What are the cheapest airlines flying from Cleveland to Chicago round-trip?

Our cheapest airline available from Cleveland to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $151 on this airline. Additional options worth looking into are Southwest and Frontier, starting at $152 and $156 round-trip. American Airlines is currently priced 44% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Cleveland to Chicago one-way?

One-way options have recently been found by users for as low as $71 on Frontier. Other airlines that offer cheap prices include Southwest from $74 and Delta from $89 one-way.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Cleveland to Chicago?

When deciding which route to take from Cleveland to Chicago consider Cleveland Hopkins Intl - Chicago O'Hare Intl, Cleveland Hopkins Intl - Chicago Midway or Cleveland Hopkins Intl - Chicago Greater Rockford as they are the most popular.

What are the cheapest flights from Cleveland to Chicago?

Looking for the cheapest flight from Cleveland to Chicago? While on average our users pay $1,552, our data indicates the cheapest price to be $124. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $127.

What are the most reliable airlines from Cleveland to Chicago?

Consider SWISS (94%), Copa Airlines (93%) or Austrian Airlines (92%) when booking your flight. These represent the most reliable airlines when flying from Cleveland to Chicago.

What are the most popular airlines that fly from Cleveland to Chicago?

Consider American Airlines, Frontier or United Airlines when booking your flight. These represent the most popular airlines when flying from Cleveland to Chicago.

What is the cheapest day to fly round-trip from Cleveland to Chicago?

Travelers have found that booking a Thursday departure is the best way to save up to 38% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

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

To save up to 275% on this flight, we recommend booking at least 58 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Cleveland to Chicago from $360 1-2 weeks out and tickets from $640 for flights departing within the next 72 hours.

What is the cheapest month to fly from Cleveland to Chicago?

September can be a great time to fly to Chicago from Cleveland with a flight ticket averaging about $274. Cheapflights users have found deals in the month of September for as cheap as $129. The most expensive prices can be found in the month of February.

What airport do you fly from for flights from Cleveland to Chicago?

Cleveland Hopkins Intl (CLE), located 10.1 mi from the city center, is the airport you fly out of when you book flights from Cleveland to Chicago. 4 airlines have flights from Hopkins Intl to Chicago on a regular basis. Booking flights from Cleveland Hopkins Intl to Chicago should not be difficult; the airport handles an average of 36 outbound flights to Chicago per day.

Can I find deals for flights from Cleveland to Chicago that include hotel bookings?

Yes. In addition to deals on Cleveland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Cleveland to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Chicago.

Can I find deals for business class flights from Cleveland to Chicago?

Yes. Cheapflights offers flight deals from Cleveland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$71+ Flights from Cleveland to Chicago

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in September or April, booked 77 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap flight deals from Cleveland to Chicago

Round-trip from	$151 (American Airlines)
One-way from	$71 (Priceline)
Popular in	February
Cheapest in	September
Average price	$277
Good round-trip deal	$289 or less
Good one-way deal	$184 or less

From Cleveland Hopkins Intl to Chicago (CHI)

Search Deals

One-way flight from Cleveland Hopkins Intl to Chicago (CHI)

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Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Price to beat on a round-trip flight from Cleveland Hopkins Intl to Chicago (CHI).

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Price to beat on a one-way flight from Cleveland Hopkins Intl to Chicago (CHI).

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Find flight deals from Cleveland to Chicago

Cheapest flights from Cleveland to Chicago
Explore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.

