Orlando (MCO) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Orlando International Airport to Chicago Midway International Airport, with about 54 flights a week in July 2026. The 990-mile flight takes about 2h 48m gate to gate.
- Distance
- 990 mi · 1,593 km
- Flight time
- 2h 48m
- Airlines
- 1
- Seats filled
- 83%
Airlines flying MCO to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 54 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 345,254 | 2h 47m |
| Frontier AirlinesSeasonal or ended | n/a | Airbus A320neo, Airbus A321, Airbus A320-100/200 | 32,629 | 2h 54m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MCO to MDW flight schedule
13 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 6:55am and the last at 8:55pm. 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 359Southwest Airlines | 6:55am | 8:45am | 24 | 96% |
| WN 4895Southwest Airlines | 7:05am | 8:55am | 4 | n/a |
| WN 806Southwest Airlines | 8:15am | 10:00am | 12 | 100% |
| WN 2610Southwest Airlines | 10:00am | 11:45am | 16 | 69% |
| WN 290Southwest Airlines | 10:20am | 12:05pm | 12 | 82% |
| WN 4644Southwest Airlines | 1:00pm | 2:45pm | 12 | 64% |
| WN 4333Southwest Airlines | 1:50pm | 3:35pm | 12 | 58% |
| WN 106Southwest Airlines | 3:50pm | 5:40pm | 8 | n/a |
| WN 649Southwest Airlines | 4:10pm | 6:00pm | 12 | 36% |
| WN 679Southwest Airlines | 5:25pm | 7:15pm | 8 | n/a |
| WN 1429Southwest Airlines | 7:15pm | 9:00pm | 16 | 50% |
| WN 424Southwest Airlines | 7:45pm | 9:30pm | 10 | 50% |
| WN 693Southwest Airlines | 8:55pm | 10:40pm | 15 | 43% |
Is MCO to MDW on time?
From September 2025 to August 2026, 70% of 2,723 flights arrived within 15 minutes of schedule and 1.8% were cancelled. Flights leaving around 7am were the most punctual (92%), those around 5pm the least (53%). Most delay time was caused by late-arriving aircraft (41%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 2,532 | 70% | 19 min | 1.8% |
| Frontier Airlines | 191 | 75% | 22 min | 1% |
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 |
|---|---|---|---|
| 6am to 7am | 121 | 92% | |
| 7am to 8am | 292 | 92% | |
| 8am to 9am | 128 | 91% | |
| 9am to 10am | 144 | 81% | |
| 10am to 11am | 189 | 76% | |
| 11am to 12pm | 140 | 81% | |
| 12pm to 1pm | 158 | 74% | |
| 1pm to 2pm | 109 | 71% | |
| 2pm to 3pm | 143 | 71% | |
| 3pm to 4pm | 150 | 62% | |
| 4pm to 5pm | 193 | 63% | |
| 5pm to 6pm | 217 | 53% | |
| 6pm to 7pm | 219 | 59% | |
| 7pm to 8pm | 217 | 54% | |
| 8pm to 9pm | 129 | 47% | |
| 9pm to 10pm | 65 | 45% | |
| 10pm to 11pm | 100 | 65% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 223 | 31,498 | |
| September 2025 | 215 | 29,159 | |
| October 2025 | 245 | 33,841 | |
| November 2025 | 224 | 29,068 | |
| December 2025 | 239 | 29,343 | |
| January 2026 | 210 | 29,476 | |
| February 2026 | 204 | 29,077 | |
| March 2026 | 268 | 37,737 | |
| April 2026 | 214 | 31,211 | |
| May 2026 | 198 | 29,225 | |
| June 2026 | 226 | 33,503 | |
| July 2026 | 237 | 34,745 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.