San Antonio (SAT) to Chicago (MDW) flights
Southwest Airlines flies nonstop from San Antonio International Airport to Chicago Midway International Airport, with about 14 flights a week in July 2026. The 1,036-mile flight takes about 2h 31m gate to gate.
- Distance
- 1,036 mi · 1,667 km
- Flight time
- 2h 31m
- Airlines
- 1
- Seats filled
- 80%
Airlines flying SAT to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 14 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 87,205 | 2h 31m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
SAT to MDW flight schedule
5 flight numbers flew this route in August 2026. The first usually leaves at 5:00am and the last at 2:50pm. 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 586Southwest Airlines | 5:00am | 7:35am | 12 | 92% |
| WN 3790Southwest Airlines | 7:00am | 9:35am | 4 | n/a |
| WN 3946Southwest Airlines | 9:25am | 12:00pm | 8 | n/a |
| WN 245Southwest Airlines | 2:15pm | 4:50pm | 12 | 33% |
| WN 3503Southwest Airlines | 2:50pm | 5:25pm | 16 | 81% |
Is SAT to MDW on time?
From September 2025 to August 2026, 76% of 659 flights arrived within 15 minutes of schedule and 1.1% were cancelled. Flights leaving around 5am were the most punctual (92%), those around 3pm the least (49%). Most delay time was caused by late-arriving aircraft (48%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 659 | 76% | 12 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 |
|---|---|---|---|
| 5am to 6am | 47 | 92% | |
| 6am to 7am | 127 | 89% | |
| 9am to 10am | 116 | 87% | |
| 2pm to 3pm | 205 | 69% | |
| 3pm to 4pm | 106 | 49% | |
| 4pm to 5pm | 18 | 77% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 60 | 7,210 | |
| September 2025 | 56 | 6,840 | |
| October 2025 | 62 | 8,697 | |
| November 2025 | 54 | 6,763 | |
| December 2025 | 60 | 7,498 | |
| January 2026 | 36 | 4,324 | |
| February 2026 | 28 | 3,451 | |
| March 2026 | 56 | 7,835 | |
| April 2026 | 59 | 8,141 | |
| May 2026 | 63 | 8,568 | |
| June 2026 | 60 | 8,738 | |
| July 2026 | 61 | 9,140 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.