San Francisco (SFO) to Chicago (MDW) flights
Southwest Airlines flies nonstop from San Francisco International Airport to Chicago Midway International Airport, with about 14 flights a week in July 2026. The 1,855-mile flight takes about 4h 0m gate to gate.
- Distance
- 1,855 mi · 2,985 km
- Flight time
- 4h 0m
- Airlines
- 1
- Seats filled
- 85%
Airlines flying SFO 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 | 70,102 | 4h 0m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
SFO to MDW flight schedule
5 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 5:35am and the last at 11:40pm. 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 717Southwest Airlines | 5:35am | 11:40am | 12 | 100% |
| WN 4530Southwest Airlines | 8:00am | 2:00pm | 4 | n/a |
| WN 2499Southwest Airlines | 8:50am | 3:05pm | 4 | n/a |
| WN 957Southwest Airlines | 10:30am | 4:40pm | 8 | n/a |
| WN 3556Southwest Airlines | 11:40pm | 5:50am | 28 | 82% |
Is SFO to MDW on time?
From September 2025 to August 2026, 74% of 516 flights arrived within 15 minutes of schedule and 1.2% were cancelled. Flights leaving around 5am were the most punctual (90%), those around 10am the least (53%). Most delay time was caused by late-arriving aircraft (68%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 516 | 74% | 12 min | 1.2% |
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 | 157 | 90% | |
| 6am to 7am | 100 | 89% | |
| 7am to 8am | 13 | 85% | |
| 8am to 9am | 26 | 80% | |
| 10am to 11am | 36 | 53% | |
| 11pm to 12am | 180 | 55% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 30 | 5,038 | |
| September 2025 | 30 | 4,708 | |
| October 2025 | 31 | 4,273 | |
| November 2025 | 29 | 4,082 | |
| December 2025 | 31 | 4,402 | |
| January 2026 | 14 | 2,044 | |
| February 2026 | 19 | 2,158 | |
| March 2026 | 52 | 7,423 | |
| April 2026 | 58 | 7,991 | |
| May 2026 | 62 | 8,715 | |
| June 2026 | 60 | 9,722 | |
| July 2026 | 60 | 9,546 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.