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 286 per week as of January 2026. The most frequent departure day is Thu, with 19% of weekly flights leaving on this day.

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

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

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

The number of flights available between Cleveland and Chicago is 40 per day as of January 2026. The most frequent departure time is 10:00AM, with 39% of daily flights leaving at noon.

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 January 2026, 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 2026

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

9:00 am - 4:35 pm

CLE

ORD

8h 35m1 stop

12:21 pm - 12:43 am

ORD

CLE

11h 22m1 stop

$180Frontier

Sat, Jan 24 - Sun, Jan 25

7:21 pm - 11:22 am

CLE

ORD

17h 01m1 stop

4:38 pm - 7:34 am

ORD

CLE

13h 56m2 stops

$181Multiple Airlines

Fri, Feb 6 - Sat, Feb 7

7:10 am - 1:37 pm

CLE

ORD

7h 27m1 stop

10:00 am - 7:29 pm

ORD

CLE

8h 29m1 stop

$183Multiple Airlines

Thu, Feb 5 - Thu, Feb 12

9:00 am - 9:15 am

CLE

MDW

1h 15mnonstop

7:00 pm - 9:15 pm

MDW

CLE

1h 15mnonstop

$185Southwest

Tue, Apr 7 - Thu, Apr 9

3:44 pm - 11:47 pm

CLE

ORD

9h 03m1 stop

5:40 am - 11:11 pm

ORD

CLE

16h 31m1 stop

$185Multiple Airlines

Fri, Feb 6 - Mon, Feb 9

4:16 pm - 5:02 pm

CLE

ORD

1h 46mnonstop

7:30 am - 9:48 am

ORD

CLE

1h 18mnonstop

$187United Airlines

Sat, Feb 28 - Mon, Mar 2

6:30 am - 8:53 am

CLE

MDW

3h 23m1 stop

10:45 am - 7:02 pm

MDW

CLE

7h 17m1 stop

$187Delta

Fri, Mar 13 - Mon, Mar 16

2:30 pm - 2:50 pm

CLE

MDW

1h 20mnonstop

6:00 pm - 8:10 pm

MDW

CLE

1h 10mnonstop

$189Southwest

Mon, Mar 9 - Wed, Mar 11

7:32 pm - 8:19 pm

CLE

ORD

1h 47mnonstop

9:11 pm - 11:35 pm

ORD

CLE

1h 24mnonstop

$190American Airlines

Thu, Jan 29 - Mon, Feb 2

5:00 am - 5:36 am

CLE

ORD

1h 36mnonstop

6:57 am - 9:21 am

ORD

CLE

1h 24mnonstop

$191American Airlines

Fri, Mar 20 - Sat, Mar 21

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets

Frontier

Jan 24

CLE9:00 amCleveland Hopkins Intl

8h 35m

1 stop

ORD4:35 pmChicago O'Hare Intl

Jan 25

ORD12:21 pmChicago O'Hare Intl

11h 22m

1 stop

CLE12:43 amCleveland Hopkins Intl

$180

Frontier

Feb 15

CLE1:20 pmCleveland Hopkins Intl

12h 00m

1 stop

ORD12:20 amChicago O'Hare Intl

Feb 21

ORD4:42 pmChicago O'Hare Intl

13h 52m

1 stop

CLE7:34 amCleveland Hopkins Intl

$181

Frontier

Jan 25

CLE7:10 amCleveland Hopkins Intl

7h 27m

1 stop

ORD1:37 pmChicago O'Hare Intl

Jan 29

ORD5:40 amChicago O'Hare Intl

12h 09m

2 stops

CLE6:49 pmCleveland Hopkins Intl

$186

Delta flights from Cleveland to Chicago

Our best Delta deals on Cleveland to Chicago flight tickets

Delta

Mar 13

CLE4:41 pmCleveland Hopkins Intl

6h 50m

1 stop

MDW10:31 pmChicago Midway

Mar 16

MDW12:47 pmChicago Midway

5h 15m

1 stop

CLE7:02 pmCleveland Hopkins Intl

$187

Delta

Mar 13

CLE6:00 amCleveland Hopkins Intl

8h 17m

2 stops

ORD1:17 pmChicago O'Hare Intl

Mar 16

ORD6:00 amChicago O'Hare Intl

4h 15m

1 stop

CLE11:15 amCleveland Hopkins Intl

$192

Delta

Mar 13

CLE6:00 amCleveland Hopkins Intl

7h 29m

2 stops

MDW12:29 pmChicago Midway

Mar 16

MDW1:10 pmChicago Midway

10h 21m

2 stops

CLE12:31 amCleveland Hopkins Intl

$198

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 1/24

9:00 am-4:35 pm

1 stop8h 35m

Chicago O'Hare Intl

Sun 1/25

12:21 pm-12:43 am

1 stop11h 22m

$180

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 2/6

7:21 pm-11:22 am

1 stop17h 01m

Chicago O'Hare Intl

Sat 2/7

4:38 pm-7:34 am

2 stops13h 56m

$181

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 2/5

7:10 am-1:37 pm

1 stop7h 27m

Chicago O'Hare Intl

Thu 2/12

10:00 am-7:29 pm

1 stop8h 29m

$183

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 4/7

9:00 am-9:15 am

Nonstop1h 15m

Chicago Midway

Thu 4/9

7:00 pm-9:15 pm

Nonstop1h 15m

$185

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 2/6

3:44 pm-11:47 pm

1 stop9h 03m

Chicago O'Hare Intl

Mon 2/9

5:40 am-11:11 pm

1 stop16h 31m

$185

