Flights San Jose to Chicago SJC to MDW
Flights from San Jose (SJC) to Chicago (MDW): 1 airline operates 26 flight numbers on this route, about 7 flights a week, distance 2950 km / 1833 miles. The next departure is WN3854 (Southwest Airlines) on Sat, Nov 14 at 08:30 PST (16:30 GMT).
- 7 flights a week
- 1 airline
- 26 flight numbers
- 2950 km 1833 miles
- 3 h 45 min typical flight time
- 13/14 recent flights on time
Airlines and flight numbers count operating flights from a year ago to a year ahead; code-share numbers are not counted. On time means landed less than 15 minutes late.
San Jose to Chicago Flights
26 flight numbers from SJC to MDW, with the date each last flew. Local times: SJC PST, MDW CST.
| Flight | Airline | Last seen | Departure | Arrival |
|---|---|---|---|---|
 | Southwest Airlines | Nov 14, 2026 | 08:30 | 14:35 |
| | Southwest Airlines | Nov 13, 2026 | 23:00 | 05:00 |
| | Southwest Airlines | Nov 11, 2026 | 11:10 | 17:15 |
| | Southwest Airlines | Nov 11, 2026 | 06:00 | 12:10 |
| | Southwest Airlines | Oct 31, 2026 | 06:40 | 12:40 |
| | Southwest Airlines | Oct 30, 2026 | 23:00 | 05:00 |
| | Southwest Airlines | Oct 30, 2026 | 06:00 | 12:00 |
| | Southwest Airlines | Oct 28, 2026 | 11:15 | 17:15 |
| | Southwest Airlines | Oct 25, 2026 | 06:05 | 12:05 |
| | Southwest Airlines | Oct 24, 2026 | 09:05 | 15:05 |
| | Southwest Airlines | Sep 30, 2026 | 23:00 | 05:00 |
| | Southwest Airlines | Sep 30, 2026 | 09:55 | 16:00 |
| | Southwest Airlines | Sep 28, 2026 | 11:20 | 17:30 |
| | Southwest Airlines | Sep 27, 2026 | 06:10 | 12:20 |
| | Southwest Airlines | Aug 3, 2026 | 22:55 | 05:00 |
| | Southwest Airlines | Aug 3, 2026 | 10:05 | 16:10 |
| | Southwest Airlines | Aug 2, 2026 | 22:55 | 05:00 |
| | Southwest Airlines | Aug 1, 2026 | 10:30 | 16:35 |
| | Southwest Airlines | Jun 3, 2026 | 22:55 | 05:00 |
| | Southwest Airlines | Jun 3, 2026 | 10:50 | 16:55 |
| | Southwest Airlines | May 31, 2026 | 11:35 | 17:40 |
| | Southwest Airlines | Apr 6, 2026 | 22:55 | 05:00 |
| | Southwest Airlines | Apr 6, 2026 | 11:40 | 17:45 |
| | Southwest Airlines | Apr 5, 2026 | 11:55 | 17:55 |
| | Southwest Airlines | Mar 2, 2026 | 06:30 | 12:40 |
| | Southwest Airlines | Jan 5, 2026 | 06:30 | 12:40 |
Upcoming flights
Local times at the departure airport.| Flight | From | To | Scheduled Time | Departure | Status | Details |
|---|---|---|---|---|---|---|
| WN3854 | San Jose SJC | Chicago MDW | 08:30 | Scheduled | Track > |
Recent flights
Local times at the departure airport.On this route now
flights between SJC and MDW are in the air right now (live map).
Airlines flying SJC to MDW
SJC to MDW FAQ
- How long is the flight from San Jose to Chicago?
- About 3 h 45 min: that is the median flight time of the last 14 flights that landed; the timetable allows 4 h.
- Which airlines fly from San Jose to Chicago?
- Southwest Airlines has flights from San Jose (SJC) to Chicago (MDW) between a year ago and a year ahead. An airline listed may not fly the route every day.
- How many flights a week go from San Jose to Chicago?
- About 7 flights a week, counted over the two weeks before and after today. Only operating flights are counted, not code-share numbers.
- Are flights from San Jose to Chicago on time?
- 13 of the last 14 flights that landed arrived less than 15 minutes after their scheduled time.
- How far is San Jose from Chicago?
- 2950 km (1833 miles) in a straight line between San Jose International Airport and Chicago Midway International Airport.