Explore Southwest Airlines® destination Chicago (Midway).

Midwest nice meets modern metropolis in the city that is always building, breaking, rebuilding.

Middle seats open through November 30

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

Face coverings required

TripAdvisor has rated us #1.

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

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Visit Chicago.

Since its settlement, Chicago (Midway) has been a major transportation hub. Standing in the Loop—what Chicagoans call their downtown—you certainly do get the feeling that you’re at the center of something thriving with nonstop motion. When visitors deplane at Chicago Midway International Airport, the movement begins immediately, whether the conveyance into big-city adventure is a rental car, a called car, or the city’s sprawling public transit system. The CTA’s Orange Line “L” train can speed you directly into the heart of the city—or you can work your way to wherever you’d like to go across Chi-Town.

The Second City has world-class offerings for everyone. Lovers of high-end shopping can visit the Magnificent Mile and browse high-fashion favorites. Art, history, and science buffs will love a day trip to the museum campus, though you could spend days exploring all of the Art Institute of Chicago alone—you may not make it to the Museum of Science and Industry or the Field Museum. The Adler Planetarium is also set among the museum campus and is worth a visit for space lovers. If the deep sea is more interesting to you than deep space, the Shedd Aquarium is a fantastic place to spend an afternoon with jellyfish and otters. Outdoor sightseeing opportunities abound around downtown Chicago, including Cloud Gate in Millennium Park and Buckingham Fountain in Grant Park.

The Magnificent Mile, the downtown parks, the lakefront, and the museum campus are all popular destinations for out-of-towners, and with good reason. But there’s so much more to Chicago than these popular spots and the Loop. Known as the City of Neighborhoods, there are 77 official community areas and somewhere around 200 neighborhoods (residents don’t always agree and neighborhoods are always evolving). Hop on the “L” or a bus and start exploring—head to one of the bungalow belts, explore historic communities built by vibrant immigrant and first-generation communities, and have yourself a hot dog dragged through the garden—covered in relish, onions, sport peppers, tomato slices, and a pickle spear.

The City in a Garden awaits. Book your next flight to Chicago (Midway) with Southwest® and start exploring. Southwest Airlines flies to Chicago Midway International Airport daily, so it’s always a good time to plan your next Chi-Town getaway. And when you book with Southwest, you can book with confidence, knowing that the process will be straightforward from flight selection to checkout. Of course, having a memorable trip is about more than finding a great deal on a flight. Learn more about the Southwest® Experience and book your upcoming flight to Chicago (Midway).

Got flexible travel plans?

Use our Low Fare Calendar to find the cheapest flights to Chicago (Midway) available inside your travel window.

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Things to do in Chicago.
Sightseeing opportunities
  • Skyscraper observation deck views
  • Riverboat architecture tours
  • Skyline helicopter tours
Popular parks
  • Grant Park
  • Millennium Park
  • The 606
Enriching outings
  • Adler Planetarium
  • Art Institute of Chicago
  • Shedd Aquarium

Other destinations in and beyond the Midwest.

Plan your next trip to one of the many cities served by Southwest.

 
Denver

See the world from a higher perspective. Let the Mile High City enamor you with its beautiful mix of urban and mountain style living.

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Dallas (Love Field)

Get ready to be wowed by the Big D! Dallas does everything big and they do it well—from blues to leading a herd of bronze steers.

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Houston (Hobby)

Explore this urban jewel of art and architecture steeped in diverse cultures and uniquely Texan history.

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Phoenix

See what life is like in the Valley of the Sun when you fly to Phoenix Sky Harbor International Airport.

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New York (LaGuardia)

Start planning your trip to the Big Apple by booking a flight into LaGuardia Airport.

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Austin

Austin is known for its quirky mix of attractions and activities to explore; see what makes this electrifying city wonderfully weird.

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Boston Logan

Pack your bags and head to Bean Town! This city of firsts blends innovation with plenty of history to explore during your stay.

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Los Angeles (LAX)

Experience the sparkle of Tinseltown—jet off to the West Coast for a visit to Los Angeles (LAX).

Read more
Check out our Route Tool for a full list of Southwest® destinations in every region.
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 Coronavirus Travel Information page for information about potential restrictions on air travel.

Plan your trip to Chicago (Midway).

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Plan a vacation.

Southwest Vacations® offers tons of vacation packages with amazing travel deals.

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Details about Chicago Midway International Airport.

Airport code:MDW

City:Chicago

State:Illinois

Terminals A&B

Gates A: 4a, 4b, 9, 11, 15-19, B: 1-3, 5, 7-12, 14-26

Airport-provided WiFi

60

Cities with nonstop daily service to MDW*

94

Cities with daily service to MDW*

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

Why fly Southwest?

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Bags fly free®1

Your bags fly free, because nothing should be left behind. So pack up without paying up with our two free checked bags.

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No change fees2

Think your plans may change? Don’t sweat it. We don’t charge you fees to change your mind2.

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Gate to gate WiFi3

Surf the web from origin to destination with gate-to-gate WiFi on your flight. Bring your device, and for $8 the Internet will make time fly by on all our flights.

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Fly in comfort

Southwest seats give you up to a 31-inch pitch, 17-inch width, and 2-inch recline, which all adds up to a more comfortable flight.

100% free entertainment.

Boredom doesn’t fly with us. So on your flight, watch a movie3 for free. Just one way we make getting to your destination as nice as being there. Well...almost.

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Your trip comes with low fares and no hidden fees thanks to Transfarency®.

Southwest is bringing our low fares and no hidden fees with us. We want to make your trip special, so we’re taking everything you love about Southwest and bringing it all to your travels. Get everything Transfarency has to offer on your next trip, only with Southwest.

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Join Rapid Rewards, our award-winning frequent flyer program4.

Southwest Rapid Rewards lets you use your points on any flight, any day, any time, which means you can turn your points into a reward flight. Sign up and see why we’ve been named the best rewards program four years in a row4. Points that actually reward you with getaways, that’s Southwest Rapid Rewards.

Sign up now

100% reward availability5.

You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.

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No blackout dates.

If there’s a seat available on a Southwest flight, you can use your points. It’s that easy. So no matter when you want to get away, you can use your points to get you there. As long as we have a spot available on a flight, you can book it with your Southwest Rapid Rewards points.

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Your points don’t expire.

No matter when you earn them, they’ll be there for you to redeem on your flight to anywhere you want to go.

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Rapid Rewards. Rapid redemption.

You can earn points on flights and on everyday purchases with our partners, which makes getting to our destinations easy. And our reward flights are based on our low fares, so the lower the fare, the fewer points you have to use. It’s almost like we want you to have the trip of a lifetime.

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

2Fare difference may apply.

3Download the Southwest® app to view movies and on-demand content. Inflight messaging only allows access to iMessage and WhatsApp. Apps must be downloaded before the flight. Internet access for $8 a day per device on WiFi-enabled aircraft. Price is subject to change. May not be available for the full duration of flight. Prohibits access to high-bandwidth applications and websites, including Netflix, HBO GO® and VoIP, along with certain obscene/offensive content.

42016-2019 Freddie Awards.

5As reported in the CarTrawler Reward Seat Availability Survey, May 16, 2019, and Switchfly Reward Seat Availability Surveys 2010 – 2019, at IdeaWorksCompany.com.