Fort Myers (RSW) to Chicago (MDW) · Dec 29, 2026 · return Jan 5, 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.
| Exact travel dates | Airline | Flights | Total price | Price issued (UTC) |
|---|---|---|---|---|
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN1119 / WN3010 | Axel-exclusive $399.50 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Delta Air Lines | DL2277 + DL4688 / DL2417 + DL1124 | Axel-exclusive $458.25 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN3671 / WN3010 | Axel-exclusive $399.50 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN4492 + WN2803 / WN3010 | Axel-exclusive $382.63 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN3207 + WN726 / WN3010 | Axel-exclusive $382.63 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN3648 + WN2694 / WN3010 | Axel-exclusive $382.63 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN1388 + WN2062 / WN3010 | Axel-exclusive $382.63 | 2026-10-29T01:07:18Z |
| 2026-12-29 → 2027-01-05 | Southwest Airlines | WN1254 + WN2988 / WN3010 | Axel-exclusive $382.63 | 2026-10-29T01:07:18Z |
Route overview: Fort Myers to Chicago (MDW) flight deals
2026-12-29 → 2027-01-05 · Axel-exclusive $399.50
- Southwest Airlines WN1119: RSW 2026-12-29 14:55:00 → MDW 2026-12-29 17:00:00; nonstop; 185 minutes. Local airport times.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $458.25
- Delta Air Lines DL2277 / DL4688: RSW 2026-12-29 08:00:00 → MDW 2026-12-29 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
- DL2277: RSW 2026-12-29 08:00:00 → DTW 2026-12-29 10:54:00; layover at DTW: 110 minutes.
- DL4688: DTW 2026-12-29 12:44:00 → MDW 2026-12-29 13:01:00.
- Delta Air Lines DL2417 / DL1124: MDW 2027-01-05 13:02:00 → RSW 2027-01-05 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
- DL2417: MDW 2027-01-05 13:02:00 → ATL 2027-01-05 16:01:00; layover at ATL: 76 minutes.
- DL1124: ATL 2027-01-05 17:17:00 → RSW 2027-01-05 18:54:00.
2026-12-29 → 2027-01-05 · Axel-exclusive $399.50
- Southwest Airlines WN3671: RSW 2026-12-29 07:00:00 → MDW 2026-12-29 08:55:00; nonstop; 175 minutes. Local airport times.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $382.63
- Southwest Airlines WN4492 / WN2803: RSW 2026-12-29 07:10:00 → MDW 2026-12-29 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
- WN4492: RSW 2026-12-29 07:10:00 → MCO 2026-12-29 08:05:00; layover at MCO: 125 minutes.
- WN2803: MCO 2026-12-29 10:10:00 → MDW 2026-12-29 12:05:00.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $382.63
- Southwest Airlines WN3207 / WN726: RSW 2026-12-29 10:05:00 → MDW 2026-12-29 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
- WN3207: RSW 2026-12-29 10:05:00 → BUF 2026-12-29 13:00:00; layover at BUF: 60 minutes.
- WN726: BUF 2026-12-29 14:00:00 → MDW 2026-12-29 14:50:00.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $382.63
- Southwest Airlines WN3648 / WN2694: RSW 2026-12-29 11:50:00 → MDW 2026-12-29 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
- WN3648: RSW 2026-12-29 11:50:00 → MCI 2026-12-29 14:00:00; layover at MCI: 110 minutes.
- WN2694: MCI 2026-12-29 15:50:00 → MDW 2026-12-29 17:10:00.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $382.63
- Southwest Airlines WN1388 / WN2062: RSW 2026-12-29 10:35:00 → MDW 2026-12-29 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
- WN1388: RSW 2026-12-29 10:35:00 → BNA 2026-12-29 11:45:00; layover at BNA: 180 minutes.
- WN2062: BNA 2026-12-29 14:45:00 → MDW 2026-12-29 16:15:00.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
2026-12-29 → 2027-01-05 · Axel-exclusive $382.63
- Southwest Airlines WN1254 / WN2988: RSW 2026-12-29 11:10:00 → MDW 2026-12-29 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
- WN1254: RSW 2026-12-29 11:10:00 → CMH 2026-12-29 13:40:00; layover at CMH: 65 minutes.
- WN2988: CMH 2026-12-29 14:45:00 → MDW 2026-12-29 15:00:00.
- Southwest Airlines WN3010: MDW 2027-01-05 06:45:00 → RSW 2027-01-05 10:30:00; nonstop; 165 minutes. Local airport times.
Explore this route
- All dates for this route
- Dec 28, 2026 · Return options
- Dec 30, 2026 · Return options
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