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

Southwest, United Airlines, and Frontier 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 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 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 day?

The number of flights available between Cleveland and Chicago is 59 per day as of July 2025. The most frequent departure time is 11:00AM, with 48% 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 419 per week as of July 2025. The most frequent departure day is Mon, with 18% 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 July 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

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

10:55 am - 11:10 amCLE-MDW

1h 15mnonstop

1:00 pm - 3:15 pmMDW-CLE

1h 15mnonstop

$127Southwest

Find Deal

Thu, Aug 7 - Mon, Aug 11

6:00 pm - 6:35 pmCLE-ORD

1h 35mnonstop

7:10 am - 9:36 amORD-CLE

1h 26mnonstop

$127United Airlines

Find Deal

Sat, Aug 9 - Sat, Aug 16

8:53 pm - 9:30 pmCLE-ORD

1h 37mnonstop

7:10 am - 9:39 amORD-CLE

1h 29mnonstop

$128American Airlines

Find Deal

Thu, Aug 7 - Sat, Aug 9

7:15 am - 7:30 amCLE-MDW

1h 15mnonstop

2:05 pm - 9:20 pmMDW-CLE

6h 15m1 stop

$137Southwest

Find Deal

Sat, Sep 20 - Wed, Sep 24

2:11 pm - 2:49 pmCLE-ORD

1h 38mnonstop

12:54 pm - 3:21 pmORD-CLE

1h 27mnonstop

$138American Airlines

Find Deal

Thu, Aug 21 - Sun, Aug 24

6:00 am - 6:27 amCLE-ORD

1h 27mnonstop

7:30 am - 9:56 amORD-CLE

1h 26mnonstop

$151United Airlines

Find Deal

Sun, Aug 10 - Sun, Aug 17

6:00 am - 12:20 pmCLE-ORD

7h 20m1 stop

7:00 am - 4:23 pmORD-CLE

8h 23m1 stop

$169Frontier

Find Deal

Thu, Aug 21 - Sat, Aug 23

5:30 am - 10:16 amCLE-ORD

5h 46m1 stop

7:00 pm - 11:53 pmORD-CLE

3h 53m1 stop

$176Delta

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Thu, Aug 7 - Mon, Aug 11

5:30 am - 8:44 amCLE-MDW

4h 14m1 stop

9:31 am - 1:32 pmMDW-CLE

3h 01m1 stop

$177Delta

Find Deal

Sun, Aug 10 - Tue, Aug 12

5:30 am - 10:28 amCLE-ORD

5h 58m1 stop

6:16 pm - 12:43 amORD-CLE

5h 27m1 stop

$188Frontier

Find Deal

Thu, Sep 25 - Thu, Sep 25

United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets

United Airlines

Aug 9

CLE6:00 pmCleveland Hopkins Intl

1h 35m

ORD6:35 pmChicago O'Hare Intl

Aug 16

ORD7:10 amChicago O'Hare Intl

1h 26m

CLE9:36 amCleveland Hopkins Intl

$127

Find similar

United Airlines

Aug 10

CLE6:00 amCleveland Hopkins Intl

1h 27m

ORD6:27 amChicago O'Hare Intl

Aug 17

ORD7:30 amChicago O'Hare Intl

1h 26m

CLE9:56 amCleveland Hopkins Intl

$151

Find similar

United Airlines

Sep 25

CLE7:37 pmCleveland Hopkins Intl

1h 34m

ORD8:11 pmChicago O'Hare Intl

Oct 2

ORD12:55 pmChicago O'Hare Intl

1h 22m

CLE3:17 pmCleveland Hopkins Intl

$187

Find similar

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets

American Airlines

Aug 7

CLE8:53 pmCleveland Hopkins Intl

1h 37m

ORD9:30 pmChicago O'Hare Intl

Aug 9

ORD7:10 amChicago O'Hare Intl

1h 29m

CLE9:39 amCleveland Hopkins Intl

$128

Find similar

American Airlines

Aug 21

CLE2:11 pmCleveland Hopkins Intl

1h 38m

ORD2:49 pmChicago O'Hare Intl

Aug 24

ORD12:54 pmChicago O'Hare Intl

1h 27m

CLE3:21 pmCleveland Hopkins Intl

$138

Find similar

American Airlines

Aug 10

CLE5:00 amCleveland Hopkins Intl

1h 37m

ORD5:37 amChicago O'Hare Intl

Aug 13

ORD3:44 pmChicago O'Hare Intl

1h 27m

CLE6:11 pmCleveland Hopkins Intl

$139

Find similar

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 $219. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Cleveland to Chicago during September average around $237.

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 $477. 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 $660.

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 $482. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $881.

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 $300 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 9% 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 July 2025, prices for Cleveland to Chicago flights are approximately 11% 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	$64
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 $64. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $127.

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)

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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 July 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 737-800, representing 11.20% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 10.71%, Boeing 737-700 at 9.89%, and Boeing 737-900 at 9.39%.
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 34% of all bookings. The subsequent popular airlines are Southwest at 33%, American Airlines at 28%, 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
Frontier	PriceFrom $100	Free Cancellation	Rating 5.9 3,260 reviews	Search Frontier flights
Southwest	PriceFrom $151	Free Cancellation	Rating 8.0 4,243 reviews	Search Southwest flights
United Airlines	PriceFrom $157	Free Cancellation	Rating 7.4 8,856 reviews	Search United Airlines flights
American Airlines	PriceFrom $157	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Southwest Flights From Cleveland to Chicago
Southwest flight deals from Cleveland to Chicago start from $151 round-trip. Over the 18 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 8,858 reviews) operates around 44 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $312, 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

Monticello

Chesterton

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 $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 8/23. 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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Find the cheapest flights from Cleveland to Chicago

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United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets

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 $219. If you’re not able to fly to Chicago in August, then September is your next best option. Flight prices from Cleveland to Chicago during September average around $237.

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 $482. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $881.

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?

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 9% 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 July 2025, prices for Cleveland to Chicago flights are approximately 11% 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 Frontier 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 59 per day as of July 2025. The most frequent departure time is 11:00AM, with 48% 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 419 per week as of July 2025. The most frequent departure day is Mon, 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