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Cheap flights from Cleveland to Chicago from $59

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
10:14 am - 11:12 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 58mnonstop
American Airlines Logo
9:09 pm - 11:48 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 39mnonstop
$127American Airlines
Sat, Dec 12 - Sat, Dec 19
Frontier Logo
9:29 pm - 10:59 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
26h 30m1 stop Tampa
Frontier Logo
5:58 am - 4:35 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
9h 37m1 stop Atlanta Hartsfield-Jackson
$133Frontier
Sat, Dec 19 - Tue, Dec 22
American Airlines Logo
8:16 am - 9:11 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 55mnonstop
American Airlines Logo
6:59 am - 9:35 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 36mnonstop
$139American Airlines
Tue, Dec 1 - Sat, Dec 5
American Airlines Logo
12:40 pm - 1:33 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 53mnonstop
American Airlines Logo
10:03 pm - 12:41 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 38mnonstop
$139American Airlines
Tue, Jan 19 - Tue, Jan 19
Frontier Logo
5:18 pm - 1:08 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
8h 50m1 stop Orlando
Frontier Logo
7:59 am - 12:37 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
15h 38m1 stop Tampa
$143Frontier
Sat, Dec 5 - Mon, Dec 7
Frontier Logo
7:00 am - 3:30 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
9h 30m1 stop Orlando
Frontier Logo
4:00 pm - 12:56 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
7h 56m1 stop Atlanta Hartsfield-Jackson
$143Frontier
Sat, Dec 12 - Wed, Dec 16
United Airlines Logo
8:56 am - 9:45 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 49mnonstop
United Airlines Logo
8:50 am - 11:36 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 46mnonstop
$153United Airlines
Wed, Jan 20 - Mon, Jan 25
United Airlines Logo
5:56 pm - 6:36 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 40mnonstop
United Airlines Logo
9:50 pm - 12:14 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 24mnonstop
$153United Airlines
Tue, Dec 8 - Thu, Dec 10
Delta Logo
6:10 am - 10:59 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
5h 49m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:02 pm - 11:59 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
5h 57m1 stop Detroit Metropolitan Wayne County
$157Delta
Tue, Dec 8 - Tue, Dec 8
Delta Logo
10:37 am - 1:04 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
3h 27m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:28 pm - 12:03 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
5h 35m1 stop Detroit Metropolitan Wayne County
$157Delta
Tue, Jan 19 - Tue, Jan 19

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American Airlines flights from Cleveland to Chicago O'Hare Intl Airport

Our best American Airlines deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 12
CLE10:14 amCleveland Hopkins Intl
1h 58m
ORD11:12 amChicago O'Hare Intl
Dec 19
ORD9:09 pmChicago O'Hare Intl
1h 39m
CLE11:48 pmCleveland Hopkins Intl
$127
American Airlines
Dec 1
CLE8:16 amCleveland Hopkins Intl
1h 55m
ORD9:11 amChicago O'Hare Intl
Dec 2
ORD7:20 pmChicago O'Hare Intl
1h 37m
CLE9:57 pmCleveland Hopkins Intl
$139
American Airlines
Dec 5
CLE5:16 amCleveland Hopkins Intl
1h 44m
ORD6:00 amChicago O'Hare Intl
Dec 7
ORD9:30 amChicago O'Hare Intl
1h 34m
CLE12:04 pmCleveland Hopkins Intl
$154

Frontier flights from Cleveland to Chicago O'Hare Intl Airport

Our best Frontier deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
Frontier
Dec 19
CLE9:29 pmCleveland Hopkins Intl
26h 30m
1 stop
ORD10:59 pmChicago O'Hare Intl
Dec 22
ORD5:58 amChicago O'Hare Intl
9h 37m
1 stop
CLE4:35 pmCleveland Hopkins Intl
$133
Frontier
Dec 5
CLE5:18 pmCleveland Hopkins Intl
8h 50m
1 stop
ORD1:08 amChicago O'Hare Intl
Dec 7
ORD7:59 amChicago O'Hare Intl
15h 38m
1 stop
CLE12:37 amCleveland Hopkins Intl
$143
Frontier
Dec 12
CLE3:06 pmCleveland Hopkins Intl
11h 02m
1 stop
ORD1:08 amChicago O'Hare Intl
Dec 14
ORD7:59 amChicago O'Hare Intl
15h 38m
1 stop
CLE12:37 amCleveland Hopkins Intl
$144

momondo Fare Finder

 
Use the filters below to find and compare flights from Cleveland to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 12/12