Fri 8/226:45 amCLE - MDW

Nonstop1h 15mSouthwest

Sun 8/241:45 pmMDW - CLE

Nonstop1h 15mSouthwest

Deal found 7/1

$151

Fri 8/156:45 amCLE - ORD

Nonstop1h 31mAmerican Airlines

Sun 8/1710:11 pmORD - CLE

Nonstop1h 18mAmerican Airlines

Deal found 7/1

$151

Mon 9/86:15 amCLE - ORD

1 stop11h 10mSouthwest

Wed 9/103:10 pmORD - CLE

1 stop5h 10mSouthwest

Deal found 7/1

$152

Fri 8/2912:20 pmCLE - MDW

1 stop6h 45mFrontier

Sun 8/319:17 amMDW - CLE

1 stop6h 19mFrontier

Deal found 6/30

$156

Thu 7/37:26 pmCLE - ORD

1 stop5h 48mFrontier

Sat 7/57:00 amORD - CLE

1 stop9h 52mFrontier

Deal found 6/29

$156

Sun 8/105:30 amCLE - MDW

1 stop4h 14mDelta

Thu 8/219:31 amMDW - CLE

1 stop3h 01mDelta

Deal found 6/30

$177

Sun 8/105:30 amCLE - ORD

1 stop5h 46mDelta

Wed 8/135:45 amORD - CLE

1 stop4h 38mDelta

Deal found 6/30

$177

Sat 8/96:00 amCLE - ORD

Nonstop1h 28mUnited Airlines

Tue 8/192:27 pmORD - CLE

Nonstop1h 24mUnited Airlines

Deal found 6/30

$187

Sat 7/1912:37 pmCLE - ORD

2 stops19h 27mSpirit Airlines

Wed 7/236:02 pmORD - CLE

2 stops16h 30mSpirit Airlines

Deal found 6/30

$220

Thu 7/107:47 pmCLE - RFD

2 stops24h 32mMultiple Airlines

Sun 7/139:21 amRFD - CLE

1 stop8h 31mMultiple Airlines

Deal found 6/28

$321

Best flights from Cleveland to Chicago
Discover carefully curated flight deals from Cleveland to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 1, 2025.

Fri 8/156:45 amCLE - ORD

Nonstop1h 31mAmerican Airlines

Sun 8/1710:11 pmORD - CLE

Nonstop1h 18mAmerican Airlines

Deal found 7/1

$151

Mon 9/86:15 amCLE - ORD

1 stop11h 10mSouthwest

Wed 9/103:10 pmORD - CLE

1 stop5h 10mSouthwest

Deal found 7/1

$152

Fri 8/2912:20 pmCLE - MDW

1 stop6h 45mFrontier

Sun 8/319:17 amMDW - CLE

1 stop6h 19mFrontier

Deal found 6/30

$156

Sun 8/105:30 amCLE - MDW

1 stop4h 14mDelta

Thu 8/219:31 amMDW - CLE

1 stop3h 01mDelta

Deal found 6/30

$177

Sat 8/96:00 amCLE - ORD

Nonstop1h 28mUnited Airlines

Thu 8/219:31 pmORD - CLE

Nonstop1h 28mUnited Airlines

Deal found 6/30

$187

Sat 7/1912:37 pmCLE - ORD

2 stops19h 27mSpirit Airlines

Wed 7/236:02 pmORD - CLE

2 stops16h 30mSpirit Airlines

Deal found 6/30

$220

Fri 8/223:30 pmCLE - MDW

Nonstop1h 20mSouthwest

Mon 8/253:25 pmMDW - CLE

2 stops6h 45mSouthwest

Deal found 6/30

$154

Thu 7/177:26 pmCLE - ORD

1 stop5h 56mFrontier

Sat 7/195:07 pmORD - CLE

1 stop5h 57mFrontier

Deal found 6/29

$156

Thu 7/107:47 pmCLE - RFD

2 stops24h 32mMultiple Airlines

Sun 7/139:21 amRFD - CLE

1 stop8h 31mMultiple Airlines

Deal found 6/28

$321

Sun 8/105:30 amCLE - ORD

1 stop3h 19mDelta

Wed 8/209:10 amORD - CLE

1 stop3h 22mDelta

Deal found 6/30

$177

Last-minute flights from Cleveland to Chicago
Discover last-minute flight deals from Cleveland to Chicago. Data last updated July 1, 2025 and is based on user searches.

