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!
Orlando, FL to Chicago (Midway), IL
departing on 12/28
one-way starting at*$163
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 106 travel days available.
|Departing from||Orlando International Airport (MCO)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||2 hours 48 minutes|
|7‡||Nonstop flights per day Monday through Friday|
|8‡||Nonstop flights on Saturday|
|7‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2022 and 12/31/2022.
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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
At Southwest, we know it takes more than great deals on Chicago (Midway) 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 Orlando to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Orlando International Airport to Chicago Midway 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 Chicago (Midway), 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.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.