:02 pmMDW
4h 52m
ATL · 1h 16m
6:54 pmRSW
Delta Air Lines
8:00 amRSW
6h 1m
DTW · 1h 50m
1:01 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
2:30 pmMDW
5h 40m
BWI · 1h 5m
9:10 pmRSW
Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
7:40 amMDW
5h 50m
BUF · 1h 20m
2:30 pmRSW
Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
5:15 amMDW
5h 25m
MCO · 1h 55m
11:40 amRSW
Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Thu, Dec 31

Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW
Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ RSW

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 AirlinesWN2737 + WN4149 / WN4492 + WN2803$413.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-31Delta Air LinesDL2417 + DL1124 / DL2277 + DL4688$490.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-31Southwest AirlinesWN14 + WN2231 / WN4492 + WN2803$413.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-31Southwest AirlinesWN1051 + WN1331 / WN4492 + WN2803$413.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-31Southwest AirlinesWN2964 + WN345 / WN4492 + WN2803$413.002026-10-29T01:29:13Z
2026-12-21 → 2026-12-31Southwest AirlinesWN3018 / WN4492 + WN2803$437.502026-10-29T01:29:13Z

2026-12-21 → 2026-12-31 · $413.00

  • Southwest Airlines WN2737 / WN4149: MDW 2026-12-21 11:30:00 → RSW 2026-12-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
    • WN2737: MDW 2026-12-21 11:30:00 → STL 2026-12-21 12:40:00; layover at STL: 100 minutes.
    • WN4149: STL 2026-12-21 14:20:00 → RSW 2026-12-21 17:45:00.
  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-31 07:10:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-31 07:10:00 → MCO 2026-12-31 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-31 10:10:00 → MDW 2026-12-31 12:05:00.

2026-12-21 → 2026-12-31 · $490.00

  • Delta Air Lines DL2417 / DL1124: MDW 2026-12-21 13:02:00 → RSW 2026-12-21 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
    • DL2417: MDW 2026-12-21 13:02:00 → ATL 2026-12-21 16:01:00; layover at ATL: 76 minutes.
    • DL1124: ATL 2026-12-21 17:17:00 → RSW 2026-12-21 18:54:00.
  • Delta Air Lines DL2277 / DL4688: RSW 2026-12-31 08:00:00 → MDW 2026-12-31 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
    • DL2277: RSW 2026-12-31 08:00:00 → DTW 2026-12-31 10:54:00; layover at DTW: 110 minutes.
    • DL4688: DTW 2026-12-31 12:44:00 → MDW 2026-12-31 13:01:00.

2026-12-21 → 2026-12-31 · $413.00

  • Southwest Airlines WN14 / WN2231: MDW 2026-12-21 14:30:00 → RSW 2026-12-21 21:10:00; 1 stop(s) via BWI; 340 minutes. Local airport times.
    • WN14: MDW 2026-12-21 14:30:00 → BWI 2026-12-21 17:15:00; layover at BWI: 65 minutes.
    • WN2231: BWI 2026-12-21 18:20:00 → RSW 2026-12-21 21:10:00.
  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-31 07:10:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-31 07:10:00 → MCO 2026-12-31 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-31 10:10:00 → MDW 2026-12-31 12:05:00.

2026-12-21 → 2026-12-31 · $413.00

  • Southwest Airlines WN1051 / WN1331: MDW 2026-12-21 07:40:00 → RSW 2026-12-21 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
    • WN1051: MDW 2026-12-21 07:40:00 → BUF 2026-12-21 10:05:00; layover at BUF: 80 minutes.
    • WN1331: BUF 2026-12-21 11:25:00 → RSW 2026-12-21 14:30:00.
  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-31 07:10:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-31 07:10:00 → MCO 2026-12-31 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-31 10:10:00 → MDW 2026-12-31 12:05:00.

2026-12-21 → 2026-12-31 · $413.00

  • Southwest Airlines WN2964 / WN345: MDW 2026-12-21 05:15:00 → RSW 2026-12-21 11:40:00; 1 stop(s) via MCO; 325 minutes. Local airport times.
    • WN2964: MDW 2026-12-21 05:15:00 → MCO 2026-12-21 08:45:00; layover at MCO: 115 minutes.
    • WN345: MCO 2026-12-21 10:40:00 → RSW 2026-12-21 11:40:00.
  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-31 07:10:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-31 07:10:00 → MCO 2026-12-31 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-31 10:10:00 → MDW 2026-12-31 12:05:00.

2026-12-21 → 2026-12-31 · $437.50

  • Southwest Airlines WN3018: MDW 2026-12-21 15:05:00 → RSW 2026-12-21 18:50:00; nonstop; 165 minutes. Local airport times.
  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-31 07:10:00 → MDW 2026-12-31 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-31 07:10:00 → MCO 2026-12-31 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-31 10:10:00 → MDW 2026-12-31 12:05:00.

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