Cheap Flights from Cleveland to Chicago

Compare Cleveland to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from Cleveland to Chicago

Looking for a cheap last-minute deal or the best return flight from Cleveland to Chicago? Find the lowest prices on one-way and return tickets right here.

Chicago.SAR 225 per passenger.Departing Sat, 24 May.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Cleveland Hopkins International on Sat, 24 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 225, select.

Chicago.SAR 269 per passenger.Departing Tue, 25 Mar.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Cleveland Hopkins International on Tue, 25 Mar, arriving in Chicago Midway.Price includes taxes and charges.From SAR 269, select.

Chicago.SAR 270 per passenger.Departing Tue, 15 Apr.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Cleveland Hopkins International on Tue, 15 Apr, arriving in Chicago Midway.Price includes taxes and charges.From SAR 270, select.

Chicago.SAR 300 per passenger.Departing Tue, 1 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Cleveland Hopkins International on Tue, 1 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 300, select.

Chicago.SAR 352 per passenger.Departing Mon, 2 Jun.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Cleveland Hopkins International on Mon, 2 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 352, select.

Chicago.SAR 428 per passenger.Departing Mon, 5 May.One-way flight with United.Outbound direct flight with United departs from Cleveland Hopkins International on Mon, 5 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From SAR 428, select.

Chicago.SAR 428 per passenger.Departing Thu, 24 Apr.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cleveland Hopkins International on Thu, 24 Apr, arriving in Chicago Midway.Price includes taxes and charges.From SAR 428, select.

Chicago.SAR 430 per passenger.Departing Mon, 2 Jun.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Cleveland Hopkins International on Mon, 2 Jun, arriving in Chicago Midway.Price includes taxes and charges.From SAR 430, select.

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.

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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	SAR 225
Cheapest month to fly	May
Average flight time	1 hr, 25 mins
Most popular airline	Alaska Airlines
Average flights per week	526

Finding cheap flights from Cleveland to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Cleveland to Chicago?

The best price we found for a return flight from Cleveland to Chicago is SAR 448. 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.

How long does it take to fly from Cleveland to Chicago?

1 hour and 24 minutes is the average flight time from Cleveland to Chicago.

Which airlines fly direct from Cleveland to Chicago?

Alaska Airlines, American Airlines and Qatar Airways fly direct from Cleveland to Chicago.

How many flights are there a week from Cleveland to Chicago?

As of March 2025, there are 526 flights per week flying from Cleveland to Chicago.

When is the cheapest time to fly from Cleveland to Chicago?

The cheapest month to fly from Cleveland to Chicago is usually March 2025.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Cleveland, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from SAR 448.

Which upcoming date is cheapest to fly from Cleveland to Chicago on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Cleveland to Chicago on Tuesday, 25 March 2025.

Can I get a direct flight from Cleveland to Chicago?

Yes – the average flight time is 1 hour and 24 minutes.

How can I get the best flight deal from Cleveland to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Cleveland to Chicago with?

The cheapest airline that flies to Chicago is Frontier Airlines. And the cheapest airline that flies to Chicago O'Hare International Airport is Southwest Airlines.

How to find cheap flights to Chicago from Cleveland

Looking for cheap tickets from Cleveland to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Cleveland to Chicago. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Chicago from Cleveland from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Flex your dates to find the best Cleveland-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Cleveland.
Set up a Price Alert. You can easily track the fare of your cheap Cleveland-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Cleveland and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
Find the cheapest Business class flights from Cleveland and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Cleveland to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

Combine your flight to Chicago from Cleveland with hotels and car hire

Once you've secured your cheap flight ticket from Cleveland to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.