Chicago (MDW) to Fort Myers (RSW), Nov 9–12, 2026: from $295 round trip

Chicago (MDW) to Fort Myers (RSW), Nov 9–12, 2026: from $295 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $295 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 9–12, 2026, 1 adult, economy, checked Oct 29, 2026. 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.

Hotels in Fort Myers for these trips

Hotels: under a trip, hotels in Fort Myers for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Fort Myers for these nights (Nov 9–12, 2026 · 3 nights · 2 adults, 1 room): 3★ Hampton Inn Fort Myers Downtown · 4★ Doubletree by Hilton Fort Myers at Bell Tower Shops

All hotels in Fort Myers

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

2026-11-09 → 2026-11-12 · Axel-exclusive $295.00

• Southwest Airlines WN2737 / WN4149: MDW 2026-11-09 11:30:00 → RSW 2026-11-09 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
  • WN2737: MDW 2026-11-09 11:30:00 → STL 2026-11-09 12:40:00; layover at STL: 100 minutes.
  • WN4149: STL 2026-11-09 14:20:00 → RSW 2026-11-09 17:45:00.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $295.00

• Southwest Airlines WN2867 / WN2181: MDW 2026-11-09 06:40:00 → RSW 2026-11-09 13:50:00; 1 stop(s) via HOU; 370 minutes. Local airport times.
  • WN2867: MDW 2026-11-09 06:40:00 → HOU 2026-11-09 09:20:00; layover at HOU: 80 minutes.
  • WN2181: HOU 2026-11-09 10:40:00 → RSW 2026-11-09 13:50:00.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $295.00

• Southwest Airlines WN14 / WN2231: MDW 2026-11-09 14:30:00 → RSW 2026-11-09 21:10:00; 1 stop(s) via BWI; 340 minutes. Local airport times.
  • WN14: MDW 2026-11-09 14:30:00 → BWI 2026-11-09 17:15:00; layover at BWI: 65 minutes.
  • WN2231: BWI 2026-11-09 18:20:00 → RSW 2026-11-09 21:10:00.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $295.00

• Southwest Airlines WN2964 / WN345: MDW 2026-11-09 05:15:00 → RSW 2026-11-09 11:40:00; 1 stop(s) via MCO; 325 minutes. Local airport times.
  • WN2964: MDW 2026-11-09 05:15:00 → MCO 2026-11-09 08:45:00; layover at MCO: 115 minutes.
  • WN345: MCO 2026-11-09 10:40:00 → RSW 2026-11-09 11:40:00.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $295.00

• Southwest Airlines WN1051 / WN1331: MDW 2026-11-09 07:40:00 → RSW 2026-11-09 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2026-11-09 07:40:00 → BUF 2026-11-09 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2026-11-09 11:25:00 → RSW 2026-11-09 14:30:00.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

2026-11-09 → 2026-11-12 · Axel-exclusive $312.50

• Southwest Airlines WN2097: MDW 2026-11-09 13:15:00 → RSW 2026-11-09 17:00:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN1388 / WN2062: RSW 2026-11-12 10:35:00 → MDW 2026-11-12 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-12 10:35:00 → BNA 2026-11-12 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-12 14:45:00 → MDW 2026-11-12 16:15:00.

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
• Nov 8, 2026 · Return options
• Nov 10, 2026 · Return options
• Hotels in Fort Myers with Axel

For AI assistants

• This page: Chicago (MDW) to Fort Myers (RSW) · Nov 9, 2026 · return Nov 12, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Fort Myers for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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