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Cheap flights from Cleveland to Chicago from $59

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Chicago departing on 11/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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
5:06 am - 5:57 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 51mnonstop
American Airlines Logo
5:39 pm - 8:16 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 37mnonstop
$134American Airlines
Fri, Nov 27 - Sat, Jan 9
American Airlines Logo
9:45 am - 10:32 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 47mnonstop
American Airlines Logo
6:40 am - 9:15 amORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 35mnonstop
$134American Airlines
Fri, Sep 11 - Mon, Sep 14
Frontier Logo
7:00 am - 6:23 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
12h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:21 pm - 12:04 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
15h 43m1 stop Atlanta Hartsfield-Jackson
$137Frontier
Sat, Sep 19 - Sat, Sep 26
Frontier Logo
7:00 am - 6:23 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
12h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:20 am - 8:52 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
13h 32m1 stop Atlanta Hartsfield-Jackson
$137Frontier
Sat, Oct 3 - Tue, Oct 6
Frontier Logo
7:00 am - 6:23 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
12h 23m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
7:21 pm - 12:04 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
15h 43m1 stop Atlanta Hartsfield-Jackson
$137Frontier
Sat, Sep 12 - Sat, Sep 19
United Airlines Logo
8:23 am - 9:00 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 37mnonstop
United Airlines Logo
4:15 pm - 6:47 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 32mnonstop
$150United Airlines
Thu, Sep 3 - Sun, Sep 6
United Airlines Logo
4:40 pm - 5:24 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 44mnonstop
United Airlines Logo
1:30 pm - 3:59 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 29mnonstop
$150United Airlines
Wed, Sep 9 - Fri, Sep 11
American Airlines Logo
8:49 pm - 9:35 pmCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
1h 46mnonstop
American Airlines Logo
9:16 pm - 11:51 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
1h 35mnonstop
$150American Airlines
Fri, Sep 11 - Tue, Sep 15
Delta Logo
6:10 am - 10:29 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
5h 19m1 stop Detroit Metropolitan Wayne County
Delta Logo
8:29 am - 1:39 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
4h 10m1 stop Detroit Metropolitan Wayne County
$157Delta
Sat, Oct 17 - Mon, Oct 19
Delta Logo
8:28 am - 10:37 amCLE  Cleveland Hopkins Intl-ORD Chicago O'Hare Intl
3h 09m1 stop Detroit Metropolitan Wayne County
Delta Logo
7:05 am - 1:40 pmORD  Chicago O'Hare Intl-CLE Cleveland Hopkins Intl
5h 35m1 stop Detroit Metropolitan Wayne County
$157Delta
Wed, Sep 9 - Sat, Sep 12

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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
Sep 12
CLE7:00 amCleveland Hopkins Intl
12h 23m
1 stop
ORD6:23 pmChicago O'Hare Intl
Sep 19
ORD7:21 pmChicago O'Hare Intl
15h 43m
1 stop
CLE12:04 pmCleveland Hopkins Intl
$137
Frontier
Sep 7
CLE6:45 amCleveland Hopkins Intl
26h 08m
1 stop
ORD7:53 amChicago O'Hare Intl
Sep 12
ORD7:21 pmChicago O'Hare Intl
15h 43m
1 stop
CLE12:04 pmCleveland Hopkins Intl
$138
Frontier
Sep 8
CLE5:15 pmCleveland Hopkins Intl
19h 36m
1 stop
ORD11:51 amChicago O'Hare Intl
Sep 12
ORD7:21 pmChicago O'Hare Intl
15h 43m
1 stop
CLE12:04 pmCleveland Hopkins Intl
$139

Delta flights from Cleveland to Chicago O'Hare Intl Airport

Our best Delta deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
Delta
Sep 9
CLE8:28 amCleveland Hopkins Intl
5h 31m
1 stop
ORD12:59 pmChicago O'Hare Intl
Sep 10
ORD8:55 amChicago O'Hare Intl
3h 45m
1 stop
CLE1:40 pmCleveland Hopkins Intl
$157
Delta
Sep 9
CLE8:28 amCleveland Hopkins Intl
5h 31m
1 stop
ORD12:59 pmChicago O'Hare Intl
Sep 11
ORD1:55 pmChicago O'Hare Intl
6h 05m
1 stop
CLE9:00 pmCleveland Hopkins Intl
$164
Delta
Sep 8
CLE4:00 pmCleveland Hopkins Intl
5h 30m
1 stop
ORD8:30 pmChicago O'Hare Intl
Sep 12
ORD2:00 pmChicago O'Hare Intl
3h 40m
1 stop
CLE6:40 pmCleveland Hopkins Intl
$178

momondo Fare Finder

 
Customize your flight search to find flights from Cleveland to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 17, 2026.
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

Fri 11/27

5:06 am-5:57 am

Nonstop1h 51m

Chicago O'Hare Intl

Sat 1/9

5:39 pm-8:16 pm

Nonstop1h 37m

$134

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Fri 9/11

9:45 am-10:32 am

Nonstop1h 47m

Chicago O'Hare Intl

Mon 9/14

6:40 am-9:15 am

Nonstop1h 35m

$134

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 9/19

7:00 am-6:23 pm

1 stop12h 23m

Chicago O'Hare Intl

Sat 9/26

7:21 pm-12:04 pm

1 stop15h 43m

$137

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 10/3

7:00 am-6:23 pm

1 stop12h 23m

Chicago O'Hare Intl

Tue 10/6

6:20 am-8:52 pm

1 stop13h 32m

$137

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 9/12

7:00 am-6:23 pm

1 stop12h 23m

Chicago O'Hare Intl

Sat 9/19

7:21 pm-12:04 pm

1 stop15h 43m

$137
Quickest round-trip

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Thu 9/3

8:23 am-9:00 am

Nonstop1h 37m

Chicago O'Hare Intl

Sun 9/6

4:15 pm-6:47 pm

Nonstop1h 32m

$150

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Wed 9/9

4:40 pm-5:24 pm

Nonstop1h 44m

Chicago O'Hare Intl

Fri 9/11

1:30 pm-3:59 pm

Nonstop1h 29m

$150

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Fri 9/11

8:49 pm-9:35 pm

Nonstop1h 46m

Chicago O'Hare Intl

Tue 9/15

9:16 pm-11:51 pm

Nonstop1h 35m

$150

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Sat 10/17

6:10 am-10:29 am

1 stop5h 19m

Chicago O'Hare Intl

Mon 10/19

8:29 am-1:39 pm

1 stop4h 10m

$157

ClevelandChicago

CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl

CLEORD

Cleveland Hopkins Intl

Wed 9/9

8:28 am-10:37 am

1 stop3h 09m

Chicago O'Hare Intl

Sat 9/12

7:05 am-1:40 pm

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 $207 to $359.
The lowest price recently found on this route was $137.

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 $264.

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 $465. 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 $692.

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 $482 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $874. 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 $317 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 August 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

Every day
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 $134.
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 every day.
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 $137Free CancellationRating
7.1
11,946 reviews
Search American Airlines flights
United AirlinesPriceFrom $139Free CancellationRating
7.4
10,107 reviews
Search United Airlines flights
FrontierPriceFrom $143Free CancellationRating
5.6
2,678 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 $139 round-trip. Over the 51 United Airlines flights for this route in a normal week, average airfare is usually $317 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,944 American Airlines reviews on momondo, the average score is 7.1/10. American Airlines flies from Cleveland to Chicago O'Hare Intl Airport about 40 times each week, with ticket deals ranging from $137 to $269. 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
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Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
Evanston
South Holland

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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