Thu 7/37:26 pmCLE - ORD

1 stop5h 48mFrontier

Sat 7/57:00 amORD - CLE

1 stop9h 52mFrontier

Deal found 6/29

$156

Thu 7/107:26 pmCLE - ORD

1 stop5h 56mFrontier

Sat 7/127:00 amORD - CLE

1 stop9h 52mFrontier

Deal found 6/29

$186

Thu 7/105:30 amCLE - MDW

1 stop9h 17mFrontier

Thu 7/102:55 pmMDW - CLE

1 stop8h 44mFrontier

Deal found 6/29

$209

Thu 7/1012:37 pmCLE - ORD

2 stops19h 27mSpirit Airlines

Fri 7/186:02 pmORD - CLE

2 stops16h 30mSpirit Airlines

Deal found 6/29

$255

Thu 7/107:47 pmCLE - RFD

2 stops24h 32mMultiple Airlines

Sun 7/139:21 amRFD - CLE

1 stop8h 31mMultiple Airlines

Deal found 6/28

$321

Fri 7/1111:00 amCLE - MDW

Nonstop1h 15mSouthwest

Mon 7/1410:55 pmMDW - CLE

Nonstop1h 15mSouthwest

Deal found 6/30

$472

Fri 7/115:30 amCLE - MDW

1 stop4h 14mDelta

Sun 7/139:25 amMDW - CLE

1 stop3h 04mDelta

Deal found 6/28

$511

Sat 7/1912:37 pmCLE - ORD

2 stops19h 27mSpirit Airlines

Wed 7/236:02 pmORD - CLE

2 stops16h 30mSpirit Airlines

Deal found 6/30

$220

Tue 7/298:50 amCLE - ORD

Nonstop1h 33mUnited Airlines

Mon 8/47:35 pmORD - CLE

Nonstop1h 25mUnited Airlines

Deal found 6/29

$187

Sun 8/105:30 amCLE - MDW

1 stop4h 14mDelta

Thu 8/219:31 amMDW - CLE

1 stop3h 01mDelta

Deal found 6/30

$177

Sun 8/105:30 amCLE - ORD

1 stop5h 46mDelta

Wed 8/135:45 amORD - CLE

1 stop4h 38mDelta

Deal found 6/30

$177

Tue 8/125:35 amCLE - ORD

1 stop7h 15mSouthwest

Thu 8/141:50 pmORD - CLE

1 stop8h 20mSouthwest

Deal found 7/1

$152

One-way flights from Cleveland to Chicago
Search for one-way flight options from Cleveland to Chicago. Find affordable one-way fares based on user searches. Data last updated July 1, 2025.

