Fort Myers (RSW) to Chicago (MDW), Nov 23, 2026: from $206 one way

Fort Myers (RSW) to Chicago (MDW), Nov 23, 2026: from $206 one way on Axel, checked Oct 29, 2026. Lowest published fare: $206 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 23, 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.

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

2026-11-23 · one way · Axel-exclusive $225.00

• Southwest Airlines WN2106: RSW 2026-11-23 13:05:00 → MDW 2026-11-23 15:00:00; nonstop; 175 minutes. Local airport times.

2026-11-23 · one way · Axel-exclusive $256.25

• Delta Air Lines DL2277 / DL4688: RSW 2026-11-23 08:00:00 → MDW 2026-11-23 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
  • DL2277: RSW 2026-11-23 08:00:00 → DTW 2026-11-23 10:54:00; layover at DTW: 110 minutes.
  • DL4688: DTW 2026-11-23 12:44:00 → MDW 2026-11-23 13:01:00.

2026-11-23 · one way · Axel-exclusive $225.00

• Southwest Airlines WN1590: RSW 2026-11-23 07:20:00 → MDW 2026-11-23 09:15:00; nonstop; 175 minutes. Local airport times.

2026-11-23 · one way · Axel-exclusive $206.25

• Southwest Airlines WN1388 / WN2062: RSW 2026-11-23 10:35:00 → MDW 2026-11-23 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-11-23 10:35:00 → BNA 2026-11-23 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-11-23 14:45:00 → MDW 2026-11-23 16:15:00.

2026-11-23 · one way · Axel-exclusive $206.25

• Southwest Airlines WN3648 / WN2694: RSW 2026-11-23 11:50:00 → MDW 2026-11-23 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
  • WN3648: RSW 2026-11-23 11:50:00 → MCI 2026-11-23 14:00:00; layover at MCI: 110 minutes.
  • WN2694: MCI 2026-11-23 15:50:00 → MDW 2026-11-23 17:10:00.

2026-11-23 · one way · Axel-exclusive $206.25

• Southwest Airlines WN3207 / WN726: RSW 2026-11-23 10:05:00 → MDW 2026-11-23 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
  • WN3207: RSW 2026-11-23 10:05:00 → BUF 2026-11-23 13:00:00; layover at BUF: 60 minutes.
  • WN726: BUF 2026-11-23 14:00:00 → MDW 2026-11-23 14:50:00.

2026-11-23 · one way · Axel-exclusive $206.25

• Southwest Airlines WN4492 / WN2803: RSW 2026-11-23 07:10:00 → MDW 2026-11-23 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
  • WN4492: RSW 2026-11-23 07:10:00 → MCO 2026-11-23 08:05:00; layover at MCO: 125 minutes.
  • WN2803: MCO 2026-11-23 10:10:00 → MDW 2026-11-23 12:05:00.

2026-11-23 · one way · Axel-exclusive $206.25

• Southwest Airlines WN1254 / WN2988: RSW 2026-11-23 11:10:00 → MDW 2026-11-23 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
  • WN1254: RSW 2026-11-23 11:10:00 → CMH 2026-11-23 13:40:00; layover at CMH: 65 minutes.
  • WN2988: CMH 2026-11-23 14:45:00 → MDW 2026-11-23 15:00:00.

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 22, 2026 · Return options
• Nov 24, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

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