Southwest® flights from Orlando to Chicago (Midway) from $46
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Low fares from Orlando to Chicago (Midway)
$
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 02/11/2026
One-way
Basic
From
$46
Seen: 1 hour ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 02/11/2026
One-way
Choice
From
$63
Seen: 1 hour ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 02/13/2026
One-way
Basic
From
$83
Seen: 51 minutes ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 02/05/2026
One-way
Basic
From
$83
Seen: 1 hour ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 01/24/2026
One-way
Basic
From
$83
Seen: 16 minutes ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 01/08/2026
One-way
Basic
From
$83
Seen: 1 hour ago
Explore flights from Orlando to Chicago (Midway)
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Travel tips for your next Southwest flight
How to board the plane earlier on open seating flights departing on or before January 26, 2026:
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
- Purchase EarlyBird Check-In®1 for automatic check-in and a better boarding position.
- Purchase Upgraded Boarding2 to get an A1-A15 boarding position (depending on availability).
- Purchase a Business Select® fare or upgrade to Business Select to get a guaranteed A1-A15 boarding position.
Enjoy movies, sips, and snacks during your flight.
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.
Make the most of our Rapid Rewards® Program.
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
Flight Details
Departing from:
Orlando International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
2 hours 45 minutes
Distance:
990 miles
Route Information
156† Weekly flights
- 6‡ Nonstop flights per day Monday through Friday
- 8‡ Nonstop flights on Saturday
- 8‡ Nonstop flights on Sunday
† Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.
‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.
Explore Chicago (Midway)
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.
Questions we hear the most
The average flight time from Orlando to Chicago (Midway) is 2 hours 45 minutes.
There are 156 weekly flights from Orlando to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Orlando to Chicago (Midway) 6 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Orlando to Chicago (Midway) 8 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Orlando to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Orlando to Chicago (Midway)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Check the status of your upcoming Southwest flight.
Check out the Southwest Airlines® Help Center for answers about everything Southwest.
Explore Flights from Other Popular Origins
Popular Flights from Orlando
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.
3Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
4Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
5Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
6Internet 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.
7Flights 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.