Fort Myers (RSW) to Chicago (MDW), Nov 10–12, 2026: from $315 round trip

Fort Myers (RSW) to Chicago (MDW), Nov 10–12, 2026: from $315 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $315 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 10–12, 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 Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Nov 10–12, 2026 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $209 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $38 total · 5★ Nobu Hotel Chicago, $1,272 total

All hotels in Chicago

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

2026-11-10 → 2026-11-12 · Axel-exclusive $340.00

• Southwest Airlines WN3671: RSW 2026-11-10 06:55:00 → MDW 2026-11-10 08:55:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN2097: MDW 2026-11-12 13:15:00 → RSW 2026-11-12 17:00:00; nonstop; 165 minutes. Local airport times.

2026-11-10 → 2026-11-12 · Axel-exclusive $390.00

• Delta Air Lines DL2277 / DL4688: RSW 2026-11-10 08:00:00 → MDW 2026-11-10 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
  • DL2277: RSW 2026-11-10 08:00:00 → DTW 2026-11-10 10:54:00; layover at DTW: 110 minutes.
  • DL4688: DTW 2026-11-10 12:44:00 → MDW 2026-11-10 13:01:00.
• Delta Air Lines DL2417 / DL1124: MDW 2026-11-12 13:02:00 → RSW 2026-11-12 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
  • DL2417: MDW 2026-11-12 13:02:00 → ATL 2026-11-12 16:01:00; layover at ATL: 76 minutes.
  • DL1124: ATL 2026-11-12 17:17:00 → RSW 2026-11-12 18:54:00.

2026-11-10 → 2026-11-12 · Axel-exclusive $315.00

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

2026-11-10 → 2026-11-12 · Axel-exclusive $315.00

• Southwest Airlines WN3648 / WN2694: RSW 2026-11-10 11:50:00 → MDW 2026-11-10 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
  • WN3648: RSW 2026-11-10 11:50:00 → MCI 2026-11-10 14:00:00; layover at MCI: 110 minutes.
  • WN2694: MCI 2026-11-10 15:50:00 → MDW 2026-11-10 17:10:00.
• Southwest Airlines WN2737 / WN4149: MDW 2026-11-12 11:30:00 → RSW 2026-11-12 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
  • WN2737: MDW 2026-11-12 11:30:00 → STL 2026-11-12 12:40:00; layover at STL: 100 minutes.
  • WN4149: STL 2026-11-12 14:20:00 → RSW 2026-11-12 17:45:00.

2026-11-10 → 2026-11-12 · Axel-exclusive $315.00

• Southwest Airlines WN1254 / WN2988: RSW 2026-11-10 11:10:00 → MDW 2026-11-10 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
  • WN1254: RSW 2026-11-10 11:10:00 → CMH 2026-11-10 13:40:00; layover at CMH: 65 minutes.
  • WN2988: CMH 2026-11-10 14:45:00 → MDW 2026-11-10 15:00:00.
• Southwest Airlines WN2737 / WN4149: MDW 2026-11-12 11:30:00 → RSW 2026-11-12 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
  • WN2737: MDW 2026-11-12 11:30:00 → STL 2026-11-12 12:40:00; layover at STL: 100 minutes.
  • WN4149: STL 2026-11-12 14:20:00 → RSW 2026-11-12 17:45:00.

2026-11-10 → 2026-11-12 · Axel-exclusive $315.00

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

2026-11-10 → 2026-11-12 · Axel-exclusive $327.50

• Southwest Airlines WN3671: RSW 2026-11-10 07:00:00 → MDW 2026-11-10 08:55:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN2737 / WN4149: MDW 2026-11-12 11:30:00 → RSW 2026-11-12 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
  • WN2737: MDW 2026-11-12 11:30:00 → STL 2026-11-12 12:40:00; layover at STL: 100 minutes.
  • WN4149: STL 2026-11-12 14:20:00 → RSW 2026-11-12 17:45:00.

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 9, 2026 · Return options
• Nov 11, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (MDW) · Nov 10, 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 Chicago 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.
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