Cheap flights from Chicago to Cleveland from $59

In general, December is the cheapest month to fly from Chicago to Cleveland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $308. If you’re not able to fly to Cleveland in December, then November is your next best option. Flight prices from Chicago to Cleveland during November average around $317.

The cheapest day to depart from Chicago to Cleveland is on a Saturday when prices can be found for as low as $273. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Sunday is $518.

Our data shows that the cheapest Chicago to Cleveland flights are usually those with departure times at noon. Our users have found flights to Cleveland at noon for as low as $327. In contrast, the most expensive time of day to depart to Cleveland is in the evening when prices are around $485.

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

You are more likely to see cheaper flights to Cleveland from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Cleveland for around $431 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cleveland from Chicago for as low as $118 on momondo.

There are 4 cabin classes available to choose from on Chicago to Cleveland 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 Chicago to Cleveland.

As of November 2026, prices for Chicago to Cleveland flights are approximately 15% cheaper when compared to flights at the same time last year.

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

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Cleveland from Chicago according to our data. United Airlines is the first choice among our users, with 69% of people opting to fly with this airline when traveling to Cleveland. Keep in mind that there are 6 different airlines that fly to Cleveland on a routine basis, so you have a few additional options to choose from.

As of November 2026, 46 flights take off from Chicago and land in Cleveland each day. The most common flight departure time for this route is 9:00PM, with 42% of daily flights taking off in the evening.

As of November 2026, there are 325 flights per week flying from Chicago to Cleveland. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.