Southwest Airlines
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United States
Oakland International Airport
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United States
Midway International Airport
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Scan through all non-stop flights from Oakland, East Bay to Chicago. The full flight schedule below gives an overview of all non-stop flights from OAK to MDW, which includes the daily timetable of every operating airline for the upcoming 12 months.
Note: for airline-specific flight schedules, please scroll further down.
Currently, there is only one airline operating non-stop flights from Oakland, East Bay OAK to Chicago MDW, which is Southwest Airlines. This section gives an overview of the flight schedules and timetables of every airline with direct flights for this route.
Click an airline below to view their OAK MDW flight schedule.
Flights from OAK to MDW are operated 9 times a week, with an average of 1 flight per day. Departure times vary between 05:00 - 19:35. The earliest flight departs at 05:00, the last flight departs at 19:35. However, this depends on the date you are flying so please check with the full flight schedule above to see which departure times are available on your preferred date(s) of travel.
On this non-stop route, you can fly in Economy only.
The fastest direct flight from Oakland, East Bay to Chicago takes 4 hours and 10 minutes. The flight distance between Oakland, East Bay and Chicago is 1,838 miles (or 2,958 km).
There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (formerly Orchard Depot Fi (ORD).
There are 9 flights per week flying from Oakland, East Bay to Chicago (as of April 2024).
4 hours and 10 minutes is the average flight time from Oakland, East Bay to Chicago.
The distance from Oakland, East Bay to Chicago is 1,838 miles (2,958 kilometers).
Southwest Airlines is the only airline flying nonstop from Oakland, East Bay to Chicago.
There are no alliances flying direct from Oakland, East Bay to Chicago at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Oakland, East Bay to Chicago:
The earliest flight departs at 05:00 from Oakland, East Bay and arrives at 11:20 at Chicago.
The latest flight departs at 19:35 from Oakland, East Bay and arrives at 01:35 at Chicago.
1,838 miles (2,958 km) · 4h 10m
05:15
11:25
Southwest Airlines
WN 2901
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
06:00
12:10
Southwest Airlines
WN 2901
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
06:05
12:15
Southwest Airlines
WN 2901
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
08:10
14:15
Southwest Airlines
WN 2901
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
17:50
23:55
Southwest Airlines
WN 3332
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
18:25
00:30
Southwest Airlines
WN 594
Southwest Airlines
Boeing 737-700 (winglets)
Y
W
J
F
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