Oakland to Chicago (OAK–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.
OAK–MDW is served by 2 airlines with nonstop service. Southwest Airlines leads the route. The flight covers 1,840 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 | 24 | 73H, 7M8, 7S7 | 4h-4h05 | – | – | |
| SGX SGX | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Oakland
| Metric | OAK→MDW | SFO→MDW | SJC→MDW |
|---|---|---|---|
| Distance from OAK | – | 11 mi | 29 mi |
| Nonstop airlines | 2 | 10 | 8 |
| Weekly flights | 25 | 28 | 28 |
| Flight time | 4h 5m | 3h 45m | 3h 30m |
| Departure OTP | 78% | – | – |
Travel Essentials
OAK: PDT · MDW: CDT
When it's 6:00 PM in Oakland, it's 8:00 PM in Chicago.
OAK–MDW Quick Facts
Frequently Asked Questions
Flights from OAK to MDW
San Francisco Bay Oakland International Airport (OAK) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 25 weekly departures, this is a well served route.
OAK to MDW Flight Duration and Schedule
Nonstop flight time from OAK to MDW is about 4 hours 5 minutes gate to gate. The route covers a distance of 1,840 miles (2,961 km). There are approximately 25 weekly flights outbound and 25 return, totaling 50 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Denver, Hollywood Burbank and Salt Lake City. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include San Francisco (SFO), San Jose (SJC) and Santa Rosa (STS).