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 53% 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.

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

Frontier, Delta, and Southwest 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 41 per day as of April 2026. The most frequent departure time is 11:00AM, with 47% 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 290 per week as of April 2026. The most frequent departure day is Thu, with 23% 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 April 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.

$78 Cheap Flights from Cleveland to Chicago in 2026

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Round-trip

One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

3:33 pm - 10:14 pm

CLE

MDW

7h 41m

1 stop

6:10 am - 2:26 pm

MDW

CLE

7h 16m

1 stop

$140Frontier

Tue, Apr 28 - Wed, Apr 29

4:28 pm - 11:06 pm

CLE

ORD

7h 38m

1 stop

5:50 am - 2:49 pm

ORD

CLE

7h 59m

1 stop

$140Frontier

Mon, Apr 20 - Thu, Apr 23

10:00 pm - 5:54 pm

CLE

MDW

20h 54m

1 stop

6:20 am - 5:49 pm

MDW

CLE

10h 29m

1 stop

$141Frontier

Thu, Apr 23 - Mon, Apr 27

11:51 am - 10:39 pm

CLE

ORD

11h 48m

1 stop

9:42 pm - 10:57 am

ORD

CLE

12h 15m

1 stop

$141Frontier

Sat, May 2 - Tue, May 5

10:30 am - 3:50 pm

CLE

MDW

6h 20m

2 stops

9:50 am - 5:00 pm

MDW

CLE

6h 10m

1 stop

$142Southwest

Wed, May 6 - Wed, May 20

8:41 pm - 9:24 pm

CLE

ORD

1h 43mnonstop

7:34 pm - 10:02 pm

ORD

CLE

1h 28mnonstop

$142American Airlines

Wed, May 27 - Tue, Jun 2

4:22 pm - 10:23 am

CLE

ORD

19h 01m

1 stop

5:50 am - 2:49 pm

ORD

CLE

7h 59m

1 stop

$143Multiple Airlines

Mon, Apr 20 - Thu, Apr 30

4:22 pm - 10:23 am

CLE

ORD

19h 01m

1 stop

11:28 am - 7:44 am

ORD

CLE

19h 16m

1 stop

$145Multiple Airlines

Mon, Apr 27 - Wed, Apr 29

10:30 am - 3:50 pm

CLE

MDW

6h 20m

2 stops

7:50 am - 5:25 pm

MDW

CLE

8h 35m

2 stops

$147Southwest

Wed, Apr 29 - Wed, May 6

1:44 pm - 5:56 pm

CLE

MDW

5h 12m

1 stop

5:15 pm - 11:03 pm

MDW

CLE

4h 48m

1 stop

$157Delta

Wed, May 27 - Tue, Jun 2

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets

Frontier

Apr 20

CLE4:28 pmCleveland Hopkins Intl

7h 38m

1 stop

ORD11:06 pmChicago O'Hare Intl

Apr 23

ORD5:50 amChicago O'Hare Intl

7h 59m

1 stop

CLE2:49 pmCleveland Hopkins Intl

$140

Frontier

May 2

CLE11:51 amCleveland Hopkins Intl

11h 48m

1 stop

ORD10:39 pmChicago O'Hare Intl

May 5

ORD9:42 pmChicago O'Hare Intl

12h 15m

1 stop

CLE10:57 amCleveland Hopkins Intl

$141

Frontier

Apr 29

CLE3:33 pmCleveland Hopkins Intl

7h 41m

1 stop

MDW10:14 pmChicago Midway

May 1

MDW2:15 pmChicago Midway

19h 28m

1 stop

CLE10:43 amCleveland Hopkins Intl

$146

Delta flights from Cleveland to Chicago

Our best Delta deals on Cleveland to Chicago flight tickets

Delta

May 6

CLE4:00 pmCleveland Hopkins Intl

5h 40m

1 stop

ORD8:40 pmChicago O'Hare Intl

May 20

ORD7:00 amChicago O'Hare Intl

5h 23m

1 stop

CLE1:23 pmCleveland Hopkins Intl

$157

Delta

May 27

CLE4:00 pmCleveland Hopkins Intl

3h 33m

1 stop

MDW6:33 pmChicago Midway

Jun 2

MDW9:22 amChicago Midway

8h 09m

2 stops

CLE6:31 pmCleveland Hopkins Intl

$162

Delta

May 6

CLE12:00 pmCleveland Hopkins Intl

6h 58m

2 stops

MDW5:58 pmChicago Midway

May 20

MDW1:22 pmChicago Midway

8h 41m

2 stops

CLE11:03 pmCleveland Hopkins Intl

$167

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 4/28

3:33 pm-10:14 pm

1 stop7h 41m

Chicago Midway

Wed 4/29

6:10 am-2:26 pm

1 stop7h 16m

$140

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 4/20

4:28 pm-11:06 pm

1 stop7h 38m

Chicago O'Hare Intl

Thu 4/23

5:50 am-2:49 pm

1 stop7h 59m

$140

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 4/23

10:00 pm-5:54 pm

1 stop20h 54m

Chicago Midway

Mon 4/27

6:20 am-5:49 pm

1 stop10h 29m

$141

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 5/2

11:51 am-10:39 pm

1 stop11h 48m

Chicago O'Hare Intl

Tue 5/5

9:42 pm-10:57 am

1 stop12h 15m

$141

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 5/6

10:30 am-3:50 pm

2 stops6h 20m

