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Cheap Flights from Cleveland to Chicago from $186 - KAYAK Howlong does a flightfromCleveland Hopkins Intl to Chicago take? An average nonstop flight takes 1h 22m, covering a distance of 300 miles. How long does it take to get from Chicago to Cleveland? HowlongistheflightfromChicagotoCleveland? How long is the flight from Chicago to Cleveland? Howlong does it really take to fly fromChicagotoCleveland? Here's a sample itinerary for a commercial flight plan. If you want to know the total travel time to reach Cleveland, you need to include time at the airports. Eventually, you'll be able to customize this itinerary to select other nearby airports. Cheap Flights from Chicago to Cleveland How Much is a FlightfromChicagotoCleveland? Prices shown were found by travelers like you over the past Flight Time from Chicago, IL to Cleveland, OH Howlong does it take to fly between Chicago, IL and Cleveland, OH? Get theflight duration. 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