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

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

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

The number of flights available between Cleveland and Chicago is 365 per week as of December 2025. The most frequent departure day is Fri, with 18% of weekly flights leaving on this day.

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

The number of flights available between Cleveland and Chicago is 52 per day as of December 2025. The most frequent departure time is 2:00PM, with 41% of daily flights leaving in the afternoon.

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.

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.

$56 Cheap Flights from Cleveland to Chicago in 2025/26

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7:10 am - 11:35 pm

CLE

ORD

17h 25m1 stop

5:40 am - 1:28 pm

ORD

CLE

6h 48m1 stop

$226Frontier

sáb., feb. 14 - dom., feb. 15

6:55 am - 7:30 am

CLE

MDW

1h 35mnonstop

2:35 pm - 8:50 pm

MDW

CLE

5h 15m1 stop

$227Southwest

sáb., ene. 17 - dom., ene. 18

6:00 am - 6:49 am

CLE

ORD

1h 49mnonstop

6:40 am - 12:24 pm

ORD

CLE

4h 44m1 stop

$227American Airlines

sáb., feb. 14 - dom., feb. 15

4:07 pm - 4:57 pm

CLE

ORD

1h 50mnonstop

6:11 pm - 8:40 pm

ORD

CLE

1h 29mnonstop

$228United Airlines

vie., ene. 9 - lun., ene. 12

6:00 am - 7:09 pm

CLE

MDW

14h 09m1 stop

6:10 am - 11:11 pm

MDW

CLE

16h 01m1 stop

$228Frontier

jue., ene. 15 - vie., ene. 16

9:30 am - 5:43 pm

CLE

ORD

9h 13m1 stop

7:45 am - 8:40 pm

ORD

CLE

11h 55m1 stop

$229JetBlue

mié., ene. 28 - vie., feb. 6

7:20 am - 8:02 am

CLE

ORD

1h 42mnonstop

7:45 pm - 10:14 pm

ORD

CLE

1h 29mnonstop

$231United Airlines

mar., ene. 6 - mar., ene. 13

6:15 am - 6:55 am

CLE

MDW

1h 40mnonstop

3:00 pm - 5:10 pm

MDW

CLE

1h 10mnonstop

$231Southwest

mar., ene. 6 - mar., ene. 13

12:18 pm - 7:45 pm

CLE

ORD

8h 27m1 stop

11:42 am - 5:20 pm

ORD

CLE

28h 38m1 stop

$235Multiple Airlines

vie., feb. 20 - dom., feb. 22

7:15 pm - 8:43 am

CLE

RFD

14h 28m1 stop

7:54 pm - 7:43 am

RFD

CLE

10h 49m1 stop

$318Multiple Airlines

jue., dic. 18 - mar., dic. 23

United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets

United Airlines

Jan 9

CLE4:07 pmCleveland Hopkins Intl

1h 50m

ORD4:57 pmChicago O'Hare Intl

Jan 12

ORD6:11 pmChicago O'Hare Intl

1h 29m

CLE8:40 pmCleveland Hopkins Intl

$228

Find similar

United Airlines

Jan 6

CLE7:20 amCleveland Hopkins Intl

1h 42m

ORD8:02 amChicago O'Hare Intl

Jan 13

ORD7:45 pmChicago O'Hare Intl

1h 29m

CLE10:14 pmCleveland Hopkins Intl

$231

Find similar

United Airlines

Jan 10

CLE7:23 amCleveland Hopkins Intl

1h 42m

ORD8:05 amChicago O'Hare Intl

Jan 12

ORD2:30 pmChicago O'Hare Intl

1h 21m

CLE4:51 pmCleveland Hopkins Intl

$234

Find similar

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets

American Airlines

Feb 14

CLE6:00 amCleveland Hopkins Intl

1h 49m

ORD6:49 amChicago O'Hare Intl

Feb 15

ORD6:40 amChicago O'Hare Intl

4h 44m

1 stop

CLE12:24 pmCleveland Hopkins Intl

$227

Find similar

American Airlines

Jan 6

CLE6:00 amCleveland Hopkins Intl

6h 35m

1 stop

ORD11:35 amChicago O'Hare Intl

Jan 7

ORD9:11 pmChicago O'Hare Intl

1h 24m

CLE11:35 pmCleveland Hopkins Intl

$241

Find similar

American Airlines

Jan 14

CLE11:00 amCleveland Hopkins Intl

1h 47m

ORD11:47 amChicago O'Hare Intl

Jan 16

ORD5:26 pmChicago O'Hare Intl

4h 33m

1 stop

CLE10:59 pmCleveland Hopkins Intl

$254

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

sáb. 2/14

7:10 am-11:35 pm

1 stop17h 25m

Chicago O'Hare Intl

dom. 2/15

5:40 am-1:28 pm

1 stop6h 48m

$226

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

sáb. 1/17

6:55 am-7:30 am

Nonstop1h 35m

Chicago Midway

dom. 1/18

2:35 pm-8:50 pm

1 stop5h 15m

$227

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

sáb. 2/14

6:00 am-6:49 am

Nonstop1h 49m

Chicago O'Hare Intl

dom. 2/15

6:40 am-12:24 pm

