Cheap flights from Cleveland to Chicago from $59

The month of May is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $251. If you’re not able to fly to Chicago in May, then September is your next best option. Flight prices from Cleveland to Chicago during September average around $264.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $453. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $642.

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cleveland to Chicago during this time can be as low as $472. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $731.

Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland Hopkins Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $321 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cleveland for as low as $198 on momondo.

There are 4 cabin classes available to choose from on Cleveland to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Cleveland to Chicago.

As of September 2026, prices for Cleveland to Chicago flights are approximately 29% more expensive when compared to flights at the same time last year.

Southwest, United Airlines, and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Chicago

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Cleveland according to our data. United Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

The number of flights available between Cleveland and Chicago is 61 per day as of September 2026. The most frequent departure time is 2:00PM, with 54% of daily flights leaving in the afternoon.

The number of flights available between Cleveland and Chicago is 427 per week as of September 2026. The most frequent departure day is Fri, with 17% of weekly flights leaving on this day.