Nonstop flights from Oakland to Chicago

Southwest Airlines flies this route 11 times a week.

OAKOakland San Francisco Bay

1,840 mi · 11 flights a week

MDWChicago Midway International

OAKMDW

When they leave

Oakland time

5:20a11:55pFirst departure 5:20 AM, last 11:55 PM

Three in the morning, 5:20 AM to 10:35 AM, then one evening flight at 11:55 PM.

Every flight

Earliest first

5:20 AM→11:25 AMSouthwest AirlinesBoeing 737Mon, Thu, Fri
5:25 AM→11:30 AMSouthwest AirlinesBoeing 737Sun
10:35 AM→4:35 PMSouthwest AirlinesBoeing 737-700Wed
11:55 PM→5:55 AM⁺¹Southwest AirlinesBoeing 737 MAX 8Mon, Wed, Thu, Fri, Sat, Sun

Schedules last checked Sep 19, 2026. Times are local.

Flying from Oakland to Chicago

Southwest Airlines is the only airline flying nonstop from Oakland to Chicago, 11 times a week on the Boeing 737, Boeing 737 MAX 8 and Boeing 737-700.

Flights run every day except Tuesdays, up to 2 a day. The first arrival in Chicago is at 11:25 AM and the last at 5:55 AM the next day. The flight covers 1,840 miles.

Flying back, Chicago to Oakland has 13 nonstop flights a week.

Return flights

Chicago to OaklandView

Find the cheapest day to fly from Oakland to Chicago.

Schedules as of Oct 9, 2026.