Southwest® flights from Chicago (Midway) to Orlando from $79

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Low fares from Chicago (Midway) to Orlando

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Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/03/2026

One-way

Basic

From
$79
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/10/2026

One-way

Basic

From
$79
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/03/2026

One-way

Choice

From
$79
Seen: 13 hrs ago

Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/10/2026

One-way

Choice

From
$79
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/02/2026

One-way

Basic

From
$90
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Orlando (MCO)
Depart: 03/04/2026

One-way

Basic

From
$90
Seen: 13 hrs ago
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Explore flights from Chicago (Midway) to Orlando

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.

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