Nonstop flights from Chicago to Oakland
Southwest Airlines flies this route 1 to 2 times a day.
MDWChicago Midway International
1,840 mi · 13 flights a week
OAKOakland San Francisco Bay
When they leave
Chicago time10:15a8:35pFirst departure 10:15 AM, last 8:35 PM
One morning flight at 10:15 AM, then two in the evening, 8:25 PM to 8:35 PM.
Every flight
Earliest first
Schedules last checked Sep 19, 2026. Times are local.
Flying from Chicago to Oakland
Southwest Airlines is the only airline flying nonstop from Chicago to Oakland, 1 to 2 times a day on the Boeing 737 MAX 8.
There are 1 or 2 flights every day of the week. The first arrival in Oakland is at 12:40 PM and the last at 11:05 PM. The flight covers 1,840 miles.
Flying back, Oakland to Chicago has 11 nonstop flights a week.
Return flights
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Find the cheapest day to fly from Chicago to Oakland.
Schedules as of Oct 9, 2026.