Southwest Airlines
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United States
Oakland International Airport
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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.
Known for its continental climate, Chicago features hot, humid summers with temperatures above 30°C (86°F) and cold, snowy winters that often drop below 0°C (32°F). This striking seasonal contrast offers travelers a variety of activities, from summer hiking to winter sports, ensuring year-round appeal.
The best time to visit Chicago is from March to November, covering spring, summer, and fall. While summer can be hot, it also sees slightly more rainfall than other seasons.
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 12 times a week, with an average of 2 flights per day. Departure times vary between 05:05 - 23:55. The earliest flight departs at 05:05, the last flight departs at 23:55. 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. 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 (ORD).
There are 12 flights per week flying from Oakland, East Bay to Chicago (as of April 2026).
4 hours 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 05:05 from Oakland, East Bay and arrives at 11:10 at Chicago.
The latest flight departs at 23:55 from Oakland, East Bay and arrives at 05:55 at Chicago.
1,838 miles (2,958 km) · 4h
05:40
11:40
Southwest Airlines
WN 1150
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:45
11:45
Southwest Airlines
WN 1150
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:50
11:55
Southwest Airlines
WN 3551
Southwest Airlines
Boeing 757
Y
W
J
F
05:50
11:55
Southwest Airlines
WN 3551
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
05:55
12:00
Southwest Airlines
WN 3551
Southwest Airlines
Boeing 737 MAX 8
Y
W
J
F
23:55
05:55
Southwest Airlines
WN 4069
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
23:55
06:00
Southwest Airlines
WN 3552
Southwest Airlines
Boeing 737-800 (winglets)
Y
W
J
F
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