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Cheap flights from Cleveland to Chicago from $76

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 9/22. 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

Frontier Logo
5:30 am - 10:31 amCLE-ORD
6h 01m1 stop
Frontier Logo
2:07 pm - 12:02 amORD-CLE
8h 55m1 stop
$139Frontier
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lun., sep. 29 - lun., sep. 29
Frontier Logo
7:19 pm - 11:41 pmCLE-MDW
5h 22m1 stop
Frontier Logo
5:28 pm - 12:44 amMDW-CLE
6h 16m1 stop
$143Frontier
Find Deal
sáb., oct. 4 - vie., oct. 17
Logo
6:00 am - 11:35 amCLE-ORD
6h 35m1 stop
Logo
1:26 pm - 6:32 pmORD-CLE
28h 06m1 stop
$165
Find Deal
sáb., oct. 18 - dom., oct. 19
Southwest Logo
11:40 am - 4:35 pmCLE-MDW
5h 55m2 stops
Southwest Logo
6:40 am - 12:45 pmMDW-CLE
5h 05m1 stop
$166Southwest
Find Deal
mar., dic. 16 - sáb., ene. 10
Logo
7:40 pm - 8:18 amCLE-ORD
13h 38m1 stop
Logo
11:00 am - 5:26 pmORD-CLE
5h 26m1 stop
$169
Find Deal
vie., oct. 17 - mar., oct. 21
Southwest Logo
11:40 am - 4:35 pmCLE-MDW
5h 55m2 stops
Southwest Logo
12:50 pm - 10:05 pmMDW-CLE
8h 15m2 stops
$171Southwest
Find Deal
mar., dic. 16 - sáb., ene. 10
United Airlines Logo
6:05 pm - 6:39 pmCLE-ORD
1h 34mnonstop
United Airlines Logo
2:35 pm - 4:59 pmORD-CLE
1h 24mnonstop
$172United Airlines
Find Deal
mar., sep. 30 - mié., oct. 1
United Airlines Logo
7:00 am - 7:34 amCLE-ORD
1h 34mnonstop
United Airlines Logo
4:10 pm - 6:36 pmORD-CLE
1h 26mnonstop
$177United Airlines
Find Deal
jue., oct. 2 - mié., oct. 8
Delta Logo
12:19 pm - 6:35 pmCLE-MDW
7h 16m2 stops
Delta Logo
6:00 am - 11:43 amMDW-CLE
4h 43m1 stop
$182Delta
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mar., sep. 30 - jue., oct. 2
Delta Logo
8:05 am - 2:55 pmCLE-ORD
7h 50m1 stop
Delta Logo
1:25 pm - 12:36 amORD-CLE
10h 11m2 stops
$182Delta
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jue., oct. 16 - mar., oct. 21

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets
Frontier
Sep 29
CLE5:30 amCleveland Hopkins Intl
6h 01m
1 stop
ORD10:31 amChicago O'Hare Intl
Sep 29
ORD2:07 pmChicago O'Hare Intl
8h 55m
1 stop
CLE12:02 amCleveland Hopkins Intl
$139
Find similar
Frontier
Oct 3
CLE5:30 amCleveland Hopkins Intl
6h 01m
1 stop
ORD10:31 amChicago O'Hare Intl
Oct 6
ORD5:50 pmChicago O'Hare Intl
5h 53m
1 stop
CLE12:43 amCleveland Hopkins Intl
$143
Find similar
Frontier
Sep 25
CLE7:25 amCleveland Hopkins Intl
10h 26m
1 stop
ORD4:51 pmChicago O'Hare Intl
Sep 28
ORD7:40 amChicago O'Hare Intl
9h 15m
1 stop
CLE5:55 pmCleveland Hopkins Intl
$144
Find similar

United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets
United Airlines
Sep 30
CLE6:05 pmCleveland Hopkins Intl
1h 34m
ORD6:39 pmChicago O'Hare Intl
Oct 1
ORD2:35 pmChicago O'Hare Intl
1h 24m
CLE4:59 pmCleveland Hopkins Intl
$172
Find similar
United Airlines
Oct 2
CLE7:00 amCleveland Hopkins Intl
1h 34m
ORD7:34 amChicago O'Hare Intl
Oct 8
ORD4:10 pmChicago O'Hare Intl
1h 26m
CLE6:36 pmCleveland Hopkins Intl
$177
Find similar
United Airlines
Sep 30
CLE6:00 amCleveland Hopkins Intl
1h 30m
ORD6:30 amChicago O'Hare Intl
Oct 2
ORD7:30 amChicago O'Hare Intl
1h 24m
CLE9:54 amCleveland Hopkins Intl
$190
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cleveland to Chicago 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 septiembre 15, 2025.
Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

