Chicago (MDW) to San Diego (SAN) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to San Diego International Airport, with about 23 flights a week in July 2026. The 1,728-mile flight takes about 4h 14m gate to gate.
- Distance
- 1,728 mi · 2,781 km
- Flight time
- 4h 14m
- Airlines
- 1
- Seats filled
- 83%
Airlines flying MDW to SAN
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 23 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 152,217 | 4h 14m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MDW to SAN flight schedule
8 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 6:10am and the last at 8:45pm. 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 1887Southwest Airlines | 6:10am | 8:20am | 4 | n/a |
| WN 2814Southwest Airlines | 6:15am | 8:20am | 28 | 54% |
| WN 2815Southwest Airlines | 10:15am | 12:25pm | 12 | 48% |
| WN 363Southwest Airlines | 2:05pm | 4:10pm | 4 | n/a |
| WN 518Southwest Airlines | 2:50pm | 4:55pm | 12 | 33% |
| WN 2816Southwest Airlines | 3:05pm | 5:10pm | 8 | n/a |
| WN 3355Southwest Airlines | 8:25pm | 10:35pm | 4 | n/a |
| WN 4802Southwest Airlines | 8:45pm | 10:55pm | 24 | 52% |
Is MDW to SAN on time?
From September 2025 to August 2026, 69% of 1,110 flights arrived within 15 minutes of schedule and 1.2% were cancelled. Flights leaving around 6am were the most punctual (88%), those around 9pm the least (44%). Most delay time was caused by late-arriving aircraft (40%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 1,110 | 69% | 16 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 | 36 | 94% | |
| 6am to 7am | 127 | 88% | |
| 7am to 8am | 43 | 95% | |
| 8am to 9am | 120 | 78% | |
| 10am to 11am | 188 | 59% | |
| 11am to 12pm | 52 | 71% | |
| 1pm to 2pm | 50 | 80% | |
| 2pm to 3pm | 49 | 31% | |
| 3pm to 4pm | 51 | 66% | |
| 4pm to 5pm | 31 | 58% | |
| 5pm to 6pm | 59 | 62% | |
| 7pm to 8pm | 52 | 80% | |
| 8pm to 9pm | 157 | 67% | |
| 9pm to 10pm | 59 | 44% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 86 | 12,485 | |
| September 2025 | 85 | 11,964 | |
| October 2025 | 88 | 13,285 | |
| November 2025 | 84 | 11,651 | |
| December 2025 | 91 | 12,675 | |
| January 2026 | 67 | 8,837 | |
| February 2026 | 66 | 8,900 | |
| March 2026 | 99 | 13,777 | |
| April 2026 | 103 | 13,379 | |
| May 2026 | 104 | 13,738 | |
| June 2026 | 102 | 15,573 | |
| July 2026 | 104 | 15,953 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.