Direct flights from Oakland, East Bay to Chicago

Did you mean flights from Chicago to Oakland, East Bay?

Oakland, East Bay

United States

United States

OAK

Oakland International Airport

Switch direction

Chicago

United States

United States

MDW

Midway International Airport

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Flight schedule
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Click to show full flight schedule

Distance
1,838 miles  ·  (2,958 km)
Flight time
4 hours and 5 minutes
Airlines
  • Southwest Airlines
Alliances
  • OneWorld
  • SkyTeam
  • Star Alliance
Classes
  • Economy
  • Premium Economy
  • Business Class
  • First Class
Aircrafts
  • Boeing 737 MAX 8
  • Boeing 737-700 (winglets)
  • Boeing 737-800 (winglets)

Oakland, East Bay to Chicago Flight Schedule

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.

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Airlines flying from Oakland, East Bay to Chicago

Airline-specific flight schedules from Oakland, East Bay to Chicago

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.

Southwest Airlines
Southwest Airlines flight schedulefrom Oakland, East Bay to Chicago

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Oakland, East Bay to Chicago Flights

Flights from OAK to MDW are operated 7 times a week, with an average of 1 flight per day. Departure times vary between 05:15 - 18:10. The earliest flight departs at 05:15, the last flight departs at 18:10. 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 5 minutes. The flight distance between Oakland, East Bay and Chicago is 1,838 miles (or 2,958 km).

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Frequently asked questions - FAQ

How many airports are there in Chicago?

There are 2 airports in Chicago: Midway International Airport (MDW) and O'Hare International Airport (formerly Orchard Depot Fi (ORD).

How many flights per week are there from OAK to MDW?

There are 7 flights per week flying from Oakland, East Bay to Chicago (as of September 2021).

How long does it take to fly from Oakland, East Bay to Chicago?

4 hours and 5 minutes is the average flight time from Oakland, East Bay to Chicago.

How far is Chicago from Oakland, East Bay?

The distance from Oakland, East Bay to Chicago is 1,838 miles (2,958 kilometers).

What airlines fly nonstop from OAK airport to MDW airport?

Southwest Airlines is the only airline flying nonstop from Oakland, East Bay to Chicago.

What alliances have direct flights from Oakland, East Bay to Chicago?

There are no alliances flying direct from Oakland, East Bay to Chicago at the moment.

What classes are available from Oakland, East Bay to Chicago?

You can fly non-stop in Economy only.

What aircraft types fly from Oakland, East Bay to Chicago?

Aircraft types that fly from Oakland, East Bay to Chicago:

  • Boeing 737 MAX 8
  • Boeing 737-700 (winglets)
  • Boeing 737-800 (winglets)

What is the earliest flight departing from Oakland, East Bay to Chicago?

The earliest flight departs at 05:15 from Oakland, East Bay and arrives at 11:25 at Chicago.

What is the latest flight available from Oakland, East Bay to Chicago?

The latest flight departs at 18:10 from Oakland, East Bay and arrives at 00:15 at Chicago.

Non-stop flights from OAK to MDW

1,838 miles (2,958 km)  ·  4h 5m

Round trip
1 passenger
Economy
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Return schedule
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  • Depart
  • Arrive
  • Airline
  • Flight no
  • Aircraft
  • Classes
  • 05:25

  • 11:30

  • Southwest Airlines

    Southwest Airlines

  • WN 5043

  • Southwest Airlines

  • Boeing 737 MAX 8

  • Y

    W

    J

    F

  • 05:35

  • 11:40

  • Southwest Airlines

    Southwest Airlines

  • WN 980

  • Southwest Airlines

  • Boeing 737 MAX 8

  • Y

    W

    J

    F

  • 06:15

  • 12:25

  • Southwest Airlines

    Southwest Airlines

  • WN 2976

  • Southwest Airlines

  • Boeing 737-800 (winglets)

  • Y

    W

    J

    F

  • 06:50

  • 12:55

  • Southwest Airlines

    Southwest Airlines

  • WN 5964

  • Southwest Airlines

  • Boeing 737-800 (winglets)

  • Y

    W

    J

    F

  • 10:00

  • 16:05

  • Southwest Airlines

    Southwest Airlines

  • WN 2314

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

  • 11:05

  • 17:10

  • Southwest Airlines

    Southwest Airlines

  • WN 5870

  • Southwest Airlines

  • Boeing 737 MAX 8

  • Y

    W

    J

    F

  • 11:20

  • 17:25

  • Southwest Airlines

    Southwest Airlines

  • WN 3437

  • Southwest Airlines

  • Boeing 737-800 (winglets)

  • Y

    W

    J

    F

  • 12:55

  • 19:00

  • Southwest Airlines

    Southwest Airlines

  • WN 3852

  • Southwest Airlines

  • Boeing 737-800 (winglets)

  • Y

    W

    J

    F

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