Fort Myers (RSW) to Chicago (MDW), Jan 14–21, 2027: from $315 round trip
Fort Myers (RSW) to Chicago (MDW), Jan 14–21, 2027: from $315 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $315 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 14–21, 2027, 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.
| Exact travel dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-14 → 2027-01-21 | Southwest Airlines | WN4492 + WN2803 / WN2737 + WN4149 | 07:10:00→12:05:00 5h 55m 1 stop via MCO · 11:30:00→17:45:00 5h 15m 1 stop via STL | Axel-exclusive $315.00 | 2026-10-29T01:07:18Z |
| 2027-01-14 → 2027-01-21 | Delta Air Lines | DL2277 + DL4688 / DL2417 + DL1124 | 08:00:00→13:01:00 6h 01m 1 stop via DTW · 13:02:00→18:54:00 4h 52m 1 stop via ATL | Axel-exclusive $390.00 | 2026-10-29T01:07:18Z |
| 2027-01-14 → 2027-01-21 | Southwest Airlines | WN3207 + WN726 / WN2737 + WN4149 | 10:05:00→14:50:00 5h 45m 1 stop via BUF · 11:30:00→17:45:00 5h 15m 1 stop via STL | Axel-exclusive $315.00 | 2026-10-29T01:07:18Z |
| 2027-01-14 → 2027-01-21 | Southwest Airlines | WN1254 + WN2988 / WN2737 + WN4149 | 11:10:00→15:00:00 4h 50m 1 stop via CMH · 11:30:00→17:45:00 5h 15m 1 stop via STL | Axel-exclusive $315.00 | 2026-10-29T01:07:18Z |
| 2027-01-14 → 2027-01-21 | Southwest Airlines | WN1388 + WN2062 / WN2737 + WN4149 | 10:35:00→16:15:00 6h 40m 1 stop via BNA · 11:30:00→17:45:00 5h 15m 1 stop via STL | Axel-exclusive $315.00 | 2026-10-29T01:07:18Z |
| 2027-01-14 → 2027-01-21 | Southwest Airlines | WN1676 / WN2737 + WN4149 | 18:10:00→20:10:00 3h 00m nonstop · 11:30:00→17:45:00 5h 15m 1 stop via STL | Axel-exclusive $327.50 | 2026-10-29T01:07:18Z |
Route overview: Fort Myers to Chicago (MDW) flight deals
2027-01-14 → 2027-01-21 · Axel-exclusive $315.00
- Southwest Airlines WN4492 / WN2803: RSW 2027-01-14 07:10:00 → MDW 2027-01-14 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
- WN4492: RSW 2027-01-14 07:10:00 → MCO 2027-01-14 08:05:00; layover at MCO: 125 minutes.
- WN2803: MCO 2027-01-14 10:10:00 → MDW 2027-01-14 12:05:00.
- Southwest Airlines WN2737 / WN4149: MDW 2027-01-21 11:30:00 → RSW 2027-01-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 100 minutes.
- WN4149: STL 2027-01-21 14:20:00 → RSW 2027-01-21 17:45:00.
2027-01-14 → 2027-01-21 · Axel-exclusive $390.00
- Delta Air Lines DL2277 / DL4688: RSW 2027-01-14 08:00:00 → MDW 2027-01-14 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
- DL2277: RSW 2027-01-14 08:00:00 → DTW 2027-01-14 10:54:00; layover at DTW: 110 minutes.
- DL4688: DTW 2027-01-14 12:44:00 → MDW 2027-01-14 13:01:00.
- Delta Air Lines DL2417 / DL1124: MDW 2027-01-21 13:02:00 → RSW 2027-01-21 18:54:00; 1 stop(s) via ATL; 292 minutes. Local airport times.
- DL2417: MDW 2027-01-21 13:02:00 → ATL 2027-01-21 16:01:00; layover at ATL: 76 minutes.
- DL1124: ATL 2027-01-21 17:17:00 → RSW 2027-01-21 18:54:00.
2027-01-14 → 2027-01-21 · Axel-exclusive $315.00
- Southwest Airlines WN3207 / WN726: RSW 2027-01-14 10:05:00 → MDW 2027-01-14 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
- WN3207: RSW 2027-01-14 10:05:00 → BUF 2027-01-14 13:00:00; layover at BUF: 60 minutes.
- WN726: BUF 2027-01-14 14:00:00 → MDW 2027-01-14 14:50:00.
- Southwest Airlines WN2737 / WN4149: MDW 2027-01-21 11:30:00 → RSW 2027-01-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 100 minutes.
- WN4149: STL 2027-01-21 14:20:00 → RSW 2027-01-21 17:45:00.
2027-01-14 → 2027-01-21 · Axel-exclusive $315.00
- Southwest Airlines WN1254 / WN2988: RSW 2027-01-14 11:10:00 → MDW 2027-01-14 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
- WN1254: RSW 2027-01-14 11:10:00 → CMH 2027-01-14 13:40:00; layover at CMH: 65 minutes.
- WN2988: CMH 2027-01-14 14:45:00 → MDW 2027-01-14 15:00:00.
- Southwest Airlines WN2737 / WN4149: MDW 2027-01-21 11:30:00 → RSW 2027-01-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 100 minutes.
- WN4149: STL 2027-01-21 14:20:00 → RSW 2027-01-21 17:45:00.
2027-01-14 → 2027-01-21 · Axel-exclusive $315.00
- Southwest Airlines WN1388 / WN2062: RSW 2027-01-14 10:35:00 → MDW 2027-01-14 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
- WN1388: RSW 2027-01-14 10:35:00 → BNA 2027-01-14 11:45:00; layover at BNA: 180 minutes.
- WN2062: BNA 2027-01-14 14:45:00 → MDW 2027-01-14 16:15:00.
- Southwest Airlines WN2737 / WN4149: MDW 2027-01-21 11:30:00 → RSW 2027-01-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 100 minutes.
- WN4149: STL 2027-01-21 14:20:00 → RSW 2027-01-21 17:45:00.
2027-01-14 → 2027-01-21 · Axel-exclusive $327.50
- Southwest Airlines WN1676: RSW 2027-01-14 18:10:00 → MDW 2027-01-14 20:10:00; nonstop; 180 minutes. Local airport times.
- Southwest Airlines WN2737 / WN4149: MDW 2027-01-21 11:30:00 → RSW 2027-01-21 17:45:00; 1 stop(s) via STL; 315 minutes. Local airport times.
- WN2737: MDW 2027-01-21 11:30:00 → STL 2027-01-21 12:40:00; layover at STL: 100 minutes.
- WN4149: STL 2027-01-21 14:20:00 → RSW 2027-01-21 17:45:00.
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.
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