Flights from Oakland (OAK) to Chicago (MDW)

Book low fares from Oakland to Chicago (Midway) with Southwest Airlines®. It’s easy to find the Oakland International Airport to Chicago Midway International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.

Explore your options and book your Oakland to Chicago (Midway) flight with Southwest today!

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Best Airline in the U.S. and North America & Best Economy and Low Cost Airline in North America.

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Low fare alert

Oakland, CA to Chicago (Midway), IL

departing on 12/03

one-way starting at*

$123
Book now

*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.

Check out Oakland to Chicago (Midway) flights and book yours now!

Middle seats open through November 30

Full exchange of fresh, outdoor air every 2-3 minutes while inflight

Face coverings required

Flight details

Average flight time: 4 hours 6 minutes

Departing from: Oakland International Airport (OAK)

Arriving at: Chicago Midway International Airport (MDW)

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Route information

2

Nonstop flightsper day

12

Daily flights

33

Weekly flights

9

Flightsbefore noon

2

Flightsbetween
12-6pm

View our interactive map

Based on DOT published scheduled average flights Monday-Friday between 10/9/2020 and 12/31/2020, as of 10/9/2020.

Travel tips

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Infancy policy

One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.

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Pet policy

Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.

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Unaccompanied minor

Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.

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Bags fly free®1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.

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The Southwest travel experience

At Southwest, we know it takes more than great deals on Chicago (Midway) airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Oakland to Chicago (Midway) the best it can be. Find out more about the Southwest® Experience before you book your Oakland International Airport to Chicago Midway International Airport flight.

Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. And when you search for your next flight to Chicago (Midway), you know you won’t be surprised at checkout. Low fares, no hidden fees. That’s our Transfarency® promise. And, as always, bags fly free. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Looking for tours, activities, and more hidden gems to add to your Chicago (Midway) adventure? Explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.

1First and second checked bags. Weight and size limits apply.

2Fare difference may apply.

Questions we hear the most

How long is the flight from Oakland to Chicago (Midway)?

The average flight time from Oakland to Chicago (Midway) is 4 hours 6 minutes.

How many Southwest flights from Oakland to Chicago (Midway) occur daily?

There are 12 flights daily from Oakland to Chicago (Midway) on Southwest Airlines.

Does Southwest fly nonstop from Oakland to Chicago (Midway)?

Southwest flies nonstop from Oakland to Chicago (Midway) 2 times daily.

What day is it cheapest to fly from Oakland to Chicago (Midway)?

To find the cheapest day and time to fly Oakland to Chicago (Midway) with Southwest, check out our Low Fare Calendar.

Can I rent a car at Chicago Midway International Airport?

You can rent a car at Chicago Midway International Airport—book yours with your flight.

Can I change my flight reservation for my flight from Oakland to Chicago (Midway)?

Yes! Flights from Oakland to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.

Where can I find the status of my flight from Oakland to Chicago (Midway)?

Check the status of your upcoming Southwest flight here.

Where can I find answers to other questions about flying from Oakland to Chicago (Midway) with Southwest?

Check out the Southwest Airlines® FAQs for answers about everything Southwest.