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$59+ 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 9/19. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Aug 30 — Sep 61
Sun 8/30
Sun 9/6
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in May or March, booked 60 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap 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 31, 2026.

This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
CLE
-
MDW
2 stops6h 35m
Southwest
Mon 8/244:25 pm
MDW
-
CLE
Nonstop1h 15m
Southwest
Deal found 7/30$132
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:59 pm
CLE
-
ORD
1 stop13h 21m
Frontier
Mon 9/287:11 am
ORD
-
CLE
1 stop11h 51m
Frontier
Deal found 7/30$135
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:05 pm
CLE
-
MDW
1 stop5h 15m
Southwest
Mon 8/247:30 am
MDW
-
CLE
1 stop3h 45m
Southwest
Deal found 7/27$137
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:40 am
CLE
-
MDW
2 stops6h 35m
Southwest
Wed 8/2612:45 pm
MDW
-
CLE
2 stops7h 15m
Southwest
Deal found 7/29$147
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:38 pm
CLE
-
ORD
1 stop21h 12m
Frontier
Wed 9/28:05 am
ORD
-
CLE
1 stop14h 24m
Frontier
Deal found 7/29$151
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:49 pm
CLE
-
MDW
1 stop8h 04m
Frontier
Sat 11/147:25 am
MDW
-
CLE
1 stop5h 04m
Frontier
Deal found 7/30$152
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:37 pm
CLE
-
ORD
1 stop10h 31m
Frontier
Tue 9/88:05 am
ORD
-
CLE
1 stop14h 24m
Frontier
Deal found 7/30$153
This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:43 am
CLE
-
MDW
1 stop3h 34m
Delta
Sat 8/299:24 am
MDW
-
CLE
1 stop3h 16m
Delta
Deal found 7/29$157
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/263:49 pm
CLE
-
ORD
1 stop5h 41m
Delta
Sat 8/295:18 pm
ORD
-
CLE
1 stop3h 04m
Delta
Deal found 7/30$157
This Expedia deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:00 am
CLE
-
MDW
1 stop12h 31m
Frontier
Fri 8/2111:50 am
MDW
-
CLE
1 stop9h 41m
Frontier
Deal found 7/30$159
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/287:00 am
CLE
-
ORD
1 stop13h 02m
Frontier
Sat 8/291:59 pm
ORD
-
CLE
1 stop7h 32m
Frontier
Deal found 7/29$159
This Priceline deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:40 pm
CLE
-
MDW
1 stop7h 18m
Frontier
Sun 10/1112:03 pm
MDW
-
CLE
1 stop7h 34m
Frontier
Deal found 7/30$163

Find flight deals from Cleveland to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(Southwest)

One-way from

$59
(Southwest)

Popular in

January

Cheapest in

May

Average price

$277

Good round-trip deal

$237 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Cleveland Hopkins Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-Chicago (CHI) flights.
Search Deals
From Cleveland Hopkins Intl to Chicago (CHI)
Search Deals
One-way flight from Cleveland Hopkins Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Cleveland Hopkins Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Cleveland Hopkins Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2026.
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

Cheapest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 10/7

6:15 am-12:05 pm

2 stops6h 50m

Chicago Midway

Thu 10/8

5:00 am-12:00 pm

1 stop6h 00m

$142

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 9/29

8:28 am-10:37 am

1 stop3h 09m

Chicago O'Hare Intl

Tue 10/6

8:29 am-1:39 pm

1 stop4h 10m

$157

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 8/25

3:49 pm-8:30 pm

1 stop5h 41m

Chicago O'Hare Intl

Sat 8/29

5:18 pm-9:22 pm

1 stop3h 04m

$157

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

5:18 pm-9:22 pm

1 stop3h 04m

$157

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 8/22

6:10 am-1:20 pm

2 stops8h 10m

Chicago Midway

Sat 8/29

5:55 am-12:15 pm

1 stop5h 20m

$159

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 10/12

8:10 am-10:30 am

1 stop3h 20m

Chicago O'Hare Intl

Mon 10/12

7:30 pm-11:46 pm

1 stop3h 16m

$164

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 10/9

6:10 pm-6:50 pm

Nonstop1h 40m

Chicago O'Hare Intl

Wed 10/14

10:40 am-1:11 pm

Nonstop1h 31m

$168

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 9/18

2:14 pm-2:52 pm

Nonstop1h 38m

Chicago O'Hare Intl

Mon 9/21

9:30 pm-11:59 pm

Nonstop1h 29m

$168
Quickest round-trip

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 10/8

8:20 pm-8:35 pm

Nonstop1h 15m

Chicago Midway

Fri 10/9

6:45 pm-8:55 pm

Nonstop1h 10m

$168

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 8/21

5:30 am-6:07 am

Nonstop1h 37m

Chicago O'Hare Intl

Wed 9/9

8:45 am-11:27 am

Nonstop1h 42m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 57 resultsSorted by cheapest first
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Compare providers for flights from Cleveland to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Cleveland to Chicago in July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
JustAirTicketPrice Accuracy-Trust Score*1 star
Trip.comPrice Accuracy1 starTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Cleveland-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cleveland-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Cleveland-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

Currently, May is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $251). Flying from Cleveland to Chicago in January is currently the most expensive (average of $365). 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?

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 31, 2026.

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 28% on your trip compared to booking a flight at noon.

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 31, 2026.

The most flights from CLE to CHI are scheduled on a Thursday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (36 on average).

How much does it cost to fly round-trip from Cleveland to Chicago?

Airfare is below average for this route at the moment.
Cleveland to Chicago flights typically cost between $166 and $294 in August.
The cheapest round-trip price found within the last 5 days was $132 on Southwest (Aug 24-Aug 24).

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

Booking 53 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 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 July 25, 2026.

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

The best insider tips for Cleveland to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Cleveland to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and CLE

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 31, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican 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
4,226 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,226 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,051 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,842 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Frontier
5.6
Fair
2,747 reviews
Southwest
8.0
Very good
4,226 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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?

    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 49 outbound flights to Chicago per day.

  • How long is the flight from Cleveland to Chicago?

    Airlines like Southwest, Delta, and United Airlines fly from Cleveland to Chicago in about 1h 40m. The time it takes to get you to your destination can typically vary by up to 5h 10m. There are 315 mi between Cleveland and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $128 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $137 and $142 round-trip. American Airlines is currently priced 52% 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 $68 on American Airlines. Other airlines that offer cheap prices include United Airlines from $86 and Frontier from $87 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 Envoy Air (89%), Japan Airlines (80%) or ANA (80%) 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 $1,731, our data indicates the cheapest price to be $141. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $117.

  • 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, May is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $251). Flying from Cleveland to Chicago in January is currently the most expensive (average of $365). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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Top 4 airlines flying from Cleveland to Chicago

Discover the top 4 airlines that operate flights from Cleveland to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$128Average$266FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$137Average$263FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$142Average$321FlexibilityNo cancel feeOn-time69%
FrontierCheapest$143Average$201FlexibilityNo cancel feeOn-time62%

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