Trade the City Beautiful for the City in a Garden with a flight on Southwest Airlines. Southwest flies from Orlando International Airport to Chicago O’Hare International Airport with ticket prices that’ll make choosing to get away simple. If you have flexible travel dates, explore our Low Fare Calendar to find low fares within your travel window. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.
See what Chi-Town has to offer—book your next flight to Chicago (O’Hare) now.
Orlando, FL to Chicago (O'Hare), IL
departing on 7/11
one-way starting at*$89
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 42 travel days available.
|Departing from||Orlando International Airport (MCO)|
|Arriving at||Chicago O'Hare International Airport (ORD)|
|Average flight time||3 hours 5 minutes|
|2‡||Nonstop flights per day Monday through Friday|
|3‡||Nonstop flights on Saturday|
|2‡||Nonstop flights on Sunday|
Other popular flights from Orlando:View our interactive map
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 6/1/2023 and 6/30/2023. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 6/1/2023 and 6/30/2023.
The thrills you’ll find when you deplane at Chicago O’Hare International Airport are different than those on the menu back home, but that doesn’t make them any less exciting. If you start off your visit with a ride on the CTA Blue Line ‘L’ train, not only will you enjoy the excitement of sightseeing from a birds-eye view but you’ll get a chance to do some up close and personal people watching. Public transit denizens can teach you a lot about a city—get a crash course in the citizens of Chicago’s 77 neighborhood areas.
If you’re homesick for a specific kind of excitement, head to Navy Pier in the Streeterville neighborhood. Here you’ll find fine and casual dining, museums, shopping, and a big, beautiful Ferris wheel. Take a ride to the top and look out across the lake or over the city. Want more heights and skyline? Book a visit to the Skydeck of the Willis Tower (or Sears Tower as most locals still call it). From all the way up there, on a clear day you can see straight to Indiana.
Hungry for more Chicago? Make a meal of your trip by planning your days around the best that the city serves up. Fans of fine dining should explore Restaurant Row on Randolph Street in the West Loop; favorers of more humble flavors can pop into nearly any out-of-the-way eatery and find a delicious dish. Get ready to sink your teeth into everything the Second City has to offer.
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 Chicago (O'Hare) 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 (O'Hare) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Orlando International Airport to Chicago O'Hare 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 (O'Hare), 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.