Fort Myers (RSW) to Chicago (MDW) · Dec 2, 2026 · one way

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

2026-12-02 · one way · Axel-exclusive $180.00

• Southwest Airlines WN2106: RSW 2026-12-02 13:05:00 → MDW 2026-12-02 15:00:00; nonstop; 175 minutes. Local airport times.

2026-12-02 · one way · Axel-exclusive $205.00

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

2026-12-02 · one way · Axel-exclusive $180.00

• Southwest Airlines WN3671: RSW 2026-12-02 07:00:00 → MDW 2026-12-02 08:55:00; nonstop; 175 minutes. Local airport times.

2026-12-02 · one way · Axel-exclusive $165.00

• Southwest Airlines WN1388 / WN2062: RSW 2026-12-02 10:35:00 → MDW 2026-12-02 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-12-02 10:35:00 → BNA 2026-12-02 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-12-02 14:45:00 → MDW 2026-12-02 16:15:00.

2026-12-02 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3648 / WN2694: RSW 2026-12-02 11:50:00 → MDW 2026-12-02 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
  • WN3648: RSW 2026-12-02 11:50:00 → MCI 2026-12-02 14:00:00; layover at MCI: 110 minutes.
  • WN2694: MCI 2026-12-02 15:50:00 → MDW 2026-12-02 17:10:00.

2026-12-02 · one way · Axel-exclusive $165.00

• Southwest Airlines WN3207 / WN726: RSW 2026-12-02 10:05:00 → MDW 2026-12-02 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
  • WN3207: RSW 2026-12-02 10:05:00 → BUF 2026-12-02 13:00:00; layover at BUF: 60 minutes.
  • WN726: BUF 2026-12-02 14:00:00 → MDW 2026-12-02 14:50:00.

2026-12-02 · one way · Axel-exclusive $165.00

• Southwest Airlines WN1254 / WN2988: RSW 2026-12-02 11:10:00 → MDW 2026-12-02 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
  • WN1254: RSW 2026-12-02 11:10:00 → CMH 2026-12-02 13:40:00; layover at CMH: 65 minutes.
  • WN2988: CMH 2026-12-02 14:45:00 → MDW 2026-12-02 15:00:00.

2026-12-02 · one way · Axel-exclusive $165.00

• Southwest Airlines WN4492 / WN2803: RSW 2026-12-02 07:10:00 → MDW 2026-12-02 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
  • WN4492: RSW 2026-12-02 07:10:00 → MCO 2026-12-02 08:05:00; layover at MCO: 125 minutes.
  • WN2803: MCO 2026-12-02 10:10:00 → MDW 2026-12-02 12:05:00.

Explore this route

• All dates for this route
• Dec 1, 2026 · Return options
• Dec 3, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Fort Myers (RSW) to Chicago (MDW) · Dec 2, 2026 · one way: 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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