Chicago to Oakland (MDW–OAK) — Airlines, Schedules & Connections
No flights match your filters.
No nonstop flights on this route. connecting options below.
MDW–OAK is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,840 miles in approximately 4h 35m. Beyond nonstop, 102 hubs offer 1-stop connections.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| WN Southwest Airlines | 13 | 7M8, 7S7, B38M | 4h35 | – | – |
Weekly Schedule Pattern
Connection Landscape
Other ways to reach Oakland from Chicago
| Metric | MDW→OAK | RFD→OAK | MKE→OAK |
|---|---|---|---|
| Distance from MDW | – | 75 mi | 81 mi |
| Nonstop airlines | 1 | 1 | 1 |
| Weekly flights | 13 | – | – |
| Flight time | 4h 35m | 4h 10m | – |
| Departure OTP | 76% | – | – |
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 13 weekly departures, this is a regularly served route.
MDW to OAK Flight Duration and Schedule
Nonstop flight time from MDW to OAK ranges from 4 hours 35 minutes. The route covers a distance of 1,840 miles (2,961 km). There are approximately 13 weekly flights outbound and 12 return, totaling 25 flights per week in both directions.
Connecting Options and Alternatives
102 one-stop connections are available, with the fastest taking approximately 5 hours via YVR. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Chicago/Rockford (RFD), Milwaukee (MKE) and West Lafayette (LAF).