Southwest® flights from Orlando to Chicago (O'Hare)
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Low fares from Orlando to Chicago (O'Hare)
$
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 09/05/2026
One-way
Basic
From
$119
Seen: 17 hrs ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 09/11/2026
One-way
Basic
From
$119
Seen: 9 hrs ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 09/06/2026
One-way
Basic
From
$119
Seen: 14 hrs ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 10/30/2026
One-way
Basic
From
$119
Seen: 3 hrs ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 10/28/2026
One-way
Basic
From
$129
Seen: 17 hrs ago
Orlando (MCO)to
Chicago (Midway) (MDW)
Depart: 09/16/2026
One-way
Basic
From
$129
Seen: 17 hrs ago
Explore flights from Orlando to Chicago (O'Hare)
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Flight Details
Departing from:
Orlando International Airport
Arriving at:
O'Hare International Airport
Average flight time:
3 hours 5 minutes
Distance:
1005 miles
Route Information
89† Weekly flights
- 2‡ Nonstop flights per day Monday through Friday
- 2‡ Nonstop flights on Saturday
- 2‡ 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 (O'Hare)
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.
Questions we hear the most
The average flight time from Orlando to Chicago (O'Hare) is 3 hours 5 minutes.
There are 89 weekly flights from Orlando to Chicago (O'Hare) on Southwest Airlines.
Yes, Southwest flies nonstop from Orlando to Chicago (O'Hare) 2 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Orlando to Chicago (O'Hare) 2 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Orlando to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
You can rent a car at O'Hare International Airport book yours with your flight.
Yes! Flights from Orlando to Chicago (O'Hare)—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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