Direct flights from Chicago to Oakland, East Bay

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

Chicago

United States

United States

MDW

Midway International Airport

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Oakland, East Bay

United States

United States

OAK

Oakland 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 25 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
  • Boeing 737-800 (winglets)

Chicago to Oakland, East Bay Flight Schedule

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.

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Airlines flying from Chicago to Oakland, East Bay

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

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.

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

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Chicago to Oakland, East Bay Flights

Flights from MDW to OAK are operated 10 times a week, with an average of 1 flight per day. Departure times vary between 05:20 - 22:45. The earliest flight departs at 05:20, the last flight departs at 22:45. 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 25 minutes. The flight distance between Chicago and Oakland, East Bay is 1,838 miles (or 2,958 km).

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Frequently asked questions - FAQ

How many airports are there in Oakland, East Bay?

There is 1 airport in Oakland, East Bay: Oakland International Airport (OAK).

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

There are 10 flights per week flying from Chicago to Oakland, East Bay (as of January 2023).

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

4 hours and 25 minutes is the average flight time from Chicago to Oakland, East Bay.

How far is Oakland, East Bay from Chicago?

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

What airlines fly nonstop from MDW airport to OAK airport?

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

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

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

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

You can fly non-stop in Economy only.

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

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

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

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

The earliest flight departs at 05:20 from Chicago and arrives at 08:00 at Oakland, East Bay.

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

The latest flight departs at 22:45 from Chicago and arrives at 01:10 at Oakland, East Bay.

Non-stop flights from MDW to OAK

1,838 miles (2,958 km)  ·  4h 25m

Round trip
1 passenger
Economy
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Return schedule
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  • Depart
  • Arrive
  • Airline
  • Flight no
  • Aircraft
  • Classes
  • 09:05

  • 11:55

  • Southwest Airlines

    Southwest Airlines

  • WN 1100

  • Southwest Airlines

  • Boeing 737-700 (winglets)

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    F

  • 09:55

  • 12:40

  • Southwest Airlines

    Southwest Airlines

  • WN 2063

  • Southwest Airlines

  • Boeing 737 MAX 8

  • Y

    W

    J

    F

  • 21:35

  • 00:20

  • Southwest Airlines

    Southwest Airlines

  • WN 2859

  • Southwest Airlines

  • Boeing 737-700 (winglets)

  • Y

    W

    J

    F

  • 21:35

  • 00:20

  • Southwest Airlines

    Southwest Airlines

  • WN 2859

  • Southwest Airlines

  • Boeing 737 MAX 8

  • Y

    W

    J

    F

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