Cheap flights from Cleveland to Chicago from $81

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cleveland averaging around $257.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $462. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $685.

Flying to Chicago O'Hare Intl Airport from Cleveland in the morning is the least expensive time of day to depart. momondo users have found prices as low as $480 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $867. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Cleveland Hopkins Intl to Chicago O'Hare Intl for the best Cleveland Hopkins Intl - Chicago O'Hare Intl flight prices

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport from Cleveland for as low as $198 on momondo.

There are 4 cabin classes available to choose from on Cleveland to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport.

As of September 2026, prices for Cleveland to Chicago O'Hare Intl Airport flights are approximately 37% cheaper when compared to flights at the same time last year.

United Airlines is the most popular carrier operating from Cleveland Hopkins Intl to Chicago O'Hare Intl

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Cleveland according to our data. United Airlines is the first choice among our users, with 64% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 48 flights per day flying from Cleveland to Chicago O'Hare Intl Airport. The most common time of day flights depart is 2:00PM, with 54% of flights taking off in the afternoon.

As of September 2026, 336 flights take off from Cleveland and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Mon, with 20% of weekly flights taking off on this day.