Direct flights from Cleveland to Chicago
All flights from CLE to MDW non-stop. There are direct flights from Cleveland Hopkins International (CLE), Ohio, USA to Chicago Midway International (MDW), Illinois, USA with Southwest Airlines. 26 weekly departures are currently scheduled on this route. Departure times range from 07:30 to 21:35 depending on the schedule period. The flight distance is 307 miles (494 km). Flight time ranges from 1 hour and 10 minutes to 1 hour and 35 minutes.
Cleveland
, USA
Flight schedule from Cleveland to Chicago with Southwest Airlines
This is a weekly direct flight schedule for Southwest Airlines. Use the arrows or click on the date to change week. Click on any flight departure time to show more information and check availability.
Flight
The timetable & schedule information was updated at 2026-07-13
Cleveland to Chicago scheduled departures
Select a date to see every published non-stop departure between CLE and MDW.
CLE - MDW route facts
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Distance307 miles (494 km)
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Flight time1 hour and 10 minutes to 1 hour and 35 minutes
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Airline Southwest
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Airline alliancesLow-cost carrier
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CabinsEconomy
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AircraftBoeing 737-700 Passenger (Scimitar Winglets) , Boeing 737-800 (winglets) Passenger/BBJ2 and Boeing 737MAX 8 Passenger
Route FAQ
Direct flights from Cleveland to IL, USA
From Cleveland to Chicago
ORD Chicago O Hare International
