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Whether you're heading home from visiting sunny Orlando or simply getting ready to explore the Windy City, Southwest Airlines® has the fares for you. Leave Florida behind—but not the magic! Chicago has world-class museums, shows, a rich history, and beautiful architecture to fill any visitor's itinerary. And from the Chicago Botanic Gardens to concerts at Ravinia, Chicagoland has a lot to offer just a train ride away from the city limits. Start planning your trip and book your Orlando International Airport to Chicago Midway International Airport flight today. Or, if your upcoming excursion has flexible dates, search for flights with our Low Fare Calendar and discover the lowest fares we've got. Don't forget to explore Southwest Vacations® to find package deals on flights, hotels, rental cars, and more.
Check out Orlando to Chicago (Midway) flights with Southwest® and book yours now!
Average Flight Time: 2 hours 45 minutes
Departing from: Orlando International Airport (MCO)
Arriving at: Chicago Midway International Airport (MDW)
Catch Broadway shows, rock concerts, dance performances, big games, and so much more in the City of Big Shoulders. With palatial downtown theaters to more intimate cabarets, you can catch almost any kind of show any day of the week. From Second City comedy to the Lyric Opera, Chicago is one of America's great hubs of culture and arts.
Choose from city tours about gangsters from Chicago's infamous past, spooky ghosts and hauntings, and architectural marvels. You can even walk in the footsteps of visitors to the 1893 World's Columbian Exposition, a landmark event in the city's history made even more famous by Erik Larson's Devil in the White City. Visit the Field Museum of Natural History, the only structure original to the Columbian Exposition still standing today, and learn about mummies, dinosaurs, and so much more. While you're at the Field Museum consider visiting the Adler Planetarium or the Shedd Aquarium, also located on Chicago's lakefront Museum Campus.
Whether you're traveling from Orlando for business or pleasure, you're sure to find sights and sounds to awe and delight. Flying up for a family visit? Check out Navy Pier! Got time after that business meeting wraps up? Head out to Michelin-rated restaurants, cozy bistros, gastropubs, trendsetting bars, or simply the local pizza joint. Prospective students of Chicagoland's many colleges and universities should make sure they take the time to get to know Chi-Town's neighborhoods. Long or short, your time in Chicago will be memorable.
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.
At Southwest, we know that a memorable trip from Orlando to Chicago is built with more than cheap flights from Orlando International Airport to Chicago Midway International Airport. That's why we offer services and perks, from booking to boarding, that make your travel experience the best it can be. Find out more about the Southwest Experience before you book your Orlando to Chicago (Midway) flight.
It's simple and fun to fly with Southwest, no matter which of our destinations you choose. And when you search for your next flight to Chicago (Midway), you can trust that you won't be hassled with hidden fees. That's our Transfarency® promise. Enroll in our Click 'N Save® emails and stay in the know about our latest flight deals. 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.