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When the City in a Garden calls you away from Music City, Southwest Airlines® has you covered. Southwest® flies nonstop from Nashville International Airport to Chicago Midway International Airport. The Athens of the South will be easy to wave goodbye to when you discover how cheap flights are to Chicago (Midway). Your booking experience will be as straightforward as our pricing. Have flexible travel dates for your trip? Check out our Low Fare Calendar and discover our cheapest available flights within your selected dates. Find even more deals with Southwest Vacations® on trip add-ons like hotels, rental cars, and more.
Book your next flight from Nashville to Chicago (Midway) today!
Average Flight Time: 1 hour 25 minutes
Departing from: Nashville International Airport (BNA)
Arriving at: Chicago Midway International Airport (MDW)
All aboard the Orange Line—next stop, an urban adventure! When you arrive at Midway, you’ll be a 30-minute ‘L’ train ride from downtown Chicago (or as locals call it, the Loop). Shop the world famous Magnificent Mile, explore Millennium Park, visit the museum campus—there’s plenty to do downtown in the City by the Lake. Take in the breathtaking views of the iconic skyline, and consider going out on a limb to see it in even better detail. The Willis Tower (or Sears Tower, to diehard Chicagoans) features a series of enclosed ledges onto which brave souls can step, more than a thousand feet above the city streets below. Thrill seekers and lovers of great photo ops for social media, step right up!
Chicagoans are passionate about food, from street fare to Michelin-starred plates. There’s something for every palate in the City of the Big Shoulders, but there’s a good chance that visitors will have their hearts set on Chicago-style pizza. Contrary to what late-night talk show hosts and viral videos would have you believe, though, deep dish isn’t the only game in town; it isn’t even what natives would call truly Chicago style. For that, find yourself a thin-crust pie, cut tavern style. Hungry for more? Try a Chicago-style hotdog, “dragged through the garden”: mustard, relish, sport peppers, pickle, onions, tomatoes, and celery salt. Don’t even think about asking for ketchup—many hotdog joints have been known to kick folks out for daring to do so!
Scoring a great deal on a flight to Chicago (Midway) means you can focus on planning—and enjoying—the rest of your trip. What will you explore on your visit?
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.
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.
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.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
Making a memorable trip from Nashville to Chicago (Midway) is about more than a cheap flight. That’s why Southwest Crew Members work so hard to make sure that your time with us is as enjoyable as it is affordable. Learn more about what to expect from the Southwest Experience and book your next flight with us.
Flying to Chicago (Midway) with Southwest is as fun as it is straightforward; you can expect the same to be true of flying to any one of our dozens of other destinations. Low fares, no hidden fees—that’s Transfarency®. Stay up to date with the latest flight deals by enrolling in our Click 'N Save® emails. Looking for tours, activities, and more hidden gems? Check out Southwest Airlines® Experiences and earn Rapid Rewards® when you book.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.