Southwest Airlines
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United States
Midway International Airport
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Oakland International Airport
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Scan through all non-stop flights from Chicago to Oakland, East Bay. The full flight schedule below gives an overview of all non-stop flights from MDW to OAK, 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 Chicago MDW to Oakland, East Bay OAK, 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 MDW OAK flight schedule.
Flights from MDW to OAK are operated 10 times a week, with an average of 1 flight per day. Departure times vary between 05:00 - 21:50. The earliest flight departs at 05:00, the last flight departs at 21:50. 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 Chicago to Oakland, East Bay takes 4 hours and 30 minutes. The flight distance between Chicago and Oakland, East Bay is 1,838 miles (or 2,958 km).
There is 1 airport in Oakland, East Bay: Oakland International Airport (OAK).
There are 10 flights per week flying from Chicago to Oakland, East Bay (as of March 2024).
4 hours and 30 minutes is the average flight time from Chicago to Oakland, East Bay.
The distance from Chicago to Oakland, East Bay is 1,838 miles (2,958 kilometers).
Southwest Airlines is the only airline flying nonstop from Chicago to Oakland, East Bay.
There are no alliances flying direct from Chicago to Oakland, East Bay at the moment.
You can fly non-stop in Economy only.
Aircraft types that fly from Chicago to Oakland, East Bay:
The earliest flight departs at 05:00 from Chicago and arrives at 07:45 at Oakland, East Bay.
The latest flight departs at 21:50 from Chicago and arrives at 00:20 at Oakland, East Bay.
1,838 miles (2,958 km) · 4h 30m
05:00
07:45
Southwest Airlines
WN 2607
Southwest Airlines
Boeing 737-700 (winglets)
Y
W
J
F
06:20
09:05
Southwest Airlines
WN 2607
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
07:35
10:15
Southwest Airlines
WN 2607
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:20
12:00
Southwest Airlines
WN 2607
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:30
20:10
Southwest Airlines
WN 383
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:50
20:30
Southwest Airlines
WN 383
Southwest Airlines
Boeing 737-700 (winglets)
Y
W
J
F
20:45
23:25
Southwest Airlines
WN 449
Southwest Airlines
Boeing 737-700 (winglets)
Y
W
J
F
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