Cheap flights from Cleveland to Chicago from $75

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 9/14. 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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Find the cheapest flights from Cleveland to Chicago (CLE-CHI)

Cheap round-trip flights

Frontier Logo
5:30 am - 3:58 pmCLE-MDW
11h 28m1 stop
Frontier Logo
4:56 pm - 12:43 amMDW-CLE
6h 47m1 stop
$132Frontier
Find Deal
Thu, Sep 25 - Thu, Oct 2
Frontier Logo
7:34 pm - 12:10 amCLE-ORD
5h 36m1 stop
Frontier Logo
5:50 pm - 12:43 amORD-CLE
5h 53m1 stop
$132Frontier
Find Deal
Thu, Sep 25 - Thu, Oct 2
Frontier Logo
7:34 pm - 11:20 pmCLE-MDW
28h 46m1 stop
Frontier Logo
5:15 pm - 12:43 amMDW-CLE
6h 28m1 stop
$133Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
 Logo
5:30 am - 3:58 pmCLE-MDW
11h 28m1 stop
 Logo
6:20 am - 6:24 pmMDW-CLE
11h 04m2 stops
Thu, Sep 25 - Mon, Sep 29
 Logo
10:26 am - 4:51 pmCLE-ORD
7h 25m1 stop
 Logo
11:57 am - 7:22 pmORD-CLE
30h 25m2 stops
Tue, Sep 9 - Wed, Sep 10
United Airlines Logo
7:00 am - 7:34 amCLE-ORD
1h 34mnonstop
United Airlines Logo
12:55 pm - 3:17 pmORD-CLE
1h 22mnonstop
$203United Airlines
Find Deal
Wed, Sep 24 - Wed, Oct 1
JetBlue Logo
11:00 am - 6:18 pmCLE-ORD
8h 18m1 stop
JetBlue Logo
11:20 am - 6:46 pmORD-CLE
6h 26m1 stop
$207JetBlue
Find Deal
Wed, Oct 22 - Wed, Oct 29
Southwest Logo
1:05 pm - 1:20 pmCLE-MDW
1h 15mnonstop
Southwest Logo
9:55 pm - 12:05 amMDW-CLE
1h 10mnonstop
$210Southwest
Find Deal
Tue, Oct 21 - Thu, Oct 23
United Airlines Logo
8:40 am - 9:14 amCLE-ORD
1h 34mnonstop
United Airlines Logo
10:50 am - 1:14 pmORD-CLE
1h 24mnonstop
$210United Airlines
Find Deal
Tue, Oct 21 - Thu, Oct 23
Southwest Logo
4:00 pm - 4:15 pmCLE-MDW
1h 15mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW-CLE
1h 15mnonstop
$217Southwest
Find Deal
Sat, Sep 20 - Mon, Sep 22

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets
Frontier
Sep 25
CLE7:34 pmCleveland Hopkins Intl
5h 36m
1 stop
ORD12:10 amChicago O'Hare Intl
Oct 2
ORD5:50 pmChicago O'Hare Intl
5h 53m
1 stop
CLE12:43 amCleveland Hopkins Intl
Frontier
Sep 18
CLE7:34 pmCleveland Hopkins Intl
5h 36m
1 stop
ORD12:10 amChicago O'Hare Intl
Sep 22
ORD6:21 pmChicago O'Hare Intl
17h 14m
1 stop
CLE12:35 pmCleveland Hopkins Intl
Frontier
Sep 20
CLE7:19 pmCleveland Hopkins Intl
4h 58m
1 stop
MDW11:17 pmChicago Midway
Sep 22
MDW5:15 pmChicago Midway
6h 28m
1 stop
CLE12:43 amCleveland Hopkins Intl

Delta flights from Cleveland to Chicago

Our best Delta deals on Cleveland to Chicago flight tickets
Delta
Sep 3
CLE5:30 amCleveland Hopkins Intl
3h 34m
1 stop
ORD8:04 amChicago O'Hare Intl
Sep 3
ORD2:00 pmChicago O'Hare Intl
3h 48m
1 stop
CLE6:48 pmCleveland Hopkins Intl
Delta
Sep 3
CLE6:00 amCleveland Hopkins Intl
7h 45m
2 stops
ORD12:45 pmChicago O'Hare Intl
Sep 3
ORD6:00 pmChicago O'Hare Intl
5h 40m
1 stop
CLE12:40 amCleveland Hopkins Intl
Delta
Sep 24
CLE5:30 amCleveland Hopkins Intl
4h 10m
1 stop
MDW8:40 amChicago Midway
Oct 1
MDW9:35 amChicago Midway
2h 52m
1 stop
CLE1:27 pmCleveland Hopkins Intl

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 August 28, 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 - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/25

5:30 am-3:58 pm

1 stop11h 28m

Chicago Midway

Thu 10/2

4:56 pm-12:43 am

1 stop6h 47m

$132

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 9/25

7:34 pm-12:10 am

1 stop5h 36m

Chicago O'Hare Intl

Thu 10/2

5:50 pm-12:43 am

1 stop5h 53m

$132

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/18

7:34 pm-11:20 pm

1 stop28h 46m

Chicago Midway

Mon 9/22

5:15 pm-12:43 am

1 stop6h 28m

$133

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 9/25

5:30 am-3:58 pm

1 stop11h 28m

Chicago Midway

Mon 9/29

6:20 am-6:24 pm

2 stops11h 04m

$173

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 9/9

10:26 am-4:51 pm

1 stop7h 25m

Chicago O'Hare Intl

Wed 9/10

11:57 am-7:22 pm

2 stops30h 25m

$174

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 9/24

7:00 am-7:34 am

Nonstop1h 34m

Chicago O'Hare Intl

Wed 10/1

12:55 pm-3:17 pm

Nonstop1h 22m

$203

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 10/22

11:00 am-6:18 pm

1 stop8h 18m

Chicago O'Hare Intl

Wed 10/29

11:20 am-6:46 pm

1 stop6h 26m

$207

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 10/21

1:05 pm-1:20 pm

Nonstop1h 15m

Chicago Midway

Thu 10/23

9:55 pm-12:05 am

Nonstop1h 10m

$210

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 10/21

8:40 am-9:14 am

Nonstop1h 34m

Chicago O'Hare Intl

Thu 10/23

10:50 am-1:14 pm

Nonstop1h 24m

$210

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 9/20

4:00 pm-4:15 pm

Nonstop1h 15m

Chicago Midway

Mon 9/22

8:50 pm-11:05 pm

Nonstop1h 15m

$217

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 typical price of a round-trip flight between Cleveland and Chicago?

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 $474. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $664.

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 $484. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $864.

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 $297 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?

No. A direct flight is the cheapest option for a flight between Cleveland to Chicago.

How have Cleveland to Chicago flight prices changed over time?

As of August 2025, prices for Cleveland to Chicago flights are approximately 11% cheaper 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

$178

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 $178. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $218.
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)
  • 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
3,204 reviews
Search Frontier flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $142Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
United AirlinesPriceFrom $156Free CancellationRating
7.4
8,944 reviews
Search United Airlines flights
  • Southwest Flights From Cleveland to Chicago

    Southwest flight deals from Cleveland to Chicago start from $142 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $275 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 8,944 reviews) operates around 37 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $319, with deals from around $156 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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1 adult
Tue 9/2
Tue 9/9

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