Chicago to Oakland

MDWOAK

Fly from Chicago to Oakland starting at USD 140 with Southwest Airlines.Best fare available on Sep 18, 2026.Limited seats. Better plans. Book before it's gone.

Chicago to Oakland cheapest flights this week

18 Sept
Southwest Airlines
20:35MDW
01:10OAK
DirectUSD 140VIEW DEAL
19 Sept
Southwest Airlines
05:40MDW
12:10OAK
1 StopUSD 140VIEW DEAL
19 Sept
Southwest Airlines
10:05MDW
16:25OAK
DirectUSD 235VIEW DEAL
22 Sept
Southwest Airlines
10:15MDW
14:40OAK
DirectUSD 278VIEW DEAL
24 Sept
Frontier Airlines
12:54MDW
11:22OAK
2 StopUSD 266VIEW DEAL
12 Oct
Southwest Airlines
22:55MDW
09:40OAK
1 StopUSD 209VIEW DEAL
14 May
Southwest Airlines
10:15MDW
15:00OAK
DirectUSD 193VIEW DEAL

Chicago to Oakland monthly flight fare trend

Sep
from USD 140
Oct
from USD 209
Nov
No flights
Dec
No flights
Jan
No flights
Feb
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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