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Cheap flights from Cleveland to Chicago from $56

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 12/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
12:44 pm - 4:46 pm
CLE
-
ORD
5h 02m1 stop
American Airlines Logo
4:31 pm - 7:02 pm
ORD
-
CLE
1h 31mnonstop
$227American Airlines
Fri, Jan 16 - Sun, Jan 18
JetBlue Logo
9:30 am - 5:43 pm
CLE
-
ORD
9h 13m1 stop
JetBlue Logo
7:45 am - 8:40 pm
ORD
-
CLE
11h 55m1 stop
$229JetBlue
Wed, Jan 28 - Fri, Feb 6
United Airlines Logo
7:20 am - 8:02 am
CLE
-
ORD
1h 42mnonstop
United Airlines Logo
12:58 pm - 3:26 pm
ORD
-
CLE
1h 28mnonstop
$231United Airlines
Tue, Jan 6 - Tue, Jan 13
Delta Logo
6:29 am - 9:01 am
CLE
-
ORD
3h 32m1 stop
Delta Logo
6:50 am - 5:51 pm
ORD
-
CLE
10h 01m2 stops
$232Delta
Thu, Jan 1 - Thu, Jan 8
United Airlines Logo
2:16 pm - 2:55 pm
CLE
-
ORD
1h 39mnonstop
United Airlines Logo
7:30 am - 9:48 am
ORD
-
CLE
1h 18mnonstop
$234United Airlines
Mon, Feb 2 - Tue, Feb 17
Multiple Airlines Logo
12:18 pm - 7:45 pm
CLE
-
ORD
8h 27m1 stop
Multiple Airlines Logo
11:42 am - 5:20 pm
ORD
-
CLE
28h 38m1 stop
$235Multiple Airlines
Fri, Feb 20 - Sun, Feb 22
Delta Logo
6:00 am - 1:08 pm
CLE
-
ORD
8h 08m2 stops
Delta Logo
6:15 am - 1:16 pm
ORD
-
CLE
6h 01m2 stops
$237Delta
Thu, Jan 15 - Sun, Jan 18
Frontier Logo
12:22 pm - 12:12 am
CLE
-
ORD
12h 50m1 stop
Frontier Logo
12:39 pm - 11:13 pm
ORD
-
CLE
9h 34m1 stop
$238Frontier
Mon, Dec 15 - Fri, Dec 19
Multiple Airlines Logo
6:45 am - 12:47 pm
CLE
-
ORD
31h 02m2 stops
Multiple Airlines Logo
10:37 pm - 3:38 pm
ORD
-
CLE
16h 01m1 stop
$239Multiple Airlines
Sat, Dec 13 - Mon, Jan 12
American Airlines Logo
7:58 am - 1:22 pm
CLE
-
ORD
6h 24m1 stop
American Airlines Logo
8:08 am - 10:38 am
ORD
-
CLE
1h 30mnonstop
$241American Airlines
Tue, Jan 6 - Wed, Jan 7

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
Jan 16
CLE12:44 pmCleveland Hopkins Intl
5h 02m
1 stop
ORD4:46 pmChicago O'Hare Intl
Jan 18
ORD4:31 pmChicago O'Hare Intl
1h 31m
CLE7:02 pmCleveland Hopkins Intl
$227
Find similar
American Airlines
Jan 22
CLE7:32 pmCleveland Hopkins Intl
1h 47m
ORD8:19 pmChicago O'Hare Intl
Jan 29
ORD11:11 amChicago O'Hare Intl
1h 29m
CLE1:40 pmCleveland Hopkins Intl
$238
Find similar
American Airlines
Jan 6
CLE7:58 amCleveland Hopkins Intl
6h 24m
1 stop
ORD1:22 pmChicago O'Hare Intl
Jan 7
ORD8:08 amChicago O'Hare Intl
1h 30m
CLE10:38 amCleveland Hopkins Intl
$241
Find similar

