Cheap Flights from Cleveland (CLE) to Chicago (CHI)

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Find the cheapest month to fly from Cleveland to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Cleveland to Chicago flights are currently cheapest in May.

Direct flights from Cleveland to Chicago

Alternative Cleveland to Chicago routes

Looking for the cheapest, fastest or easiest route from Cleveland to Chicago? You could fly into the following airports instead.

Cleveland to Chicago: Flight information

The things to know before you go.
Cheapest flight found$94
Cheapest month to flyMay
Average flight time1 hr, 28 mins
Most popular airlineAmerican Airlines
Average flights per week646

Finding cheap flights from Cleveland to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from Cleveland to Chicago is $94. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
1 hour and 28 minutes is the average flight time from Cleveland to Chicago.
American Airlines, Alaska Airlines and Southwest Airlines fly direct from Cleveland to Chicago.
There are 690 flights per week flying from Cleveland to Chicago, as of May 2024.
The cheapest month to fly from Cleveland to Chicago is usually May.
If you're flying from Cleveland, the cheapest airport near Chicago is Chicago O'Hare International – which is 15.8 miles away from the center of Chicago. We've found flights to this airport from $94.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Cleveland to Chicago on Tuesday, May 21, 2024.
Yes – the average flight time is 1 hour and 28 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 56°F. July is typically the warmest month in Chicago, when it usually averages around 80°F. You can expect the least rain in January. The coldest month is January, with temperatures averaging 18°F. The rainiest month is August.
The cheapest airline that flies to Chicago is Spirit Airlines, and the cheapest airline that flies to Chicago O'Hare International Airport is American Airlines.

Cleveland actually earned the famous nickname “Sixth City” in the post-WWII era, due to it being the sixth most populated in the United States at the time. Interestingly enough, the city has acquired many more names throughout its history. Most Clevelanders refer to it as the North Coast due to how close it is to the Great Lake. It may seem odd, but Ohio’s treasured favorite is also where one can find the most golf courses per capita!

The destination city is not known for a major golfing scene per se, but Chi-Town has more than enough activities “on par” for tourists. It is located 308 miles to the West of Cleveland. Flight times obviously vary depending on O’Hare Airport’s daily congestion, but expect an hour from gate-to-gate. Air Canada, AirTran Airways, and Delta Air Lines are the main carriers for direct Cleveland to Chicago flights.

En Route to Cleveland Hopkins

Nine miles southwest of Cleveland’s main business district lay its chief operating airport, Cleveland Hopkins International. Geographically speaking, it is just inside the city limits. The airfield is the largest in the state of Ohio and operates as a focal flight zone for the domestic carrier Frontier Airlines.

It is the United States’ first ever municipally owned airport, not to mention the first to feature an air traffic control tower, airfield lighting system, and ground to air radio control. Numerous facility updates have been made since Cleveland Hopkins implemented its famous massive marketing campaign in 2006, which was intended to dramatically improve the passenger experience.

Nearly 10 million foreign and domestic passengers fly through the airport’s central terminal each year. CLE has a designated pet relief area at the southern end of the baggage claim area, and offers three shoe-shining stations.

Onward to Chicago

Who can ever get enough of good old Chi-Town?! This global tourist hot spot is renowned for an excellent shopping and nightlife scene. Chicago has everything you would want in a big city, so be prepared to bring enough spending cash!

For those wanting to delve away from the traditional attractions and become fully immersed in The Windy City; the National Vietnam Veterans Art Museum and Peggy Notebaert Nature Museum, offer the perfect blend of history and entertainment. The local greeter program is a great way to partake in free, guided tours of Chicago’s many diverse neighborhoods!

The Second City can certainly be expensive to visit, so save big on airfare by bookingcheap flights from Cleveland to Chicago through Skyscanner. Instant savings are on their way into your pocket. Enjoy!

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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.