Mon 8/186:01 pmCLE - ORD

1 stop7h 04mFrontier

Deal found 6/30

$71

Wed 9/34:00 pmCLE - MDW

1 stop4h 45mSouthwest

Deal found 6/30

$74

Sat 9/136:15 amCLE - ORD

1 stop11h 10mSouthwest

Deal found 6/30

$79

Sun 8/316:00 amCLE - MDW

1 stop5h 08mFrontier

Deal found 6/30

$81

Wed 7/305:30 amCLE - MDW

1 stop4h 14mDelta

Deal found 6/30

$89

Wed 7/305:30 amCLE - ORD

1 stop3h 19mDelta

Deal found 6/30

$89

Thu 9/113:02 pmCLE - ORD

2 stops20h 38mSpirit Airlines

Deal found 6/30

$102

Sat 8/212:37 pmCLE - RFD

2 stops20h 54mMultiple Airlines

Deal found 6/30

$132

Sun 7/1312:37 pmCLE - MDW

2 stops22h 04mMultiple Airlines

Deal found 6/29

$179

Cheapflights Fare Finder

Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 8/22

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Sun 8/24

1:45 pm-4:00 pm

Nonstop1h 15m

$151

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 8/15

6:45 am-7:16 am

Nonstop1h 31m

Chicago O'Hare Intl

Sun 8/17

10:11 pm-12:29 am

Nonstop1h 18m

$151

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 8/12

5:35 am-11:50 am

1 stop7h 15m

Chicago O'Hare Intl

Thu 8/14

1:50 pm-11:10 pm

1 stop8h 20m

$152

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 8/29

12:20 pm-6:05 pm

1 stop6h 45m

Chicago Midway

Sun 8/31

9:17 am-4:36 pm

1 stop6h 19m

$156

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 7/17

7:26 pm-12:22 am

1 stop5h 56m

Chicago O'Hare Intl

Sat 7/19

5:07 pm-12:04 am

1 stop5h 57m

$156

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sun 8/10

5:30 am-8:44 am

1 stop4h 14m

Chicago Midway

Thu 8/21

9:31 am-1:32 pm

1 stop3h 01m

$177

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sun 8/10

5:30 am-7:49 am

1 stop3h 19m

Chicago O'Hare Intl

Wed 8/20

9:10 am-1:32 pm

1 stop3h 22m

$177

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 7/29

7:00 am-7:33 am

Nonstop1h 33m

Chicago O'Hare Intl

Tue 8/5

7:33 am-9:59 am

Nonstop1h 26m

$187

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 7/19

12:37 pm-7:04 am

2 stops19h 27m

Chicago O'Hare Intl

Wed 7/23

6:02 pm-11:32 am

2 stops16h 30m

$220

ClevelandChicago

CLE - RFD

CLERFD

Cleveland Hopkins Intl

Thu 7/10

7:47 pm-7:19 pm

2 stops24h 32m

Chicago Greater Rockford

Sun 7/13

9:21 am-6:52 pm

1 stop8h 31m

$321

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 19 results

1

2

The best insider tips for Cleveland to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago trip

Airlines

Qatar Airways

Qatar Airways' carry-on policy allows only one item in economy class.

Qatar's business class offers luxury with lie-flat seats and gourmet dining.

Read more about Qatar Airwaysby Brandon Schultz

United Airlines

United's Economy Plus offers extra legroom, ideal for a comfortable short-haul experience.

Prepay for checked bags on United to save fees on domestic flights.

Read more about United Airlinesby Harriet Baskas

Southwest

Southwest offers two free checked bags, a standout feature among low-cost carriers.

Enjoy free in-flight entertainment on Southwest, streamed directly to your device.

Read more about Southwestby Marisa Garcia

Airports

CLE

CLE offers complimentary Wi-Fi throughout the terminal, with charging stations and work stations available in each concourse.

ORD

ORD's free shuttle train connects terminals, making it easier to navigate the airport's sprawling layout.

MDW

The Orange Line train connects MDW to downtown Chicago in under 30 minutes, offering a convenient and affordable transit option.

Our travel experts

Brandon Schultz

Expert on Qatar Airways

Harriet Baskas

Expert on United Airlines

Marisa Garcia

Expert on Southwest

Ramsey Qubein

Expert on ORD, MDW and CLE

Best time to book a flight from Cleveland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cleveland with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Cleveland to Chicago

How far ahead should I book a flight from Cleveland to Chicago?

Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Cleveland to Chicago?

Currently, August is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $245). Flying from Cleveland to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CLE to CHI?

A simple way to save on the total cost of your ticket is to fly from Cleveland to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 47% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Cleveland to Chicago?

Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Wednesday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Cleveland to Chicago

The most flights from CLE to CHI are scheduled on a Monday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Cleveland to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,273 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,973 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