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
Jan 1
CLE6:29 amCleveland Hopkins Intl
3h 32m
1 stop
ORD9:01 amChicago O'Hare Intl
Jan 8
ORD6:50 amChicago O'Hare Intl
10h 01m
2 stops
CLE5:51 pmCleveland Hopkins Intl
$232
Find similar
Delta
Jan 15
CLE6:00 amCleveland Hopkins Intl
8h 08m
2 stops
ORD1:08 pmChicago O'Hare Intl
Jan 18
ORD6:15 amChicago O'Hare Intl
6h 01m
2 stops
CLE1:16 pmCleveland Hopkins Intl
$237
Find similar
Delta
Jan 28
CLE12:29 pmCleveland Hopkins Intl
9h 36m
2 stops
ORD9:05 pmChicago O'Hare Intl
Feb 6
ORD10:35 amChicago O'Hare Intl
3h 32m
1 stop
CLE3:07 pmCleveland Hopkins Intl
$269
Find similar

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 December 9, 2025.
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

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 1/16

12:44 pm-4:46 pm

1 stop5h 02m

Chicago O'Hare Intl

Sun 1/18

4:31 pm-7:02 pm

Nonstop1h 31m

$227

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 1/28

9:30 am-5:43 pm

1 stop9h 13m

Chicago O'Hare Intl

Fri 2/6

7:45 am-8:40 pm

1 stop11h 55m

$229

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 1/6

7:20 am-8:02 am

Nonstop1h 42m

Chicago O'Hare Intl

Tue 1/13

12:58 pm-3:26 pm

Nonstop1h 28m

$231

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 1/1

6:29 am-9:01 am

1 stop3h 32m

Chicago O'Hare Intl

Thu 1/8

6:50 am-5:51 pm

2 stops10h 01m

$232

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 2/2

2:16 pm-2:55 pm

Nonstop1h 39m

Chicago O'Hare Intl

Tue 2/17

7:30 am-9:48 am

Nonstop1h 18m

$234

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 2/20

12:18 pm-7:45 pm

1 stop8h 27m

Chicago O'Hare Intl

Sun 2/22

11:42 am-5:20 pm

1 stop28h 38m

$235

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 1/15

6:00 am-1:08 pm

2 stops8h 08m

Chicago O'Hare Intl

Sun 1/18

6:15 am-1:16 pm

2 stops6h 01m

$237

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 12/15

12:22 pm-12:12 am

1 stop12h 50m

Chicago O'Hare Intl

Fri 12/19

12:39 pm-11:13 pm

1 stop9h 34m

$238

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 12/13

6:45 am-12:47 pm

2 stops31h 02m

Chicago O'Hare Intl

Mon 1/12

10:37 pm-3:38 pm

1 stop16h 01m

$239

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 1/6

7:58 am-1:22 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 1/7

8:08 am-10:38 am

Nonstop1h 30m

$241

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 cheapest month to fly to Chicago O'Hare Intl Airport?

The month of May is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cleveland averaging around $237.

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 $500. This is often the case because there is less demand to fly during this day of the week. On the other hand, Monday 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 $764.

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 $510 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $907. 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 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 $293 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 $88 on momondo.

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

There are 4 cabin classes available to choose from on Cleveland Hopkins Intl to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

As of December 2025, prices for Cleveland to Chicago O'Hare Intl Airport flights are approximately 13% 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

$198

Fastest flight time

1h 28m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Cleveland in the past 72 hours is $198. The best round-trip flight deal from Cleveland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $358.
The fastest flight from Cleveland to Chicago O'Hare Intl Airport takes 1h 28m
Direct flights go from Cleveland to Chicago O'Hare Intl Airport every day.
Search flight deals

  • 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 26m 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 $136Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights
FrontierPriceFrom $143Free CancellationRating
5.8
3,085 reviews
Search Frontier flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
9,088 reviews
Search United Airlines 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 $157 round-trip. Over the 49 United Airlines flights for this route in a normal week, average airfare is usually $298 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,043 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Cleveland to Chicago O'Hare Intl Airport about 31 times each week, with ticket deals ranging from $136 to $296. 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

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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