Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Orlando to Chicago (O'Hare) now!
Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from Orlando to Chicago (O'Hare) now!
Orlando, FL to Chicago (O'Hare), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 18 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
We make bag-checking a breeze with our flexible baggage policy. Here’s how to make your journey even smoother:
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Fare | Fly one-way from $108 (departing on 3/11)* |
|---|---|
| Departing from | Orlando International Airport (MCO) |
| Arriving at | Chicago O'Hare International Airport (ORD) |
| Average flight time | Unavailable |
| Distance | 1005 miles |
| 119† | Weekly flights |
|---|---|
| 0 | Nonstop flight per day Monday through Friday |
| 0 | Nonstop flight on Saturday |
| 0 | Nonstop flight on Sunday |
Other popular flights from Orlando:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 2/1/2025 and 2/28/2025. Note: route may not operate every day of the week.
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 18 travel days available. Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com.
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.
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3First and second checked bags. Weight and size limits apply.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
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.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.