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Find low faresSouthwest® flights from Cleveland to Chicago (Midway) from $49
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1 Passenger
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today
Low fares from Cleveland to Chicago (Midway)
$
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 04/07/2026
One-way
Choice
From
$49
Seen: 20 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 03/03/2026
One-way
Choice
From
$49
Seen: 18 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 04/01/2026
One-way
Choice
From
$49
Seen: 17 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 04/21/2026
One-way
Choice
From
$49
Seen: 15 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 04/29/2026
One-way
Choice
From
$49
Seen: 4 hrs ago
Cleveland (CLE)to
Chicago (Midway) (MDW)
Depart: 02/25/2026
One-way
Choice
From
$49
Seen: 19 hrs ago
Explore flights from Cleveland to Chicago (Midway)
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Flight Details
Departing from:
Hopkins International Airport
Arriving at:
Chicago Midway International Airport
Average flight time:
1 hour 16 minutes
Distance:
307 miles
Route Information
89† 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 Cleveland to Chicago (Midway) is 1 hour 16 minutes.
There are 89 weekly flights from Cleveland to Chicago (Midway) on Southwest Airlines.
Yes, Southwest flies nonstop from Cleveland to Chicago (Midway) 3 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Cleveland to Chicago (Midway) 3 times per day on Saturdays and Sundays.
To find the lowest fares by day and time to fly Cleveland to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
You can rent a car at Chicago Midway International Airport book yours with your flight.
Yes! Flights from Cleveland to Chicago (Midway)—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.