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Flights from Cleveland to Chicago Starting at £35

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Cleveland to Chicago

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Cleveland to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Southwest Airlines
From £35
American Airlines
From £39
Delta Air Lines
From £53
United Airlines
From £58
Frontier Airlines
From £59
Sun Country Airlines
From £81
Alaska Airlines
From £160
ANA airlines

Find more flights and airlines

Alternative Routes from Cleveland to Chicago

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Cleveland to Chicago.

  • Cheapest
    Southwest Airlines
    CLE
    20:50
    1h 20m
    Direct
    MDW
    21:10
    Cleveland Hopkins International Airport - Midway International Airport
    Fri, Apr 5Southwest Airlines
    £35
  • American Airlines
    CLE
    06:38
    1h 32m
    Direct
    ORD
    07:10
    Cleveland Hopkins International Airport - O'Hare International Airport
    Wed, May 8American Airlines
    £39
  • American Airlines
    CLE
    06:38
    1h 32m
    Direct
    ORD
    07:10
    Cleveland Hopkins International Airport - O'Hare International Airport
    Wed, May 8American Airlines
    £39
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Cleveland (CLE) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Cleveland to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much are flights from Cleveland (CLE) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around £215.
  • How long is the flight from Cleveland (CLE) to Chicago (CHI)?

    It takes about 1 hour 31 minutes to fly from Cleveland (CLE) to Chicago (CHI).
  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.
  • What are the most popular airlines that fly from Cleveland (CLE) to Chicago (CHI)?

    Airlines with flights from Cleveland (CLE) to Chicago (CHI): Emirates, American Airlines, United Airlines, Alaska Airlines, Qatar Airways, Gulf Air, Southwest Airlines, Iberia and British Airways.
  • What's the most popular airline for direct flights from Cleveland (CLE) to Chicago (CHI)?

    United Airlines operates 1 direct flights from Cleveland (CLE) to Chicago (CHI).
  • How many airports in Chicago (CHI)?

Flight Information from Cleveland to Chicago

Cheapest direct flight price

£35

Cheapest return ticket price

£70

Cheapest month

October

Peak season for travel

September