Southwest Airlines
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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.
In Oakland, East Bay, the summers are known for being warm, long, and dry, with temperatures typically reaching about 30°C (86°F). The area’s breathtaking scenery complements the sun-filled lifestyle, making it a popular destination for visitors all year round who are looking for relaxation, fun by the water, and the beauty of the outdoors.
Oakland, East Bay is best explored from mid-spring to summer, specifically between April and September, as most rainfall occurs from October to February.
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 12 times a week, with an average of 2 flights per day. Departure times vary between 09:55 - 21:50. The earliest flight departs at 09:55, 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 35 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 12 flights per week flying from Chicago to Oakland, East Bay (as of April 2026).
4 hours and 35 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 09:55 from Chicago and arrives at 12:40 at Oakland, East Bay.
The latest flight departs at 21:50 from Chicago and arrives at 00:25 at Oakland, East Bay.
1,838 miles (2,958 km) · 4h 35m
09:55
12:40
Southwest Airlines
WN 2484
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
09:55
12:30
Southwest Airlines
WN 1743
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:00
12:35
Southwest Airlines
WN 192
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:50
Southwest Airlines
WN 2484
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
10:05
12:40
Southwest Airlines
WN 1743
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
17:55
20:30
Southwest Airlines
WN 1743
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
20:50
23:25
Southwest Airlines
WN 1743
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:30
00:10
Southwest Airlines
WN 1394
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:40
00:20
Southwest Airlines
WN 1394
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
21:50
00:25
Southwest Airlines
WN 1748
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
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