Chicago Midway

Wed 5/20

9:50 am-5:00 pm

1 stop6h 10m

$142

Quickest round-trip

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 5/27

8:41 pm-9:24 pm

Nonstop1h 43m

Chicago O'Hare Intl

Tue 6/2

7:34 pm-10:02 pm

Nonstop1h 28m

$142

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 4/20

4:22 pm-10:23 am

1 stop19h 01m

Chicago O'Hare Intl

Thu 4/30

5:50 am-2:49 pm

1 stop7h 59m

$143

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 4/27

4:22 pm-10:23 am

1 stop19h 01m

Chicago O'Hare Intl

Wed 4/29

11:28 am-7:44 am

1 stop19h 16m

$145

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 4/29

10:30 am-3:50 pm

2 stops6h 20m

Chicago Midway

Wed 5/6

7:50 am-5:25 pm

2 stops8h 35m

$147

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 5/27

1:44 pm-5:56 pm

1 stop5h 12m

Chicago Midway

Tue 6/2

5:15 pm-11:03 pm

1 stop4h 48m

$157

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 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 $241.

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 $448. 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 $635.

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 $451. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $796.

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 $304 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?

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 April 2026, prices for Cleveland to Chicago flights are approximately 28% 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	$199
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 $199. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $355.

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).

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Frequently asked questions about flying from Cleveland to Chicago

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 April 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 14.01% of all bookings. The subsequent popular models are Airbus A319 at 12.24%, Boeing 737 MAX 8 at 10.33%, and Embraer 175 (Enhanced Winglets) at 8.84%.
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 44% of all bookings. The subsequent popular airlines are Southwest at 28%, 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 $127	Free Cancellation	Rating 7.1 11,552 reviews	Search American Airlines flights
Southwest	PriceFrom $139	Free Cancellation	Rating 8.0 4,337 reviews	Search Southwest flights
Frontier	PriceFrom $143	Free Cancellation	Rating 5.7 3,003 reviews	Search Frontier flights
United Airlines	PriceFrom $144	Free Cancellation	Rating 7.4 9,533 reviews	Search United Airlines flights

Southwest Flights From Cleveland to Chicago
Southwest flight deals from Cleveland to Chicago start from $139 round-trip. Over the 9 Southwest flights for this route in a normal week, average airfare is usually $262 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 9,533 reviews) operates around 31 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $297, with deals from around $144 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

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Schererville

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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Cheap flights from Cleveland to Chicago from $78

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 5/4. 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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How to get the cheapest flight ticket from Cleveland to Chicago

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

What is the cheapest month to fly to Chicago?

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?

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

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

What cabin class options are available on Cleveland Hopkins Intl to Chicago flights?

Can stopping save me money on Cleveland to Chicago flights?

How have Cleveland to Chicago flight prices changed over time?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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