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Find low faresSouthwest® flights from Chicago (Midway) to Cleveland from $49
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1 Passenger
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today
Low fares from Chicago (Midway) to Cleveland
$
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 03/25/2026
One-way
Choice
From
$49
Seen: 20 hrs ago
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 04/14/2026
One-way
Choice
From
$49
Seen: 18 hrs ago
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 04/28/2026
One-way
Choice
From
$49
Seen: 15 hrs ago
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 03/10/2026
One-way
Choice
From
$49
Seen: 16 hrs ago
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 03/03/2026
One-way
Choice
From
$49
Seen: 21 hrs ago
Chicago (Midway) (MDW)to
Cleveland (CLE)
Depart: 02/25/2026
One-way
Choice
From
$49
Seen: 10 hrs ago
Explore flights from Chicago (Midway) to Cleveland
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Flight Details
Departing from:
Chicago Midway International Airport
Arriving at:
Hopkins International Airport
Average flight time:
1 hour 11 minutes
Distance:
307 miles
Route Information
85† Weekly flights
- 3‡ Nonstop flights per day Monday through Friday
- 3‡ Nonstop flights on Saturday
- 3‡ 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.
Questions we hear the most
The average flight time from Chicago (Midway) to Cleveland is 1 hour 11 minutes.
There are 85 weekly flights from Chicago (Midway) to Cleveland on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago (Midway) to Cleveland 3 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago (Midway) to Cleveland 3 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Chicago (Midway) to Cleveland with Southwest, check out our Low Fare Calendar.
You can rent a car at Hopkins International Airport book yours with your flight.
Yes! Flights from Chicago (Midway) to Cleveland—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.