Fly into Chicagoland area airports with Southwest Airlines®.

Q: Can I rent a car at Chicagoland area airports?

Yes, you can rent a car at Chicagoland area airports— book yours with your flight .

Q: Can I change my flight reservation for my flight to Chicago?

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

Q: Where can I find answers to other questions about traveling to Chicago with Southwest?

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

Whether you’re headed to the Back of the Yards or the Gold Coast, Southwest® flies into both airports in Chicagoland. See which Chicago airport is the most convenient for your Windy City adventure.

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Enjoy all the benefits of Southwest Heart and Hospitality.

Free movies/TV¹ and $8 WiFi²

Boredom doesn’t fly with us. So on your flight, watch a blockbuster or catch up on your favorite shows for free.

Two bags fly free³

Your bags fly free, because no bag should be left behind. So pack up without paying up with our two free checked bags.

No change⁴ or cancel fees⁵

We understand plans change. If you’d like to change a flight itinerary, you’ll just pay for any fare difference.

Visit the Chicagoland area.

Southwest flies to both airports in the City of the Big Shoulders, which means you have double the options for finding low fares and convenient flight times for your next trip to the Windy City. Hop on the Blue Line after landing on the Northwest Side of the city or catch the Orange Line when you deplane on the South Side—whatever you do, don’t miss out on everything the Second City has to offer.

Where you can land in the Chicago area.

Wanna see Chicago? Choose where you’ll land when you wing your way to the city by the lake.

Chicago (Midway)

The hustle and bustle of the City of the Big Shoulders awaits. Enjoy a world class city filled with Midwest nice people—start your Chicagoland adventure.

Chicago (O'Hare)

See why the Second City is second to none when you start your adventure in Chicago, a metropolis steeped in rich history, culture, food, and more.

Check out our Route Tool for a full list of Southwest® destinations in every region.

Got flexible travel plans?

Use our Low Fare Calendar to find the lowest fares on flights into Chicagoland area airports available inside your travel window.

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Travel Advisory

During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.

Questions we hear the most

Southwest flies to Chicago Midway International Airport and Chicago O'Hare International Airport.

Yes, you can rent a car at Chicagoland area airports—book yours with your flight.

The Chicago Transit Authority (CTA) operates and extensive network of train and bus lines, and visitors who wish to venture outside the city can take advantage of the Metra train service.

Chicago has four distinct seasons, including hot, humid summers and cold, snowy winters—pack appropriately!

Millennium Park, the Willis Tower, the Museum Campus, and Restaurant Row.

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

Check the status of your upcoming Southwest flight to Chicago.

To view up-to-date information regarding travel restrictions, visit our COVID-19 Travel Information center.

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

¹Available only on WiFi-enabled aircraft. Limited-time offer. Where available.

²Internet access for $8 a day per device on WiFi-enabled aircraft. Price is subject to change. May not be available full duration of flight. In order to provide a top-notch WiFi experience, we prohibit access to certain high-bandwidth applications and websites, including Netflix, HBO GO® and VoIP. We also prohibit access to certain obscene or offensive content.

³First and second checked bags. Size and weight limits apply.

⁴Fare difference may apply.

⁵Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.

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