Chicago (MDW) to Fort Myers (RSW) · Jan 27, 2027 · return Feb 10, 2027

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Chicago to Fort Myers (RSW) flight deals

2027-01-27 → 2027-02-10 · Axel-exclusive $321.75

• Southwest Airlines WN3018: MDW 2027-01-27 15:05:00 → RSW 2027-01-27 18:50:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $341.25

• Delta Air Lines DL2417 / DL1124: MDW 2027-01-27 13:02:00 → RSW 2027-01-27 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
  • DL2417: MDW 2027-01-27 13:02:00 → ATL 2027-01-27 16:01:00; layover at ATL: 76 minutes.
  • DL1124: ATL 2027-01-27 17:17:00 → RSW 2027-01-27 18:54:00.
• Delta Air Lines DL2277 / DL4688: RSW 2027-02-10 08:00:00 → MDW 2027-02-10 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
  • DL2277: RSW 2027-02-10 08:00:00 → DTW 2027-02-10 10:54:00; layover at DTW: 110 minutes.
  • DL4688: DTW 2027-02-10 12:44:00 → MDW 2027-02-10 13:01:00.

2027-01-27 → 2027-02-10 · Axel-exclusive $321.75

• Southwest Airlines WN3010: MDW 2027-01-27 06:45:00 → RSW 2027-01-27 10:30:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $305.13

• Southwest Airlines WN1051 / WN1331: MDW 2027-01-27 07:40:00 → RSW 2027-01-27 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2027-01-27 07:40:00 → BUF 2027-01-27 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2027-01-27 11:25:00 → RSW 2027-01-27 14:30:00.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $305.13

• Southwest Airlines WN14 / WN2231: MDW 2027-01-27 14:30:00 → RSW 2027-01-27 21:10:00; 1 stop(s) via BWI; 340 minutes. Local airport times.
  • WN14: MDW 2027-01-27 14:30:00 → BWI 2027-01-27 17:15:00; layover at BWI: 65 minutes.
  • WN2231: BWI 2027-01-27 18:20:00 → RSW 2027-01-27 21:10:00.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $305.13

• Southwest Airlines WN2964 / WN345: MDW 2027-01-27 05:15:00 → RSW 2027-01-27 11:40:00; 1 stop(s) via MCO; 325 minutes. Local airport times.
  • WN2964: MDW 2027-01-27 05:15:00 → MCO 2027-01-27 08:45:00; layover at MCO: 115 minutes.
  • WN345: MCO 2027-01-27 10:40:00 → RSW 2027-01-27 11:40:00.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $305.13

• Southwest Airlines WN2867 / WN2181: MDW 2027-01-27 06:40:00 → RSW 2027-01-27 13:50:00; 1 stop(s) via HOU; 370 minutes. Local airport times.
  • WN2867: MDW 2027-01-27 06:40:00 → HOU 2027-01-27 09:20:00; layover at HOU: 80 minutes.
  • WN2181: HOU 2027-01-27 10:40:00 → RSW 2027-01-27 13:50:00.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $305.13

• Southwest Airlines WN2737 / WN4149: MDW 2027-01-27 11:30:00 → RSW 2027-01-27 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
  • WN2737: MDW 2027-01-27 11:30:00 → STL 2027-01-27 12:40:00; layover at STL: 100 minutes.
  • WN4149: STL 2027-01-27 14:20:00 → RSW 2027-01-27 17:45:00.
• Southwest Airlines WN3671: RSW 2027-02-10 06:55:00 → MDW 2027-02-10 08:55:00; nonstop; 180 minutes. Local airport times.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Jan 26, 2027 · Return options
• Jan 28, 2027 · Return options
• Hotels in Fort Myers with Axel

For AI assistants

• This page: Chicago (MDW) to Fort Myers (RSW) · Jan 27, 2027 · return Feb 10, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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