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Fort Myers → Chicago

Dec 13, 2026 · return Dec 27, 2026

RSW → MDW1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
1:05 pmRSW
2h 55m
Nonstop
3:00 pmMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
7:20 amRSW
2h 55m
Nonstop
9:15 amMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

One-stop flights

Sun, Dec 13 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
10:05 amRSW
5h 45m
BUF · 1h
2:50 pmMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
11:50 amRSW
6h 20m
MCI · 1h 50m
5:10 pmMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
10:35 amRSW
6h 40m
BNA · 3h
4:15 pmMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Sun, Dec 13 – Sun, Dec 27

Southwest Airlines
11:10 amRSW
4h 50m
CMH · 1h 5m
3:00 pmMDW
Southwest Airlines
3:05 pmMDW
2h 45m
Nonstop
6:50 pmRSW

Round-trip total · 1 adult · Taxes included

Make this trip yours

RSW ⇄ 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)
2026-12-13 → 2026-12-27Southwest AirlinesWN2106 / WN3018$399.502026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Delta Air LinesDL2277 + DL4688 / DL2417 + DL1124$458.252026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN1590 / WN3018$399.502026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3207 + WN726 / WN3018$387.002026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN3648 + WN2694 / WN3018$387.002026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN1388 + WN2062 / WN3018$387.002026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN4492 + WN2803 / WN3018$387.002026-10-29T01:07:18Z
2026-12-13 → 2026-12-27Southwest AirlinesWN1254 + WN2988 / WN3018$387.002026-10-29T01:07:18Z

2026-12-13 → 2026-12-27 · $399.50

  • Southwest Airlines WN2106: RSW 2026-12-13 13:05:00 → MDW 2026-12-13 15:00:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $458.25

  • Delta Air Lines DL2277 / DL4688: RSW 2026-12-13 08:00:00 → MDW 2026-12-13 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
    • DL2277: RSW 2026-12-13 08:00:00 → DTW 2026-12-13 10:54:00; layover at DTW: 110 minutes.
    • DL4688: DTW 2026-12-13 12:44:00 → MDW 2026-12-13 13:01:00.
  • Delta Air Lines DL2417 / DL1124: MDW 2026-12-27 13:02:00 → RSW 2026-12-27 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
    • DL2417: MDW 2026-12-27 13:02:00 → ATL 2026-12-27 16:01:00; layover at ATL: 76 minutes.
    • DL1124: ATL 2026-12-27 17:17:00 → RSW 2026-12-27 18:54:00.

2026-12-13 → 2026-12-27 · $399.50

  • Southwest Airlines WN1590: RSW 2026-12-13 07:20:00 → MDW 2026-12-13 09:15:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $387.00

  • Southwest Airlines WN3207 / WN726: RSW 2026-12-13 10:05:00 → MDW 2026-12-13 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
    • WN3207: RSW 2026-12-13 10:05:00 → BUF 2026-12-13 13:00:00; layover at BUF: 60 minutes.
    • WN726: BUF 2026-12-13 14:00:00 → MDW 2026-12-13 14:50:00.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $387.00

  • Southwest Airlines WN3648 / WN2694: RSW 2026-12-13 11:50:00 → MDW 2026-12-13 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
    • WN3648: RSW 2026-12-13 11:50:00 → MCI 2026-12-13 14:00:00; layover at MCI: 110 minutes.
    • WN2694: MCI 2026-12-13 15:50:00 → MDW 2026-12-13 17:10:00.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $387.00

  • Southwest Airlines WN1388 / WN2062: RSW 2026-12-13 10:35:00 → MDW 2026-12-13 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
    • WN1388: RSW 2026-12-13 10:35:00 → BNA 2026-12-13 11:45:00; layover at BNA: 180 minutes.
    • WN2062: BNA 2026-12-13 14:45:00 → MDW 2026-12-13 16:15:00.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $387.00

  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-13 07:10:00 → MDW 2026-12-13 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-13 07:10:00 → MCO 2026-12-13 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-13 10:10:00 → MDW 2026-12-13 12:05:00.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-13 → 2026-12-27 · $387.00

  • Southwest Airlines WN1254 / WN2988: RSW 2026-12-13 11:10:00 → MDW 2026-12-13 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
    • WN1254: RSW 2026-12-13 11:10:00 → CMH 2026-12-13 13:40:00; layover at CMH: 65 minutes.
    • WN2988: CMH 2026-12-13 14:45:00 → MDW 2026-12-13 15:00:00.
  • Southwest Airlines WN3018: MDW 2026-12-27 15:05:00 → RSW 2026-12-27 18:50:00; nonstop; 165 minutes. Local airport times.

More dates for this route