How many flights depart from Cleveland to Chicago on average per day?

The number of flights available between Cleveland and Chicago is 17 per day as of December 2025. The most frequent departure time is 2:00PM, with 47% of daily flights leaving in the afternoon.

What is the cheapest airline that flies from Cleveland Hopkins Intl to Chicago?

Frontier, Southwest, and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Chicago

What airlines fly to Chicago?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Cleveland according to our data. United Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Cleveland to Chicago on average per week?

The number of flights available between Cleveland and Chicago is 120 per week as of December 2025. The most frequent departure day is Tue, with 42% of weekly flights leaving on this day.

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?

As of December 2025, there are 4 operators available to choose from 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.

$64 Cheap Flights from Cleveland to Chicago in 2025/26

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Cheap round-trip flights

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7:10 am - 11:45 am

CLE

MDW

5h 35m1 stop

5:01 pm - 11:11 pm

MDW

CLE

29h 10m1 stop

$203Frontier

Fri, Jan 23 - Sun, Jan 25

8:20 pm - 4:19 pm

CLE

ORD

20h 59m2 stops

7:21 pm - 2:43 pm

ORD

CLE

18h 22m1 stop

$203Multiple Airlines

Tue, Jan 6 - Fri, Jan 9

8:49 am - 9:31 am

CLE

ORD

1h 42mnonstop

7:10 am - 9:42 am

ORD

CLE

1h 32mnonstop

$204United Airlines

Thu, Jan 15 - Sun, Jan 18

6:35 am - 7:10 am

CLE

MDW

1h 35mnonstop

7:55 pm - 10:10 pm

MDW

CLE

1h 15mnonstop

$204Southwest

Thu, Jan 15 - Sun, Jan 18

12:55 pm - 9:05 pm

CLE

ORD

9h 10m2 stops

6:15 am - 1:16 pm

ORD

CLE

6h 01m2 stops

$207Delta

Sat, Jan 17 - Sun, Jan 18

8:08 am - 8:59 am

CLE

ORD

1h 51mnonstop

11:11 am - 1:40 pm

ORD

CLE

1h 29mnonstop

$208American Airlines

Sat, Jan 17 - Sun, Jan 18

11:43 am - 10:17 pm

CLE

MDW

11h 34m2 stops

12:50 pm - 12:32 am

MDW

CLE

10h 42m1 stop

$210Multiple Airlines

Tue, Jan 6 - Thu, Jan 8

11:00 am - 11:47 am

CLE

ORD

1h 47mnonstop

8:08 am - 10:38 am

ORD

CLE

1h 30mnonstop

$211American Airlines

Tue, Jan 6 - Wed, Jan 7

3:45 pm - 7:00 pm

CLE

MDW

4h 15m1 stop

3:00 pm - 5:10 pm

MDW

CLE

1h 10mnonstop

$214Southwest

Sat, Jan 17 - Sun, Jan 18

12:29 pm - 6:36 pm

CLE

MDW

7h 07m1 stop

9:33 am - 1:57 pm

MDW

CLE

3h 24m1 stop

$224Delta

Tue, Jan 20 - Sat, Jan 24

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets

American Airlines

Dec 24

CLE5:33 amCleveland Hopkins Intl

1h 47m

ORD6:20 amChicago O'Hare Intl

Dec 24

ORD12:16 pmChicago O'Hare Intl

1h 28m

CLE2:44 pmCleveland Hopkins Intl

$207

Find similar

American Airlines

Jan 17

CLE8:08 amCleveland Hopkins Intl

1h 51m

ORD8:59 amChicago O'Hare Intl

Jan 18

ORD11:11 amChicago O'Hare Intl

1h 29m

CLE1:40 pmCleveland Hopkins Intl

$208

Find similar

American Airlines

Jan 6

CLE11:00 amCleveland Hopkins Intl

1h 47m

ORD11:47 amChicago O'Hare Intl

Jan 7

ORD8:08 amChicago O'Hare Intl

1h 30m

CLE10:38 amCleveland Hopkins Intl

$211

Find similar

Delta flights from Cleveland to Chicago

Our best Delta deals on Cleveland to Chicago flight tickets

Delta

Jan 17

CLE6:00 amCleveland Hopkins Intl

7h 48m

2 stops

MDW12:48 pmChicago Midway

Jan 18

MDW5:59 pmChicago Midway

5h 37m

1 stop

CLE12:36 amCleveland Hopkins Intl

$202

Find similar

Delta

Jan 17

CLE12:55 pmCleveland Hopkins Intl

9h 10m

2 stops

ORD9:05 pmChicago O'Hare Intl

Jan 18

ORD6:15 amChicago O'Hare Intl

6h 01m

2 stops

CLE1:16 pmCleveland Hopkins Intl

$207

Find similar

Delta

Jan 20

CLE12:29 pmCleveland Hopkins Intl

7h 07m

1 stop

MDW6:36 pmChicago Midway

Jan 24

MDW9:33 amChicago Midway

3h 24m

1 stop

CLE1:57 pmCleveland Hopkins Intl

$224

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 1/23

7:10 am-11:45 am

1 stop5h 35m

Chicago Midway

Sun 1/25

5:01 pm-11:11 pm

1 stop29h 10m

$203

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 1/6

8:20 pm-4:19 pm

2 stops20h 59m

Chicago O'Hare Intl

Fri 1/9

7:21 pm-2:43 pm

1 stop18h 22m

$203

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 1/15

8:49 am-9:31 am

Nonstop1h 42m

Chicago O'Hare Intl

Sun 1/18

7:10 am-9:42 am

Nonstop1h 32m

$204

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 1/15

6:35 am-7:10 am

Nonstop1h 35m

Chicago Midway

Sun 1/18

7:55 pm-10:10 pm

Nonstop1h 15m

$204

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 1/17

12:55 pm-9:05 pm

2 stops9h 10m

Chicago O'Hare Intl

Sun 1/18

6:15 am-1:16 pm

2 stops6h 01m

$207

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 1/17

8:08 am-8:59 am

Nonstop1h 51m

Chicago O'Hare Intl

Sun 1/18

11:11 am-1:40 pm

Nonstop1h 29m

$208

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/6

11:43 am-10:17 pm

2 stops11h 34m

Chicago Midway

Thu 1/8

12:50 pm-12:32 am

1 stop10h 42m

$210

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 1/6

11:00 am-11:47 am

Nonstop1h 47m

Chicago O'Hare Intl

Wed 1/7

8:08 am-10:38 am

Nonstop1h 30m

$211

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 1/17

3:45 pm-7:00 pm

1 stop4h 15m

Chicago Midway

Sun 1/18

3:00 pm-5:10 pm

Nonstop1h 10m

$214

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/20

12:29 pm-6:36 pm

1 stop7h 07m

Chicago Midway

Sat 1/24

9:33 am-1:57 pm

1 stop3h 24m

$224

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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

Prices

Airlines

