Houston (HOU) to Chicago (MDW) flights
Southwest Airlines flies nonstop from William P. Hobby Airport to Chicago Midway International Airport, with about 42 flights a week in July 2026. The 937-mile flight takes about 2h 21m gate to gate.
- Distance
- 937 mi · 1,508 km
- Flight time
- 2h 21m
- Airlines
- 1
- Seats filled
- 83%
Airlines flying HOU to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 42 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 248,924 | 2h 21m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
HOU to MDW flight schedule
11 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 5:00am and the last at 8:50pm. 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 1156Southwest Airlines | 5:00am | 7:25am | 12 | 75% |
| WN 149Southwest Airlines | 6:50am | 9:15am | 16 | 94% |
| WN 265Southwest Airlines | 7:20am | 9:50am | 24 | 67% |
| WN 256Southwest Airlines | 9:40am | 12:15pm | 12 | 83% |
| WN 398Southwest Airlines | 10:30am | 1:00pm | 4 | n/a |
| WN 1988Southwest Airlines | 11:55am | 2:20pm | 4 | n/a |
| WN 1964Southwest Airlines | 2:20pm | 4:40pm | 12 | 46% |
| WN 158Southwest Airlines | 3:50pm | 6:15pm | 12 | 58% |
| WN 1966Southwest Airlines | 5:45pm | 8:10pm | 24 | 42% |
| WN 2771Southwest Airlines | 7:55pm | 10:15pm | 16 | 69% |
| WN 2278Southwest Airlines | 8:50pm | 11:10pm | 12 | 67% |
Is HOU to MDW on time?
From September 2025 to August 2026, 71% of 1,843 flights arrived within 15 minutes of schedule and 1% were cancelled. Flights leaving around 6am were the most punctual (88%), those around 4pm the least (50%). Most delay time was caused by late-arriving aircraft (42%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,843 | 71% | 16 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 |
|---|---|---|---|
| 5am to 6am | 111 | 87% | |
| 6am to 7am | 199 | 88% | |
| 7am to 8am | 72 | 86% | |
| 8am to 9am | 133 | 82% | |
| 9am to 10am | 48 | 89% | |
| 10am to 11am | 37 | 92% | |
| 11am to 12pm | 135 | 80% | |
| 12pm to 1pm | 82 | 76% | |
| 1pm to 2pm | 51 | 50% | |
| 2pm to 3pm | 195 | 63% | |
| 3pm to 4pm | 95 | 53% | |
| 4pm to 5pm | 100 | 50% | |
| 6pm to 7pm | 152 | 59% | |
| 7pm to 8pm | 128 | 65% | |
| 8pm to 9pm | 158 | 65% | |
| 9pm to 10pm | 87 | 55% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 164 | 24,078 | |
| September 2025 | 162 | 21,717 | |
| October 2025 | 154 | 21,354 | |
| November 2025 | 137 | 17,784 | |
| December 2025 | 146 | 18,923 | |
| January 2026 | 128 | 15,631 | |
| February 2026 | 115 | 14,138 | |
| March 2026 | 154 | 21,316 | |
| April 2026 | 147 | 20,240 | |
| May 2026 | 150 | 22,252 | |
| June 2026 | 166 | 24,307 | |
| July 2026 | 186 | 27,184 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.