1 stop4h 44m

$227

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

vie. 1/9

4:07 pm-4:57 pm

Nonstop1h 50m

Chicago O'Hare Intl

lun. 1/12

6:11 pm-8:40 pm

Nonstop1h 29m

$228

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

jue. 1/15

6:00 am-7:09 pm

1 stop14h 09m

Chicago Midway

vie. 1/16

6:10 am-11:11 pm

1 stop16h 01m

$228

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

mié. 1/28

9:30 am-5:43 pm

1 stop9h 13m

Chicago O'Hare Intl

vie. 2/6

7:45 am-8:40 pm

1 stop11h 55m

$229

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

mar. 1/6

7:20 am-8:02 am

Nonstop1h 42m

Chicago O'Hare Intl

mar. 1/13

7:45 pm-10:14 pm

Nonstop1h 29m

$231

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

mar. 1/6

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

mar. 1/13

3:00 pm-5:10 pm

Nonstop1h 10m

$231

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

vie. 2/20

12:18 pm-7:45 pm

1 stop8h 27m

Chicago O'Hare Intl

dom. 2/22

11:42 am-5:20 pm

1 stop28h 38m

$235

ClevelandChicago

CLE - RFD

CLERFD

Cleveland Hopkins Intl

jue. 12/18

7:15 pm-8:43 am

1 stop14h 28m

Chicago Greater Rockford

mar. 12/23

7:54 pm-7:43 am

1 stop10h 49m

$318

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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 $464. 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 $690.

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 $479. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $858.

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 $293 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 30% 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 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 $183. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $358.

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?
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 9.87% of all bookings. The subsequent popular models are Boeing 737-800 at 9.54%, Boeing 737 MAX 8 at 8.60%, and Canadair (Bombardier) Regional Jet 700 at 7.95%.
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 37% of all bookings. The subsequent popular airlines are Southwest at 35%, American Airlines at 23%, and Frontier at 5%.

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 $136	Free Cancellation	Rating 7.2 11,044 reviews	Search American Airlines flights
Southwest	PriceFrom $140	Free Cancellation	Rating 8.0 4,252 reviews	Search Southwest flights
Frontier	PriceFrom $143	Free Cancellation	Rating 5.8 3,087 reviews	Search Frontier flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 9,078 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 23 Southwest flights for this route in a normal week, average airfare is usually $273 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 9,078 reviews) operates around 49 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $298, 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

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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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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United Airlines flights from Cleveland to Chicago

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American Airlines flights from Cleveland to Chicago

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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

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 $479. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $858.

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 30% 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?

Southwest, United Airlines, 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 52 per day as of December 2025. The most frequent departure time is 2:00PM, with 41% 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 365 per week as of December 2025. The most frequent departure day is Fri, with 18% 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