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 low fares on 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 10/23
one-way starting at*$99
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 16 travel days available.
|Departing from||Chicago Midway International Airport (MDW)|
|Arriving at||Orlando International Airport (MCO)|
|Average flight time||2 hours 33 minutes|
|4‡||Nonstop flights per day Monday through Friday|
|7‡||Nonstop flights on Saturday|
|7‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2023 and 9/30/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2023 and 9/30/2023.
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.
When you arrive at Orlando International Airport you're just six miles outside of downtown Orlando. Set the course for fun!
At Southwest, we know it takes more than great deals on Orlando airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Orlando the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Orlando International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Orlando, know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
6Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.