United Airlines

7.4

Good

8,858 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Spirit Airlines

6.3

Okay

8,101 reviews

Southwest

8.0

Very good

4,273 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly from for flights from Cleveland to Chicago?
Cleveland Hopkins Intl (CLE), located 10.1 mi from the city center, is the airport you fly out of when you book flights from Cleveland to Chicago. 4 airlines have flights from Hopkins Intl to Chicago on a regular basis. Booking flights from Cleveland Hopkins Intl to Chicago should not be difficult; the airport handles an average of 36 outbound flights to Chicago per day.
What are the cheapest airlines flying from Cleveland to Chicago round-trip?
Our cheapest airline available from Cleveland to Chicago is American Airlines. Our recent data shows that you can find tickets from as low as $151 on this airline. Additional options worth looking into are Southwest and Frontier, starting at $152 and $156 round-trip. American Airlines is currently priced 44% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Cleveland to Chicago one-way?
One-way options have recently been found by users for as low as $71 on Frontier. Other airlines that offer cheap prices include Southwest from $74 and Delta from $89 one-way.
What are the most popular routes from Cleveland to Chicago?
When deciding which route to take from Cleveland to Chicago consider Cleveland Hopkins Intl - Chicago O'Hare Intl, Cleveland Hopkins Intl - Chicago Midway or Cleveland Hopkins Intl - Chicago Greater Rockford as they are the most popular.
What are the most reliable airlines from Cleveland to Chicago?
Consider SWISS (94%), Copa Airlines (93%) or Austrian Airlines (92%) when booking your flight. These represent the most reliable airlines when flying from Cleveland to Chicago.
What are the cheapest flights from Cleveland to Chicago?
Looking for the cheapest flight from Cleveland to Chicago? While on average our users pay $1,552, our data indicates the cheapest price to be $124. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $127.
Can I find deals for flights from Cleveland to Chicago that include hotel bookings?
Yes. In addition to deals on Cleveland to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Cleveland to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Chicago.
Can I find deals for business class flights from Cleveland to Chicago?
Yes. Cheapflights offers flight deals from Cleveland to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Cleveland to Chicago?
Currently, August is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $245). Flying from Cleveland to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Merrillville

Lansing

Benton Harbor

Porter

Hammond

Valparaiso

Chesterton

Browse thousands of different options on Cheapflights for your next trip

Top 4 airlines flying from Cleveland to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$100	Average$153	FlexibilityNo cancel fee	On-time62%
Southwest	Cheapest$151	Average$273	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$157	Average$312	FlexibilityNo cancel fee	On-time69%
American Airlines	Cheapest$157	Average$293	FlexibilityNo cancel fee	On-time71%

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$71+ Cheap flights from Cleveland (CLE) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Cleveland to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in September or April, booked 77 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap flight deals from Cleveland to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals from Cleveland to Chicago

Cheapest flights from Cleveland to ChicagoExplore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.

Explore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.

The best insider tips for Cleveland to Chicago flights

Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago trip

Airlines

Qatar Airways

United Airlines

Southwest

Airports

CLE

ORD

MDW

Our travel experts

Best time to book a flight from Cleveland to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cleveland with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Cleveland to Chicago

How far ahead should I book a flight from Cleveland to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Cleveland to Chicago. Price data was last updated on June 27, 2025.

What is the cheapest month to book a flight from Cleveland to Chicago?

What is the cheapest time of day to fly from CLE to CHI?

Find hourly flight availability from Cleveland to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 1, 2025.

What is the cheapest day to fly from Cleveland to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Chicago. Price data was last updated on June 29, 2025.

Weekly flight availability from Cleveland to Chicago

Explore weekly flight availability from Cleveland to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 1, 2025.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Cleveland to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Cleveland to Chicago?

What are the cheapest airlines flying from Cleveland to Chicago round-trip?

What are the cheapest airlines to fly from Cleveland to Chicago one-way?

What are the most popular routes from Cleveland to Chicago?

What are the most reliable airlines from Cleveland to Chicago?

What are the cheapest flights from Cleveland to Chicago?

Can I find deals for flights from Cleveland to Chicago that include hotel bookings?

How can I find direct flights from Cleveland to Chicago?

Can I find deals for business class flights from Cleveland to Chicago?

What is the cheapest month to book a flight from Cleveland to Chicago?

Traveling to a place near Cleveland?

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Alternative routes for Cleveland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 4 airlines flying from Cleveland to Chicago

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Cheapest flights from Cleveland to Chicago
Explore the most affordable flight options available from Cleveland to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.