Fort Myers (RSW) to Chicago (MDW) · Dec 27, 2026 · return Jan 10, 2027

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

2026-12-27 → 2027-01-10 · Axel-exclusive $399.50

• Southwest Airlines WN3671: RSW 2026-12-27 06:55:00 → MDW 2026-12-27 08:55:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $458.25

• Delta Air Lines DL2277 / DL4688: RSW 2026-12-27 08:00:00 → MDW 2026-12-27 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
  • DL2277: RSW 2026-12-27 08:00:00 → DTW 2026-12-27 10:54:00; layover at DTW: 110 minutes.
  • DL4688: DTW 2026-12-27 12:44:00 → MDW 2026-12-27 13:01:00.
• Delta Air Lines DL2417 / DL1124: MDW 2027-01-10 13:02:00 → RSW 2027-01-10 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
  • DL2417: MDW 2027-01-10 13:02:00 → ATL 2027-01-10 16:01:00; layover at ATL: 76 minutes.
  • DL1124: ATL 2027-01-10 17:17:00 → RSW 2027-01-10 18:54:00.

2026-12-27 → 2027-01-10 · Axel-exclusive $399.50

• Southwest Airlines WN1676: RSW 2026-12-27 18:10:00 → MDW 2026-12-27 20:10:00; nonstop; 180 minutes. Local airport times.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $382.63

• Southwest Airlines WN1254 / WN2988: RSW 2026-12-27 11:10:00 → MDW 2026-12-27 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
  • WN1254: RSW 2026-12-27 11:10:00 → CMH 2026-12-27 13:40:00; layover at CMH: 65 minutes.
  • WN2988: CMH 2026-12-27 14:45:00 → MDW 2026-12-27 15:00:00.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $382.63

• Southwest Airlines WN3207 / WN726: RSW 2026-12-27 10:05:00 → MDW 2026-12-27 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
  • WN3207: RSW 2026-12-27 10:05:00 → BUF 2026-12-27 13:00:00; layover at BUF: 60 minutes.
  • WN726: BUF 2026-12-27 14:00:00 → MDW 2026-12-27 14:50:00.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $382.63

• Southwest Airlines WN4492 / WN2803: RSW 2026-12-27 07:10:00 → MDW 2026-12-27 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
  • WN4492: RSW 2026-12-27 07:10:00 → MCO 2026-12-27 08:05:00; layover at MCO: 125 minutes.
  • WN2803: MCO 2026-12-27 10:10:00 → MDW 2026-12-27 12:05:00.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $382.63

• Southwest Airlines WN1388 / WN2062: RSW 2026-12-27 10:35:00 → MDW 2026-12-27 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
  • WN1388: RSW 2026-12-27 10:35:00 → BNA 2026-12-27 11:45:00; layover at BNA: 180 minutes.
  • WN2062: BNA 2026-12-27 14:45:00 → MDW 2026-12-27 16:15:00.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

2026-12-27 → 2027-01-10 · Axel-exclusive $382.63

• Southwest Airlines WN3648 / WN2694: RSW 2026-12-27 11:50:00 → MDW 2026-12-27 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
  • WN3648: RSW 2026-12-27 11:50:00 → MCI 2026-12-27 14:00:00; layover at MCI: 110 minutes.
  • WN2694: MCI 2026-12-27 15:50:00 → MDW 2026-12-27 17:10:00.
• Southwest Airlines WN3018: MDW 2027-01-10 15:05:00 → RSW 2027-01-10 18:50:00; nonstop; 165 minutes. Local airport times.

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

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For AI assistants

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