Fort Myers (RSW) to Chicago (MDW), Nov 14–16, 2026: from $315 round trip

Fort Myers (RSW) to Chicago (MDW), Nov 14–16, 2026: from $315 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $315 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 14–16, 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 14–16, 2026 · 2 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $403 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $240 total · 5★ Nobu Hotel Chicago, $933 total

All hotels in Chicago

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

2026-11-14 → 2026-11-16 · Axel-exclusive $315.00

• Southwest Airlines WN1254 / WN2988: RSW 2026-11-14 11:10:00 → MDW 2026-11-14 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
  • WN1254: RSW 2026-11-14 11:10:00 → CMH 2026-11-14 13:40:00; layover at CMH: 65 minutes.
  • WN2988: CMH 2026-11-14 14:45:00 → MDW 2026-11-14 15:00:00.
• Southwest Airlines WN1051 / WN1331: MDW 2026-11-16 07:40:00 → RSW 2026-11-16 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2026-11-16 07:40:00 → BUF 2026-11-16 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2026-11-16 11:25:00 → RSW 2026-11-16 14:30:00.

2026-11-14 → 2026-11-16 · Axel-exclusive $390.00

• Delta Air Lines DL2277 / DL4688: RSW 2026-11-14 08:00:00 → MDW 2026-11-14 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
  • DL2277: RSW 2026-11-14 08:00:00 → DTW 2026-11-14 10:54:00; layover at DTW: 110 minutes.
  • DL4688: DTW 2026-11-14 12:44:00 → MDW 2026-11-14 13:01:00.
• Delta Air Lines DL2417 / DL1124: MDW 2026-11-16 13:02:00 → RSW 2026-11-16 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
  • DL2417: MDW 2026-11-16 13:02:00 → ATL 2026-11-16 16:01:00; layover at ATL: 76 minutes.
  • DL1124: ATL 2026-11-16 17:17:00 → RSW 2026-11-16 18:54:00.

2026-11-14 → 2026-11-16 · Axel-exclusive $315.00

• Southwest Airlines WN3648 / WN2694: RSW 2026-11-14 11:50:00 → MDW 2026-11-14 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
  • WN3648: RSW 2026-11-14 11:50:00 → MCI 2026-11-14 14:00:00; layover at MCI: 110 minutes.
  • WN2694: MCI 2026-11-14 15:50:00 → MDW 2026-11-14 17:10:00.
• Southwest Airlines WN1051 / WN1331: MDW 2026-11-16 07:40:00 → RSW 2026-11-16 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2026-11-16 07:40:00 → BUF 2026-11-16 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2026-11-16 11:25:00 → RSW 2026-11-16 14:30:00.

2026-11-14 → 2026-11-16 · Axel-exclusive $315.00

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

2026-11-14 → 2026-11-16 · Axel-exclusive $315.00

• Southwest Airlines WN3207 / WN726: RSW 2026-11-14 10:05:00 → MDW 2026-11-14 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
  • WN3207: RSW 2026-11-14 10:05:00 → BUF 2026-11-14 13:00:00; layover at BUF: 60 minutes.
  • WN726: BUF 2026-11-14 14:00:00 → MDW 2026-11-14 14:50:00.
• Southwest Airlines WN1051 / WN1331: MDW 2026-11-16 07:40:00 → RSW 2026-11-16 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2026-11-16 07:40:00 → BUF 2026-11-16 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2026-11-16 11:25:00 → RSW 2026-11-16 14:30:00.

2026-11-14 → 2026-11-16 · Axel-exclusive $327.50

• Southwest Airlines WN1590: RSW 2026-11-14 07:20:00 → MDW 2026-11-14 09:15:00; nonstop; 175 minutes. Local airport times.
• Southwest Airlines WN1051 / WN1331: MDW 2026-11-16 07:40:00 → RSW 2026-11-16 14:30:00; 1 stop(s) via BUF; 350 minutes. Local airport times.
  • WN1051: MDW 2026-11-16 07:40:00 → BUF 2026-11-16 10:05:00; layover at BUF: 80 minutes.
  • WN1331: BUF 2026-11-16 11:25:00 → RSW 2026-11-16 14:30:00.

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 13, 2026 · Return options
• Nov 15, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (MDW) · Nov 14, 2026 · return Nov 16, 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.
• 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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