San Jose (SJC) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Mineta San Jose International Airport to Chicago Midway International Airport, with about 14 flights a week in July 2026. The 1,838-mile flight takes about 3h 56m gate to gate.
- Distance
- 1,838 mi · 2,958 km
- Flight time
- 3h 56m
- Airlines
- 1
- Seats filled
- 85%
Airlines flying SJC 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 | 74,694 | 3h 56m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
SJC to MDW flight schedule
4 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 6:10am and the last at 11:00pm. 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 4847Southwest Airlines | 6:10am | 12:20pm | 4 | n/a |
| WN 208Southwest Airlines | 9:55am | 4:00pm | 12 | 83% |
| WN 1286Southwest Airlines | 11:20am | 5:30pm | 12 | 100% |
| WN 3607Southwest Airlines | 11:00pm | 5:00am | 28 | 75% |
Is SJC to MDW on time?
From September 2025 to August 2026, 85% of 526 flights arrived within 15 minutes of schedule and 0.2% were cancelled. Flights leaving around 6am were the most punctual (95%), those around 11am the least (68%). Most delay time was caused by late-arriving aircraft (44%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 526 | 85% | 6 min | 0.2% |
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 |
|---|---|---|---|
| 6am to 7am | 74 | 95% | |
| 7am to 8am | 20 | 90% | |
| 8am to 9am | 40 | 92% | |
| 9am to 10am | 12 | 92% | |
| 10am to 11am | 81 | 77% | |
| 11am to 12pm | 111 | 68% | |
| 10pm to 11pm | 152 | 93% | |
| 11pm to 12am | 28 | 75% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 54 | 8,122 | |
| September 2025 | 52 | 7,747 | |
| October 2025 | 32 | 5,010 | |
| November 2025 | 29 | 4,198 | |
| December 2025 | 31 | 4,540 | |
| January 2026 | 14 | 1,831 | |
| February 2026 | 19 | 2,403 | |
| March 2026 | 51 | 6,245 | |
| April 2026 | 56 | 7,352 | |
| May 2026 | 56 | 7,593 | |
| June 2026 | 58 | 9,730 | |
| July 2026 | 61 | 9,923 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.