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 2/28

4:16 pm-5:02 pm

Nonstop1h 46m

Chicago O'Hare Intl

Mon 3/2

7:30 am-9:48 am

Nonstop1h 18m

$187

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 3/13

6:30 am-8:53 am

1 stop3h 23m

Chicago Midway

Mon 3/16

10:45 am-7:02 pm

1 stop7h 17m

$187

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 3/9

2:30 pm-2:50 pm

Nonstop1h 20m

Chicago Midway

Wed 3/11

6:00 pm-8:10 pm

Nonstop1h 10m

$189

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 1/29

7:32 pm-8:19 pm

Nonstop1h 47m

Chicago O'Hare Intl

Mon 2/2

9:11 pm-11:35 pm

Nonstop1h 24m

$190

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 3/20

5:00 am-5:36 am

Nonstop1h 36m

Chicago O'Hare Intl

Sat 3/21

6:57 am-9:21 am

Nonstop1h 24m

$191

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 $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 $462. 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 $681.

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 $471. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $838.

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 $285 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 12% 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 January 2026, prices for Cleveland to Chicago flights are approximately 1% 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	$170
Fastest flight time	1h 15m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Cleveland in the past 72 hours is $170. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $308.

The fastest flight from Cleveland to Chicago takes 1h 15m

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 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 January 2026, 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 737-800, representing 9.91% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 9.28%, Boeing 737-700 at 9.06%, and Embraer 175 (Enhanced Winglets) at 8.65%.
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 39% of all bookings. The subsequent popular airlines are Southwest at 35%, American Airlines at 21%, 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 $133	Free Cancellation	Rating 7.2 11,095 reviews	Search American Airlines flights
Southwest	PriceFrom $140	Free Cancellation	Rating 8.0 4,250 reviews	Search Southwest flights
Frontier	PriceFrom $143	Free Cancellation	Rating 5.7 3,061 reviews	Search Frontier flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 9,141 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 10 Southwest flights for this route in a normal week, average airfare is usually $270 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 9,139 reviews) operates around 30 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $295, 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

Munster

Crown Point

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 2/3. 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

Filter for what you want

Filter for what you want

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Frontier flights from Cleveland to Chicago

Our best Frontier 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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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 $242.

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 $471. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $838.

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 12% 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 January 2026, prices for Cleveland to Chicago flights are approximately 1% cheaper when compared to flights at the same time last year.

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

Southwest and United Airlines 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 40 per day as of January 2026. The most frequent departure time is 10:00AM, with 39% of daily flights leaving at noon.

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

The number of flights available between Cleveland and Chicago is 286 per week as of January 2026. The most frequent departure day is Thu, with 19% 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