Other information

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 $248.

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 $467. 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 $686.

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 $478. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $850.

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

Fly from Cleveland Hopkins Intl to Chicago O'Hare Intl 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 $292 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 $88 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 25% 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 December 2025, prices for Cleveland to Chicago flights are approximately 29% 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	$183
Fastest flight time	1h 20m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Cleveland in the past 72 hours is $183. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $346.

The fastest flight from Cleveland to Chicago takes 1h 20m

Direct flights go from Cleveland to Chicago every day.

There are 3 airports in Chicago. From Cleveland there are direct flights to 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 20m.
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?
As of December 2025, there are 4 operators available to choose from 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?
momondo data reveals that the most frequently booked plane model on the route from Cleveland to Chicago is Boeing 737-700, representing 9.82% of all bookings. The subsequent popular models are Boeing 737-800 at 9.51%, Boeing 737 MAX 8 at 8.30%, and Canadair (Bombardier) Regional Jet 700 at 8.17%.
What is the most popular airline from Cleveland to Chicago?
momondo data reveals that the most frequently booked airline on the route from Cleveland to Chicago is United Airlines, representing 38% of all bookings. The subsequent popular airlines are Southwest at 35%, American Airlines at 23%, and Frontier at 4%.

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
American Airlines	PriceFrom $133	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
Southwest	PriceFrom $140	Free Cancellation	Rating 7.9 4,250 reviews	Search Southwest flights
Frontier	PriceFrom $143	Free Cancellation	Rating 5.8 3,082 reviews	Search Frontier flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 9,094 reviews	Search United Airlines flights

Southwest Flights From Cleveland to Chicago
Southwest flight deals from Cleveland to Chicago start from $140 round-trip. Over the 9 Southwest flights for this route in a normal week, average airfare is usually $272 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 9,094 reviews) operates around 17 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $299, 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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Cheap flights from Cleveland to Chicago from $64

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 1/21. 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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Big names and deals

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American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets

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Our best Delta deals on Cleveland to Chicago flight tickets

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Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Cleveland to 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 $248.

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

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 $478. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $850.

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

Fly from Cleveland Hopkins Intl to Chicago O'Hare Intl for the best Cleveland Hopkins Intl - Chicago flight prices

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

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 25% 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 December 2025, prices for Cleveland to Chicago flights are approximately 29% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Cleveland Hopkins Intl to Chicago?

Frontier, Southwest, and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Chicago

What airlines fly to Chicago?

How many flights depart from Cleveland to Chicago on average per day?

The number of flights available between Cleveland and Chicago is 17 per day as of December 2025. The most frequent departure time is 2:00PM, with 47% of daily flights leaving in the afternoon.

How many flights depart from Cleveland to Chicago on average per week?

The number of flights available between Cleveland and Chicago is 120 per week as of December 2025. The most frequent departure day is Tue, with 42% of weekly flights leaving on this day.

When to book flights from Cleveland to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

How far is Cleveland Hopkins Intl to Chicago by plane?

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

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?

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

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

Southwest Flights From Cleveland to Chicago

United Airlines Flights From Cleveland to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

How can momondo help me find flights from Cleveland to Chicago?

I’m not ready to book a flight from Cleveland to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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