Chicago to Oakland (MDW–OAK) — 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.
MDW–OAK is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,840 miles in approximately 4h 30m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 14 | 738, 7M8, B38M | 4h30-4h42 | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Oakland from Chicago
| Metric | MDW→OAK | ORD→OAK | RFD→OAK |
|---|---|---|---|
| Distance from MDW | – | 15 mi | 75 mi |
| Nonstop airlines | 1 | 1 | 1 |
| Weekly flights | 14 | 1 | – |
| Flight time | 4h 30m | 4h | 4h 10m |
| Departure OTP | 40% | – | – |
Travel Essentials
MDW: CDT · OAK: PDT
When it's 6:00 PM in Chicago, it's 4:00 PM in Oakland.
MDW–OAK Quick Facts
Frequently Asked Questions
Flights from MDW to OAK
Chicago Midway International Airport (MDW) and San Francisco Bay Oakland International Airport (OAK) are connected by nonstop service from Southwest Airlines. With 14 weekly departures, this is a well served route.
MDW to OAK Flight Duration and Schedule
Nonstop flight time from MDW to OAK is about 4 hours 30 minutes gate to gate. The route covers a distance of 1,840 miles (2,961 km). There are approximately 14 weekly flights outbound and 13 return, totaling 27 flights per week in both directions.
Connecting Options and Alternatives
1-stop connecting options are also available, commonly via Denver, Ontario and Harry Reid. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago (ORD), Chicago/Rockford (RFD) and Milwaukee (MKE).