Looking for a fun-in-the-sun getaway from Chicago? Southwest Airlines is ready to get you on your way to the Sunshine State. Southwest has flights from Chicago O’Hare International Airport to Orlando International Airport with low prices that might surprise you. If you have a wide travel window, explore our Low Fare Calendar to find the lowest available fares inside your travel dates. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
Start planning your next getaway to the Sunshine State—see everything O-Town has to offer!
Chicago (O'Hare), IL to Orlando, FL
departing on 1/4
one-way starting at*$107
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 15 travel days available.
|Departing from||Chicago O'Hare International Airport (ORD)|
|Arriving at||Orlando International Airport (MCO)|
|Average flight time||2 hours 40 minutes|
|2‡||Nonstop flights per day Monday through Friday|
|2‡||Nonstop flights on Saturday|
|2‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2023 and 12/31/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 12/1/2023 and 12/31/2023.
Located in the middle of Florida, Orlando features picturesque wetlands, consisting of many lakes and freshwater swamps that beg to be explored. Although the city is known for its theme parks, take a closer look to find there’s a variety of activities no matter what brings you to the area.
Check out one of Florida’s hidden gems at Bok Tower Gardens, about one hour by car outside of downtown Orlando. The 250-acre garden features a Mediterranean-style 20-room winter home that dates back to the 1930s. Be sure to visit in the afternoon for the ringing of the bells. You can tap into your inner beatnik with a visit to the Jack Kerouac House, his home when he published one of his most famous books.
If you’re looking to get active, rent a bike and head over to Kissimmee Lakefront Park or one of Orlando’s over 30 riding trails. You might even get a peek of some of the local wildlife. Prefer to tee up on the links? Orlando has some of the top courses in the country that will challenge golfers of any skill level. And if you’re into birding, Orlando can’t be missed. Orlando Wetlands Park features over 220 bird species including ospreys, short-tailed hawks, and anhingas. You can also get a glimpse at over 60 species of butterflies.
After a day full of sightseeing Orlando has plenty of nightlife to enjoy. There’s a bustling live music scene that runs the gamut from EDM to classical. You can catch a touring Broadway show or opt for a local production. Downtown Orlando’s dining options are extensive, so you can indulge in an old favorite or sample a new kind of cuisine. If you’re into sports, you can cheer on Orlando’s professional basketball team. Fun and excitement are easy to find no matter what you’re into.
Start planning your trip to Orlando today and see why it’s one of America’s favorite vacation spots.
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.
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 (O'Hare) to Orlando the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago O'Hare 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.