Southwest® flights from Chicago (Midway) to Orlando from $90
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Low fares from Chicago (Midway) to Orlando
$
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 03/02/2026
One-way
Basic
From
$90
Seen: 1 hour ago
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 02/03/2026
One-way
Basic
From
$90
Seen: 22 hrs ago
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 01/17/2026
One-way
Basic
From
$90
Seen: 13 hrs ago
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 02/08/2026
One-way
Basic
From
$90
Seen: 13 hrs ago
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 01/18/2026
One-way
Basic
From
$90
Seen: 13 hrs ago
Chicago (Midway) (MDW)to
Orlando (MCO)
Depart: 01/13/2026
One-way
Basic
From
$99
Seen: 12 hrs ago
Explore flights from Chicago (Midway) to Orlando
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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:
Chicago Midway International Airport
Arriving at:
Orlando International Airport
Average flight time:
2 hours 31 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 Orlando
Whether you’re visiting Orlando for business, pleasure, or a mix of both, Orlando offers a unique experience for every traveler. Located in Central Florida, expect a welcome as warm as the weather when you meet the locals. But friendly Floridians aren’t the city’s only inhabitants. A robust range of wildlife thrives in the area’s humid subtropical climate, including alligators, snakes, and armadillos. Orlando’s other claim to fame: theme parks. With more than a dozen parks to choose from, Orlando is a hot spot for ride and game lovers across the world. And if you’re looking for a bite to eat, Orlando won’t disappoint. The city’s booming restaurant scene offers delicious cuisine and dining options that range from formal to casual.
Take a trip to see Orlando’s top sites. As far as attractions go, start by visiting the Kennedy Space Center. Just a hop, skip, and jump from Orlando, Florida’s space getaway is a stop worth making. Even if you don’t catch a rocket launch that day, learning about NASA’s revolutionary journey in space exploration is enough to take you to the stars. And once you’ve worked the left side of your brain, work the right side. The Orlando Museum of Art features several exceptional collections that will arrest your attention from the moment you walk in until the moment you leave.
Questions we hear the most
The average flight time from Chicago (Midway) to Orlando is 2 hours 31 minutes.
There are 156 weekly flights from Chicago (Midway) to Orlando on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Orlando 6 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Orlando 8 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Orlando with Southwest, check out our Low Fare Calendar.
You can rent a car at Orlando International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Orlando—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 Chicago (Midway)
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.