Fort Myers (RSW) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Southwest Florida International Airport to Chicago Midway International Airport, with about 19 flights a week in July 2026. The 1,105-mile flight takes about 2h 53m gate to gate.
- Distance
- 1,105 mi · 1,778 km
- Flight time
- 2h 53m
- Airlines
- 1
- Seats filled
- 83%
Airlines flying RSW to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 19 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 161,565 | 2h 53m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
RSW to MDW flight schedule
5 flight numbers flew this route in August 2026. The first usually leaves at 6:50am and the last at 5:40pm. Times are local and can change; check with the airline before you book.
| Flight | Departs | Arrives | Days flown in August 2026 | On time (12 months) |
|---|---|---|---|---|
| WN 2717Southwest Airlines | 6:50am | 8:40am | 12 | 100% |
| WN 4418Southwest Airlines | 7:10am | 8:55am | 16 | 94% |
| WN 3390Southwest Airlines | 11:55am | 1:45pm | 12 | 92% |
| WN 3394Southwest Airlines | 5:25pm | 7:15pm | 12 | 17% |
| WN 4872Southwest Airlines | 5:40pm | 7:30pm | 16 | 50% |
Is RSW to MDW on time?
From September 2025 to August 2026, 73% of 1,165 flights arrived within 15 minutes of schedule and 1.4% were cancelled. Flights leaving around 6am were the most punctual (94%), those around 5pm the least (41%). Most delay time was caused by late-arriving aircraft (56%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,165 | 73% | 17 min | 1.4% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 5am to 6am | 49 | 96% | |
| 6am to 7am | 162 | 94% | |
| 7am to 8am | 138 | 93% | |
| 9am to 10am | 29 | 97% | |
| 10am to 11am | 55 | 68% | |
| 11am to 12pm | 143 | 72% | |
| 12pm to 1pm | 67 | 89% | |
| 1pm to 2pm | 48 | 77% | |
| 2pm to 3pm | 42 | 54% | |
| 3pm to 4pm | 46 | 53% | |
| 4pm to 5pm | 86 | 73% | |
| 5pm to 6pm | 127 | 41% | |
| 6pm to 7pm | 37 | 44% | |
| 7pm to 8pm | 38 | 44% | |
| 8pm to 9pm | 55 | 56% | |
| 9pm to 10pm | 42 | 73% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 69 | 9,682 | |
| September 2025 | 69 | 9,180 | |
| October 2025 | 91 | 11,681 | |
| November 2025 | 86 | 12,011 | |
| December 2025 | 95 | 12,289 | |
| January 2026 | 100 | 13,662 | |
| February 2026 | 109 | 15,680 | |
| March 2026 | 154 | 23,180 | |
| April 2026 | 104 | 15,924 | |
| May 2026 | 91 | 12,650 | |
| June 2026 | 83 | 13,004 | |
| July 2026 | 84 | 12,622 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.