10:14 am-11:12 am

Nonstop1h 58m

Chicago O'Hare Intl

Sat 12/19

9:09 pm-11:48 pm

Nonstop1h 39m

$127

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 12/19

9:29 pm-10:59 pm

1 stop26h 30m

Chicago O'Hare Intl

Tue 12/22

5:58 am-4:35 pm

1 stop9h 37m

$133

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Tue 12/1

8:16 am-9:11 am

Nonstop1h 55m

Chicago O'Hare Intl

Sat 12/5

6:59 am-9:35 am

Nonstop1h 36m

$139

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Tue 1/19

12:40 pm-1:33 pm

Nonstop1h 53m

Chicago O'Hare Intl

Tue 1/19

10:03 pm-12:41 am

Nonstop1h 38m

$139

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 12/5

5:18 pm-1:08 am

1 stop8h 50m

Chicago O'Hare Intl

Mon 12/7

7:59 am-12:37 am

1 stop15h 38m

$143

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 12/12

7:00 am-3:30 pm

1 stop9h 30m

Chicago O'Hare Intl

Wed 12/16

4:00 pm-12:56 am

1 stop7h 56m

$143

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Wed 1/20

8:56 am-9:45 am

Nonstop1h 49m

Chicago O'Hare Intl

Mon 1/25

8:50 am-11:36 am

Nonstop1h 46m

$153
Quickest round-trip

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Tue 12/8

5:56 pm-6:36 pm

Nonstop1h 40m

Chicago O'Hare Intl

Thu 12/10

9:50 pm-12:14 am

Nonstop1h 24m

$153

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Tue 12/8

6:10 am-10:59 am

1 stop5h 49m

Chicago O'Hare Intl

Tue 12/8

5:02 pm-11:59 pm

1 stop5h 57m

$157

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Tue 1/19

10:37 am-1:04 pm

1 stop3h 27m

Chicago O'Hare Intl

Tue 1/19

5:28 pm-12:03 am

1 stop5h 35m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Cleveland to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Cleveland and Chicago O'Hare Intl Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $267 to $418.
The lowest price recently found on this route was $127.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cleveland averaging around $277.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

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 $478. 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 $682.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

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 $493 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $894. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cleveland Hopkins Intl to Chicago O'Hare Intl flight route?

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

How far in advance should I book a flight from Cleveland to Chicago O'Hare Intl Airport?

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 $324 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.

What cabin class options are available on Cleveland to Chicago O'Hare Intl Airport flights?

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.

Can stopping save me money on Cleveland to Chicago O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Cleveland to Chicago O'Hare Intl Airport.

How have Cleveland to Chicago O'Hare Intl Airport flight prices changed over time?

As of November 2026, prices for Cleveland to Chicago O'Hare Intl Airport flights are approximately 24% cheaper when compared to flights at the same time last year.

When to book flights from Cleveland to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Cleveland to Chicago O'Hare Intl Airport (CLE to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago O'Hare Intl Airport

Best Price Found

$59

Fastest flight time

1h 30m

Direct flights

Tue, Wed, Thu, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Cleveland in the past 72 hours is $59. The best round-trip flight deal from Cleveland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $127.
The fastest flight from Cleveland to Chicago O'Hare Intl Airport takes 1h 30m
Direct flights go from Cleveland to Chicago O'Hare Intl Airport on Tuesday, Wednesday, Thursday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
Search flight deals

Frequently asked questions about flying from Cleveland to Chicago O'Hare Intl Airport

  • How far is Cleveland Hopkins Intl to Chicago O'Hare Intl by plane?

    Cleveland Hopkins Intl and Chicago O'Hare Intl are 321.6 mi apart from one another. 1h 30m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport were last updated today.

  • How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cleveland to Chicago O'Hare Intl Airport?

  • What is the most popular airline from Cleveland to Chicago O'Hare Intl Airport?

Best airlines flying from Cleveland to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Cleveland to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $117Free CancellationRating
7.0
12,233 reviews
Search American Airlines flights
United AirlinesPriceFrom $134Free CancellationRating
7.3
10,493 reviews
Search United Airlines flights
FrontierPriceFrom $146Free CancellationRating
5.5
2,505 reviews
Search Frontier flights

  • United Airlines Flights From Cleveland to Chicago O'Hare Intl Airport

    United Airlines flight deals from Cleveland to Chicago O'Hare Intl Airport start from $134 round-trip. Over the 39 United Airlines flights for this route in a normal week, average airfare is usually $336 round-trip - but some users have found much cheaper deals with momondo.

  • American Airlines Flights From Cleveland to Chicago O'Hare Intl Airport

    Across 12,234 American Airlines reviews on momondo, the average score is 7.0/10. American Airlines flies from Cleveland to Chicago O'Hare Intl Airport about 29 times each week, with ticket deals ranging from $117 to $266. Price data is based on momondo searches in the last 72 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Oak Brook
Rosemont
Gurnee
Orland Park
Joliet
Naperville
New Buffalo
Kenosha
Hammond
Aurora
Racine
Elgin
Janesville
Skokie
Waukegan

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Cleveland to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Cleveland to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Cleveland on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Cleveland to Chicago?

Once you have performed a search for Cleveland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Cleveland to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Cleveland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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