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Find low faresSouthwest® flights from Cleveland to Chicago (O'Hare) from $87
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1 Passenger
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Low fares from Cleveland to Chicago (O'Hare)
$
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 05/09/2026
One-way
Choice
From
$72
Seen: 14 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 04/11/2026
One-way
Basic
From
$72
Seen: 1 hour ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 03/14/2026
One-way
Choice
From
$80
Seen: 17 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 03/28/2026
One-way
Choice
From
$80
Seen: 17 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 03/14/2026
One-way
Basic
From
$80
Seen: 17 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 03/28/2026
One-way
Basic
From
$80
Seen: 17 hrs ago
Explore flights from Cleveland to Chicago (O'Hare)
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Flight Details
Departing from:
Hopkins International Airport
Arriving at:
O'Hare International Airport
Distance:
316 miles
Route Information
14† Weekly flights
† 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.
Questions we hear the most
There are 14 weekly flights from Cleveland to Chicago (O'Hare) on Southwest Airlines.
To find the lowest fares by day and time to fly Cleveland 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 Cleveland 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.