Chicago to Oakland
MDWOAK
Fly from Chicago to Oakland starting at USD 149 with Southwest Airlines.
Best fare available on Aug 6, 2026.
Limited seats. Better plans. Book before it's gone.
Chicago to Oakland cheapest flights this week
Chicago to Oakland monthly flight fare trend
Aug
from USD 149
Sep
No flights
Oct
No flights
Nov
No flights
Dec
No flights
Jan
No flights
Airport Details
Origin
Chicago
Chicago Midway International Airport (MDW)
Chicago, MDW
Zone
Chicago
Elev
620 ft
Destination
Oakland
San Francisco Bay Oakland International Airport (OAK)
Oakland, OAK
Zone
Los Angeles
Elev
9 ft
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