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Cheap flights from Cleveland to Chicago from $104

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 11/21. 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.
Frontier Logo
5:30 am - 12:26 pmCLE-ORD
7h 56m1 stop
Frontier Logo
5:00 am - 10:51 pmORD-CLE
16h 51m1 stop
$181Frontier
Find Deal
Fri, Oct 31 - Sun, Nov 2
Frontier Logo
7:51 pm - 7:26 amCLE-ORD
12h 35m2 stops
Frontier Logo
6:00 am - 12:22 pmORD-CLE
5h 22m1 stop
$183Frontier
Find Deal
Thu, Oct 30 - Sat, Nov 1
Multiple Airlines Logo
6:15 am - 4:25 pmCLE-ORD
11h 10m1 stop
Multiple Airlines Logo
4:22 pm - 11:30 amORD-CLE
18h 08m2 stops
$184Multiple Airlines
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Thu, Nov 27 - Tue, Dec 2
Multiple Airlines Logo
7:51 pm - 10:41 amCLE-ORD
15h 50m1 stop
Multiple Airlines Logo
10:52 am - 2:14 pmORD-CLE
26h 22m2 stops
$185Multiple Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3
JetBlue Logo
9:00 am - 5:44 pmCLE-ORD
9h 44m1 stop
JetBlue Logo
10:45 am - 8:40 pmORD-CLE
8h 55m1 stop
$207JetBlue
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Wed, Jan 28 - Fri, Feb 6
United Airlines Logo
11:00 am - 11:32 amCLE-ORD
1h 32mnonstop
United Airlines Logo
10:55 am - 1:14 pmORD-CLE
1h 19mnonstop
$215United Airlines
Find Deal
Tue, Nov 11 - Thu, Nov 27
JetBlue Logo
7:45 pm - 10:35 amCLE-ORD
15h 50m1 stop
JetBlue Logo
11:20 am - 6:46 pmORD-CLE
6h 26m1 stop
$225JetBlue
Find Deal
Tue, Nov 11 - Tue, Nov 18
United Airlines Logo
8:40 am - 9:12 amCLE-ORD
1h 32mnonstop
United Airlines Logo
9:35 pm - 11:58 pmORD-CLE
1h 23mnonstop
$228United Airlines
Find Deal
Fri, Nov 21 - Mon, Nov 24
American Airlines Logo
6:30 am - 10:42 amCLE-ORD
5h 12m1 stop
American Airlines Logo
6:48 am - 9:12 amORD-CLE
1h 24mnonstop
$238American Airlines
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Fri, Nov 21 - Mon, Nov 24
American Airlines Logo
6:30 am - 10:42 amCLE-ORD
5h 12m1 stop
American Airlines Logo
5:58 pm - 8:20 pmORD-CLE
1h 22mnonstop
$241American Airlines
Find Deal
Sat, Nov 15 - Sat, Nov 22

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
Oct 31
CLE5:30 amCleveland Hopkins Intl
7h 56m
1 stop
ORD12:26 pmChicago O'Hare Intl
Nov 2
ORD5:00 amChicago O'Hare Intl
16h 51m
1 stop
CLE10:51 pmCleveland Hopkins Intl
$181
Find similar
Frontier
Oct 30
CLE7:51 pmCleveland Hopkins Intl
12h 35m
2 stops
ORD7:26 amChicago O'Hare Intl
Nov 1
ORD6:00 amChicago O'Hare Intl
5h 22m
1 stop
CLE12:22 pmCleveland Hopkins Intl
$183
Find similar
Frontier
Nov 8
CLE8:30 amCleveland Hopkins Intl
7h 38m
1 stop
ORD3:08 pmChicago O'Hare Intl
Nov 9
ORD6:30 pmChicago O'Hare Intl
5h 24m
1 stop
CLE12:54 amCleveland Hopkins Intl
$188
Find similar

JetBlue flights from Cleveland to Chicago O'Hare Intl Airport

Our best JetBlue deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
JetBlue
Jan 28
CLE9:00 amCleveland Hopkins Intl
9h 44m
1 stop
ORD5:44 pmChicago O'Hare Intl
Feb 6
ORD10:45 amChicago O'Hare Intl
8h 55m
1 stop
CLE8:40 pmCleveland Hopkins Intl
$207
Find similar
JetBlue
Nov 11
CLE7:45 pmCleveland Hopkins Intl
15h 50m
1 stop
ORD10:35 amChicago O'Hare Intl
Nov 18
ORD11:20 amChicago O'Hare Intl
6h 26m
1 stop
CLE6:46 pmCleveland Hopkins Intl
$225
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 October 20, 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 10/31

5:30 am-12:26 pm

1 stop7h 56m

Chicago O'Hare Intl

Sun 11/2

5:00 am-10:51 pm

1 stop16h 51m

$181

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 10/30

7:51 pm-7:26 am

2 stops12h 35m

Chicago O'Hare Intl

Sat 11/1

6:00 am-12:22 pm

1 stop5h 22m

$183

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 11/27

6:15 am-4:25 pm

1 stop11h 10m

Chicago O'Hare Intl

Tue 12/2

4:22 pm-11:30 am

2 stops18h 08m

$184

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 10/30

7:51 pm-10:41 am

1 stop15h 50m

Chicago O'Hare Intl

Mon 11/3

10:52 am-2:14 pm

2 stops26h 22m

$185

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 1/28

9:00 am-5:44 pm

1 stop9h 44m

Chicago O'Hare Intl

Fri 2/6

10:45 am-8:40 pm

1 stop8h 55m

$207

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 11/11

11:00 am-11:32 am

Nonstop1h 32m

Chicago O'Hare Intl

Thu 11/27

10:55 am-1:14 pm

Nonstop1h 19m

$215

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 11/11

7:45 pm-10:35 am

1 stop15h 50m

Chicago O'Hare Intl

Tue 11/18

11:20 am-6:46 pm

1 stop6h 26m

$225

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 11/21

8:40 am-9:12 am

Nonstop1h 32m

Chicago O'Hare Intl

Mon 11/24

9:35 pm-11:58 pm

Nonstop1h 23m

$228

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 11/21

6:30 am-10:42 am

1 stop5h 12m

Chicago O'Hare Intl

Mon 11/24

6:48 am-9:12 am

Nonstop1h 24m

$238

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 11/15

6:30 am-10:42 am

1 stop5h 12m

Chicago O'Hare Intl

Sat 11/22

5:58 pm-8:20 pm

Nonstop1h 22m

$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 $528. 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 $752.

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 $513 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $917. 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 $295 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 $172 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.

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

You could potentially save up to 11% on your flight if you consider stops on a Cleveland to Chicago O'Hare Intl Airport flight.

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

As of October 2025, prices for Cleveland to Chicago O'Hare Intl Airport flights are approximately 60% more expensive 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

$197

Fastest flight time

1h 30m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago O'Hare Intl Airport from Cleveland in the past 72 hours is $197. The best round-trip flight deal from Cleveland to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $347.
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 Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is United Airlines.
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 32m 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
FrontierPriceFrom $108Free CancellationRating
5.8
3,130 reviews
Search Frontier flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
11,024 reviews
Search American Airlines flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,991 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 44 United Airlines flights for this route in a normal week, average airfare is usually $310 round-trip - but some users have found much cheaper deals with momondo.

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

    Across 11,024 American Airlines reviews on momondo, the average score is 7.2/10. American Airlines flies from Cleveland to Chicago O'Hare Intl Airport about 47 times each week, with ticket deals ranging from $138 to $297. 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
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
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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