lun. 9/29

5:30 am-10:31 am

1 stop6h 01m

Chicago O'Hare Intl

lun. 9/29

2:07 pm-12:02 am

1 stop8h 55m

$139

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

sáb. 10/4

7:19 pm-11:41 pm

1 stop5h 22m

Chicago Midway

vie. 10/17

5:28 pm-12:44 am

1 stop6h 16m

$143

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

sáb. 10/18

6:00 am-11:35 am

1 stop6h 35m

Chicago O'Hare Intl

dom. 10/19

1:26 pm-6:32 pm

1 stop28h 06m

$165

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

mar. 12/16

11:40 am-4:35 pm

2 stops5h 55m

Chicago Midway

sáb. 1/10

6:40 am-12:45 pm

1 stop5h 05m

$166

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

vie. 10/17

7:40 pm-8:18 am

1 stop13h 38m

Chicago O'Hare Intl

mar. 10/21

11:00 am-5:26 pm

1 stop5h 26m

$169

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

mar. 12/16

11:40 am-4:35 pm

2 stops5h 55m

Chicago Midway

sáb. 1/10

12:50 pm-10:05 pm

2 stops8h 15m

$171

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

mar. 9/30

6:05 pm-6:39 pm

Nonstop1h 34m

Chicago O'Hare Intl

mié. 10/1

2:35 pm-4:59 pm

Nonstop1h 24m

$172

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

jue. 10/2

7:00 am-7:34 am

Nonstop1h 34m

Chicago O'Hare Intl

mié. 10/8

4:10 pm-6:36 pm

Nonstop1h 26m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

mar. 9/30

12:19 pm-6:35 pm

2 stops7h 16m

Chicago Midway

jue. 10/2

6:00 am-11:43 am

1 stop4h 43m

$182

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

jue. 10/16

8:05 am-2:55 pm

1 stop7h 50m

Chicago O'Hare Intl

mar. 10/21

1:25 pm-12:36 am

2 stops10h 11m

$182

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

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?

The month of August is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $187. If you’re not able to fly to Chicago in August, then April is your next best option. Flight prices from Cleveland to Chicago during April average around $242.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago 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. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $670.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cleveland to Chicago during this time can be as low as $485. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $868.

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

Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland Hopkins Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $294 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Cleveland for as low as $172 on momondo.

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

There are 4 cabin classes available to choose from on Cleveland Hopkins Intl to Chicago 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 flights?

You could potentially save up to 1% on your flight if you consider stops on a Cleveland to Chicago flight.

How have Cleveland to Chicago flight prices changed over time?

As of September 2025, prices for Cleveland to Chicago flights are approximately 9% more expensive when compared to flights at the same time last year.

When to book flights from Cleveland to Chicago

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

Cheap Cleveland to Chicago (CLE to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago

Best Price Found

$158

Fastest flight time

1h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cleveland in the past 72 hours is $158. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $276.
The fastest flight from Cleveland to Chicago takes 1h 15m
Direct flights go from Cleveland to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

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

    Cleveland Hopkins Intl and Chicago are 307.0 mi apart from one another. A reasonable flight in good conditions will take 1h 15m.

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

    Prices for flights from Cleveland Hopkins Intl Airport to Chicago are refreshed on a daily basis.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cleveland Hopkins Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Cleveland to Chicago?

  • What is the most popular airline from Cleveland to Chicago?

Best airlines flying from Cleveland to Chicago

Compare and see reviews for airlines that fly from Cleveland to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $108Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $141Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights

  • Southwest Flights From Cleveland to Chicago

    Southwest flight deals from Cleveland to Chicago start from $141 round-trip. Over the 17 Southwest flights for this route in a normal week, average airfare is usually $277 round-trip - but some users have found much cheaper deals with momondo.

  • United Airlines Flights From Cleveland to Chicago

    United Airlines (7.4/10 from 8,929 reviews) operates around 45 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $311, with deals from around $157 rare but found on momondo. Referenced prices are for round-trip Cleveland to Chicago flight 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Cleveland to Chicago. momondo saves you time and could save you money on your trip.

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

All flight searches from Cleveland to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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 can track prices for Cleveland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport