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 55% 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?

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 day?

The number of flights available between Cleveland and Chicago is 57 per day as of June 2026. The most frequent departure time is 2:00PM, with 34% 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 403 per week as of June 2026. The most frequent departure day is Mon, with 17% 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 June 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.

$98 Cheap Flights from Cleveland to Chicago in 2026

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

Prices are currently low for flights on this route. Typical prices usually range from $340 to $197. The lowest price recently found on this route was $167.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Cleveland to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:15 pm - 9:50 pm

CLE

MDW

9h 35m

2 stops

7:40 am - 9:55 am

MDW

CLE

1h 15mnonstop

$167Southwest

Wed, Aug 12 - Sat, Aug 15

12:25 pm - 4:00 pm

CLE

MDW

4h 35m

1 stop

3:50 pm - 9:00 pm

MDW

CLE

4h 10m

1 stop

$172Southwest

Sat, Oct 3 - Tue, Oct 6

5:30 am - 6:07 am

CLE

ORD

1h 37mnonstop

8:45 am - 11:27 am

ORD

CLE

1h 42mnonstop

$174United Airlines

Wed, Sep 23 - Wed, Sep 23

7:00 am - 7:36 am

CLE

ORD

1h 36mnonstop

2:20 pm - 4:54 pm

ORD

CLE

1h 34mnonstop

$177United Airlines

Tue, Aug 4 - Tue, Aug 4

1:15 pm - 9:50 pm

CLE

MDW

9h 35m

2 stops

6:35 am - 1:15 pm

MDW

CLE

5h 40m

1 stop

$177Southwest

Wed, Aug 12 - Sat, Aug 15

8:47 pm - 9:30 pm

CLE

ORD

1h 43mnonstop

11:30 am - 2:02 pm

ORD

CLE

1h 32mnonstop

$182American Airlines

Tue, Jun 30 - Tue, Jul 7

6:43 am - 9:17 am

CLE

MDW

3h 34m

1 stop

9:24 am - 1:40 pm

MDW

CLE

3h 16m

1 stop

$186Delta

Wed, Aug 26 - Sat, Aug 29

3:49 pm - 8:30 pm

CLE

ORD

5h 41m

1 stop

7:00 am - 1:40 pm

ORD

CLE

5h 40m

1 stop

$186Delta

Wed, Aug 26 - Sat, Aug 29

2:59 pm - 12:25 pm

CLE

ORD

22h 26m

1 stop

7:55 am - 9:57 pm

ORD

CLE

13h 02m

1 stop

$191Frontier

Wed, Aug 26 - Wed, Sep 2

5:15 am - 5:46 am

CLE

ORD

1h 31mnonstop

11:45 am - 2:20 pm

ORD

CLE

1h 35mnonstop

$193American Airlines

Wed, Aug 12 - Fri, Aug 14

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United Airlines flights from Cleveland to Chicago

Our best United Airlines deals on Cleveland to Chicago flight tickets

United Airlines

Sep 23

CLE5:30 amCleveland Hopkins Intl

1h 37m

ORD6:07 amChicago O'Hare Intl

Sep 23

ORD8:45 amChicago O'Hare Intl

1h 42m

CLE11:27 amCleveland Hopkins Intl

$174

United Airlines

Aug 4

CLE7:00 amCleveland Hopkins Intl

1h 36m

ORD7:36 amChicago O'Hare Intl

Aug 4

ORD2:20 pmChicago O'Hare Intl

1h 34m

CLE4:54 pmCleveland Hopkins Intl

$177

United Airlines

Jul 15

CLE6:00 amCleveland Hopkins Intl

1h 40m

ORD6:40 amChicago O'Hare Intl

Jul 29

ORD2:20 pmChicago O'Hare Intl

1h 34m

CLE4:54 pmCleveland Hopkins Intl

$179

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets

Frontier

Aug 26

CLE2:59 pmCleveland Hopkins Intl

22h 26m

1 stop

ORD12:25 pmChicago O'Hare Intl

Sep 2

ORD7:55 amChicago O'Hare Intl

13h 02m

1 stop

CLE9:57 pmCleveland Hopkins Intl

$191

Frontier

Aug 24

CLE3:46 pmCleveland Hopkins Intl

17h 17m

1 stop

ORD8:03 amChicago O'Hare Intl

Aug 26

ORD7:55 amChicago O'Hare Intl

13h 02m

1 stop

CLE9:57 pmCleveland Hopkins Intl

$206

Frontier

Aug 4

CLE8:22 pmCleveland Hopkins Intl

10h 15m

1 stop

ORD5:37 amChicago O'Hare Intl

Aug 5

ORD9:57 pmChicago O'Hare Intl

12h 01m

1 stop

CLE10:58 amCleveland Hopkins Intl

$210

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 8/12

1:15 pm-9:50 pm

2 stops9h 35m

Chicago Midway

Sat 8/15

7:40 am-9:55 am

Nonstop1h 15m

$167

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 10/3

12:25 pm-4:00 pm

1 stop4h 35m

Chicago Midway

Tue 10/6

3:50 pm-9:00 pm

1 stop4h 10m

$172

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 9/23

5:30 am-6:07 am

Nonstop1h 37m

Chicago O'Hare Intl

Wed 9/23

8:45 am-11:27 am

Nonstop1h 42m

$174

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 8/4

7:00 am-7:36 am

Nonstop1h 36m

Chicago O'Hare Intl

Tue 8/4

2:20 pm-4:54 pm

Nonstop1h 34m

$177

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 8/12

1:15 pm-9:50 pm

2 stops9h 35m

Chicago Midway

Sat 8/15

6:35 am-1:15 pm

1 stop5h 40m

$177

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 6/30

8:47 pm-9:30 pm

Nonstop1h 43m

Chicago O'Hare Intl

Tue 7/7

11:30 am-2:02 pm

Nonstop1h 32m

$182

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 8/26

6:43 am-9:17 am

1 stop3h 34m

Chicago Midway

Sat 8/29

9:24 am-1:40 pm

1 stop3h 16m

$186

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 8/26

3:49 pm-8:30 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 8/29

7:00 am-1:40 pm

1 stop5h 40m

$186

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 8/26

2:59 pm-12:25 pm

1 stop22h 26m

Chicago O'Hare Intl

Wed 9/2

7:55 am-9:57 pm

1 stop13h 02m

$191

Quickest round-trip

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 8/12

5:15 am-5:46 am

Nonstop1h 31m

Chicago O'Hare Intl

Fri 8/14

11:45 am-2:20 pm

Nonstop1h 35m

$193

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 May is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $83. If you’re not able to fly to Chicago in May, then August is your next best option. Flight prices from Cleveland to Chicago during August average around $85.

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 $452. 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 $637.

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 $463. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $766.

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 from Cleveland 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 $309 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 $164 on momondo.

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

There are 4 cabin classes available to choose from on Cleveland 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 June 2026, prices for Cleveland to Chicago flights are approximately 77% 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	$215
Fastest flight time	1h 10m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Cleveland in the past 72 hours is $215. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $252.

The fastest flight from Cleveland to Chicago takes 1h 10m

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

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 10m.
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 June 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 13.52% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 13.35%, Airbus A319 at 11.60%, and Airbus A320-100/200 at 9.96%.
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 47% of all bookings. The subsequent popular airlines are Southwest at 28%, American Airlines at 21%, 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
Frontier	PriceFrom $107	Free Cancellation	Rating 5.6 2,888 reviews	Search Frontier flights
American Airlines	PriceFrom $127	Free Cancellation	Rating 7.1 11,661 reviews	Search American Airlines flights
Southwest	PriceFrom $139	Free Cancellation	Rating 7.9 4,235 reviews	Search Southwest flights
United Airlines	PriceFrom $146	Free Cancellation	Rating 7.4 9,828 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 18 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 9,828 reviews) operates around 47 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $315, with deals from around $146 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

Portage

Saint Joseph

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 $98

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 8/6. 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

Our best United Airlines deals on Cleveland to Chicago flight tickets

Frontier flights from Cleveland to Chicago

Our best Frontier 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 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 from Cleveland to Chicago?

What cabin class options are available on Cleveland 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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