San Diego (SAN) to Chicago (MDW) flights
Southwest Airlines flies nonstop from San Diego International Airport to Chicago Midway International Airport, with about 23 flights a week in July 2026. The 1,728-mile flight takes about 3h 49m gate to gate.
- Distance
- 1,728 mi · 2,781 km
- Flight time
- 3h 49m
- Airlines
- 1
- Seats filled
- 85%
Airlines flying SAN to MDW
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 23 | Boeing 737 MAX 8, Boeing 737-700 / MAX 7, Boeing 737-800 | 150,014 | 3h 49m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
SAN to MDW flight schedule
7 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 6:20am and the last at 10:40pm. 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 1184Southwest Airlines | 6:20am | 12:20pm | 4 | n/a |
| WN 770Southwest Airlines | 6:45am | 12:45pm | 16 | 56% |
| WN 3430Southwest Airlines | 6:55am | 12:55pm | 12 | 92% |
| WN 3137Southwest Airlines | 11:05am | 5:00pm | 12 | 0% |
| WN 4443Southwest Airlines | 11:10am | 5:05pm | 12 | 42% |
| WN 657Southwest Airlines | 5:50pm | 11:45pm | 12 | 17% |
| WN 3431Southwest Airlines | 10:40pm | 4:30am | 28 | 96% |
Is SAN to MDW on time?
From September 2025 to August 2026, 77% of 1,110 flights arrived within 15 minutes of schedule and 1.1% were cancelled. Flights leaving around 10pm were the most punctual (95%), those around 5pm the least (60%). Most delay time was caused by late-arriving aircraft (50%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,110 | 77% | 13 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 | 285 | 90% | |
| 7am to 8am | 50 | 84% | |
| 8am to 9am | 37 | 81% | |
| 10am to 11am | 106 | 78% | |
| 11am to 12pm | 100 | 61% | |
| 12pm to 1pm | 94 | 66% | |
| 1pm to 2pm | 27 | 68% | |
| 3pm to 4pm | 37 | 22% | |
| 4pm to 5pm | 30 | 69% | |
| 5pm to 6pm | 67 | 60% | |
| 6pm to 7pm | 65 | 63% | |
| 7pm to 8pm | 31 | 53% | |
| 10pm to 11pm | 180 | 95% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 88 | 13,067 | |
| September 2025 | 86 | 12,320 | |
| October 2025 | 89 | 12,461 | |
| November 2025 | 83 | 11,747 | |
| December 2025 | 91 | 12,586 | |
| January 2026 | 67 | 8,983 | |
| February 2026 | 66 | 8,788 | |
| March 2026 | 98 | 13,093 | |
| April 2026 | 103 | 13,895 | |
| May 2026 | 101 | 13,202 | |
| June 2026 | 101 | 15,059 | |
| July 2026 | 103 | 14,813 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.