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.
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).
Cities with daily nonstop flights Monday through Friday to MDW
72†
Cities with daily nonstop flights Saturday through Sunday to MDW
73‡
*Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2025 and 3/31/2025. Note: route may not operate every day of the week.
†Nonstop flights based on DOT published scheduled average flights Monday through Friday between 3/1/2025 and 3/31/2025.
‡Nonstop flights based on DOT published scheduled average flights Saturday through Sunday between 3/1/2025 and 3/31/2025.
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