Fly into Chicagoland area airports with Southwest Airlines®.

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

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?

Visit the Southwest Airlines ® Help Center for helpful information and answers to frequently asked questions.

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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When you fly Southwest

Two bags fly free®¹

No change² and no cancel fees³

Flight credits don't expire⁴

Free entertainment^5,6 and $8 Internet⁷

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.

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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Questions we hear the most

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

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.

Visit the Southwest Airlines® Help Center for helpful information and answers to frequently asked questions.

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

²Fare difference may apply.

³Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.

⁴Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.

⁵Where available. Available only on WiFi-enabled aircraft. Limited-time offer.

⁶Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.

⁷Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.

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