When Chicago winter is dragging you down, there’s nothing like a trip to Orlando to bring your spirits up! Actually, any time of the year is a great time for a flight from Chicago Midway International Airport to Orlando International Airport with Southwest Airlines®. Save on your trip to Orlando with cheap flights that will make you feel like you hit the airfare jackpot. Does your upcoming trip have flexible dates? If so, search for flights with our Low Fare Calendar and discover the lowest fares we’ve got. Make sure you explore Southwest Vacations® to find package deals on flights, hotels, rental cars, and more.
Explore Chicago (Midway) to Orlando flights and book yours today!
Chicago (Midway), IL to Orlando, FL
departing on 10/09
one-way starting at*$55
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 35 travel days available.
Average flight time: 2 hours 35 minutes
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Orlando International Airport (MCO)
Nonstop flightsper day
Other popular flights from ChicagoView our interactive map
†Based on DOT published scheduled average flights Monday-Friday between 8/4/2020 and 1/4/2021, as of 8/4/2020.
Whether you’re visiting Orlando for business, pleasure, or a mix of both, Orlando offers a unique experience for every traveler. Located in Central Florida, expect a welcome as warm as the weather when you meet the locals. But friendly Floridians aren’t the city’s only inhabitants. A robust range of wildlife thrives in the area’s humid subtropical climate, including alligators, snakes, and armadillos. Orlando’s other claim to fame: theme parks. With more than a dozen parks to choose from, Orlando is a hot spot for ride and game lovers across the world. And if you’re looking for a bite to eat, Orlando won’t disappoint. The city’s booming restaurant scene offers delicious cuisine and dining options that range from formal to casual.
Take a trip to see Orlando’s top sites. As far as attractions go, start by visiting the Kennedy Space Center. Just a hop, skip, and jump from Orlando, Florida’s space getaway is a stop worth making. Even if you don’t catch a rocket launch that day, learning about NASA’s revolutionary journey in space exploration is enough to take you to the stars. And once you’ve worked the left side of your brain, work the right side. The Orlando Museum of Art features several exceptional collections that will arrest your attention from the moment you walk in until the moment you leave.
Traveling is an excellent time to step outside of your comfort zone and embark on new adventures. At several locations around the city you can experience waterskiing, wakeboarding, wakeskating, and other watersports that never fail to deliver an adrenaline rush. If you would like to get in touch with nature, twist your way through mangrove tunnels on an Everglades airboat tour. The Everglades National Park is a one-of-a-kind experience that every person can enjoy, no matter what their age.
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 would like to help make your trip from Chicago (Midway) to Orlando unforgettable. We understand that a great trip from Chicago Midway International Airport to Orlando International Airport is built on more than just cheap flights. That’s why we offer services and perks, from booking to boarding, that make your travel experience smoother than ever. Discover more about the Southwest Experience before you book your Chicago (Midway) to Orlando flight.
Flying with Southwest is simple and fun, no matter which of our destinations you choose. And when you book your upcoming flight to Orlando you know you won’t be hassled by hidden fees. We offer low fares and, as always, bags fly free.1 That’s our Transfarency® promise. Enroll in our Click 'N Save® emails to stay in the loop about our latest flight deals. If you’re looking for tours, activities, and more hidden gems, check out Southwest Airlines Experiences and earn Rapid Rewards points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.