Cleveland (CLE) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Cleveland Hopkins International Airport to Chicago Midway International Airport, with about 26 flights a week in July 2026. The 307-mile flight takes about 1h 14m gate to gate.
- Distance
- 307 mi · 494 km
- Flight time
- 1h 14m
- Airlines
- 1
- Seats filled
- 67%
Airlines flying CLE to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 26 | Boeing 737-700 / MAX 7, Boeing 737 MAX 8, Boeing 737-800 | 116,498 | 1h 14m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
CLE to MDW flight schedule
9 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 8:50am and the last at 7:20pm. 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 1142Southwest Airlines | 8:50am | 9:00am | 28 | 71% |
| WN 1654Southwest Airlines | 12:50pm | 1:05pm | 8 | n/a |
| WN 1354Southwest Airlines | 1:45pm | 2:00pm | 4 | n/a |
| WN 2097Southwest Airlines | 1:50pm | 2:05pm | 12 | 83% |
| WN 4949Southwest Airlines | 4:35pm | 4:55pm | 8 | n/a |
| WN 1401Southwest Airlines | 5:25pm | 5:40pm | 10 | 20% |
| WN 491Southwest Airlines | 5:25pm | 5:40pm | 8 | n/a |
| WN 175Southwest Airlines | 7:15pm | 7:30pm | 20 | 50% |
| WN 1456Southwest Airlines | 7:20pm | 7:35pm | 4 | n/a |
Is CLE to MDW on time?
From September 2025 to August 2026, 81% of 1,115 flights arrived within 15 minutes of schedule and 1.1% were cancelled. Flights leaving around 6am were the most punctual (88%), those around 7pm the least (71%). Most delay time was caused by late-arriving aircraft (44%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,115 | 81% | 11 min | 1.1% |
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 | 165 | 88% | |
| 7am to 8am | 36 | 100% | |
| 8am to 9am | 136 | 81% | |
| 9am to 10am | 28 | 79% | |
| 12pm to 1pm | 73 | 82% | |
| 1pm to 2pm | 88 | 88% | |
| 2pm to 3pm | 43 | 84% | |
| 3pm to 4pm | 97 | 78% | |
| 4pm to 5pm | 112 | 83% | |
| 5pm to 6pm | 24 | 46% | |
| 6pm to 7pm | 44 | 93% | |
| 7pm to 8pm | 120 | 71% | |
| 8pm to 9pm | 107 | 71% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 110 | 13,612 | |
| September 2025 | 108 | 13,463 | |
| October 2025 | 94 | 10,787 | |
| November 2025 | 81 | 7,352 | |
| December 2025 | 89 | 8,583 | |
| January 2026 | 71 | 5,228 | |
| February 2026 | 71 | 5,948 | |
| March 2026 | 81 | 8,576 | |
| April 2026 | 87 | 8,677 | |
| May 2026 | 87 | 9,176 | |
| June 2026 | 107 | 12,292 | |
| July 2026 | 114 | 12,804 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.