San Jose to Chicago (SJC–MDW) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
SJC–MDW is served by 3 airlines with nonstop service. Southwest Airlines leads the route. The flight covers 1,833 miles in approximately 4h 5m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 27 | 7M8, 7S7, B38M | 4h-4h10 | – | – | |
| BBQ BBQ | 0 | – | – | – | – | |
| TWY TWY | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from San Jose
| Metric | SJC→MDW | OAK→MDW | SFO→MDW |
|---|---|---|---|
| Distance from SJC | – | 29 mi | 30 mi |
| Nonstop airlines | 3 | 11 | 10 |
| Weekly flights | 28 | 25 | 28 |
| Flight time | 4h 5m | 3h 36m | 3h 45m |
| Departure OTP | 52% | – | – |
Travel Essentials
SJC: PDT · MDW: CDT
When it's 6:00 PM in San Jose, it's 8:00 PM in Chicago.
SJC–MDW Quick Facts
Frequently Asked Questions
Flights from SJC to MDW
Norman Y. Mineta San Jose International Airport (SJC) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 28 weekly departures, this is a heavily served route.
SJC to MDW Flight Duration and Schedule
Nonstop flight time from SJC to MDW is about 4 hours 5 minutes gate to gate. The route covers a distance of 1,833 miles (2,950 km). There are approximately 28 weekly flights outbound and 25 return, totaling 53 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Denver, Salt Lake City and Harry Reid. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Oakland (OAK), San Francisco (SFO) and Monterey (MRY).