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$64+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in August or April, booked 88 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 December 23, 2025.

This Delta deal was found by Cheapflights users on 12/22. 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 12/315:58 pmCLE - ORD
1 stop7h 04mDelta
Thu 1/11:35 pmORD - CLE
2 stops6h 55mDelta
Deal found 12/22$202
This Frontier deal was found by Cheapflights users on 12/21. 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.
Wed 12/316:20 amCLE - MDW
1 stop8h 01mFrontier
Sun 1/410:50 pmMDW - CLE
1 stop11h 17mFrontier
Deal found 12/21$214
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amCLE - ORD
1 stop7h 40mAmerican Airlines
Thu 1/14:56 pmORD - CLE
Nonstop1h 24mAmerican Airlines
Deal found 12/21$217
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:43 amCLE - ORD
Nonstop1h 42mUnited Airlines
Wed 12/317:35 pmORD - CLE
Nonstop1h 29mUnited Airlines
Deal found 12/20$237
This Expedia deal was found by Cheapflights users on 12/21. 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 12/258:20 pmCLE - ORD
1 stop28h 52mFrontier
Thu 1/112:39 pmORD - CLE
1 stop9h 34mFrontier
Deal found 12/21$238
This American Airlines deal was found by Cheapflights users on 12/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:33 amCLE - ORD
Nonstop1h 47mAmerican Airlines
Wed 12/249:45 amORD - CLE
1 stop22h 45mAmerican Airlines
Deal found 12/21$255
This Southwest deal was found by Cheapflights users on 12/20. 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.
Wed 12/316:45 amCLE - MDW
Nonstop1h 35mSouthwest
Sat 1/312:45 pmMDW - CLE
Nonstop1h 10mSouthwest
Deal found 12/20$260
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/316:20 amCLE - ORD
1 stop13h 13mFrontier
Fri 1/25:45 amORD - CLE
1 stop6h 38mFrontier
Deal found 12/20$277
This Frontier deal was found by Cheapflights users on 12/20. 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 12/265:13 pmCLE - ORD
1 stop7h 59mFrontier
Wed 12/3112:39 pmORD - CLE
1 stop9h 34mFrontier
Deal found 12/20$282
This Kiwi.com deal was found by Cheapflights users on 12/20. 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 12/316:20 amCLE - ORD
1 stop13h 13mMultiple Airlines
Thu 1/17:20 amORD - CLE
2 stops16h 23mMultiple Airlines
Deal found 12/20$283
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/316:20 amCLE - MDW
1 stop8h 01mFrontier
Thu 1/16:12 amMDW - CLE
1 stop16h 01mFrontier
Deal found 12/21$289
This Frontier deal was found by Cheapflights users on 12/20. 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 12/2511:26 amCLE - ORD
1 stop8h 07mFrontier
Wed 12/3112:39 pmORD - CLE
1 stop9h 34mFrontier
Deal found 12/20$292

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 December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$201
(Kiwi.com)

One-way from

$64
(Frontier)

Popular in

January

Cheapest in

August

Average price

$297

Good round-trip deal

$339 or less

Good one-way deal

$170 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. 9% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 2025.
Use the filters below to find and compare flights from Cleveland to Chicago that are best for you.

Fly from

Cleveland

Fly to

Chicago

Route

Depart

Return

Price

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 1/17

6:00 am-12:48 pm

2 stops7h 48m

Chicago Midway

Sun 1/18

11:21 am-5:51 pm

1 stop5h 30m

$202

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sat 1/17

12:29 pm-9:05 pm

2 stops9h 36m

Chicago O'Hare Intl

Tue 1/20

5:30 am-1:22 pm

1 stop6h 52m

$202

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 4/9

7:10 am-11:33 am

1 stop5h 23m

Chicago Midway

Sat 4/11

12:33 pm-12:21 am

1 stop10h 48m

$204

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Fri 1/23

11:53 am-7:52 pm

1 stop8h 59m

Chicago Midway

Mon 1/26

5:01 pm-1:44 pm

2 stops19h 43m

$205

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 12/31

12:28 pm-8:36 pm

2 stops9h 08m

Chicago O'Hare Intl

Thu 1/1

1:35 pm-11:32 pm

2 stops8h 57m

$207

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/6

8:25 pm-10:17 pm

2 stops26h 52m

Chicago Midway

Sat 1/10

6:10 am-11:13 pm

1 stop16h 03m

$218

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Mon 1/26

6:15 am-6:55 am

Nonstop1h 40m

Chicago Midway

Wed 1/28

7:55 pm-10:10 pm

Nonstop1h 15m

$224

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 1/5

12:17 pm-11:54 pm

2 stops12h 37m

Chicago O'Hare Intl

Wed 1/7

5:50 am-11:13 pm

1 stop16h 23m

$227

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Wed 1/14

6:30 am-8:52 am

1 stop3h 22m

Chicago Midway

Wed 1/14

1:28 pm-6:55 pm

1 stop4h 27m

$231

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Tue 1/13

12:55 pm-4:29 pm

1 stop4h 34m

Chicago Midway

Wed 1/14

9:32 am-3:10 pm

1 stop4h 38m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 49 results
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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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Trip.comPrice Accuracy2 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Cleveland-Chicago flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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 December 19, 2025.

Booking 76 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, November is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $53). Flying from Cleveland to Chicago in July is currently the most expensive (average of $121). 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 December 23, 2025.

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.

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 December 20, 2025.

Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Tuesday at noon when fares are most often at their lowest. Sunday 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

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 December 23, 2025.

The most flights from CLE to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).

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
Airports
CLE

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

Read more about CLEBy Ramsey Qubein
ORD

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

Read more about ORDBy Ramsey Qubein
MDW

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

Read more about MDWBy Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD, MDW and CLE

Ramsey Qubein

Ramsey Qubein

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 December 23, 2025.
Get a feel of what it's like to fly with Southwest, United Airlines, and American 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
4,253 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,106 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,074 reviews
Southwest
8.0
Very good
4,253 reviews

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 31 outbound flights to Chicago per day.

  • How long is the flight from Cleveland to Chicago?

    Airlines like Delta, Frontier, and Southwest 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 6h 08m. There are 305 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 $133 on this airline. Additional options worth looking into are Southwest and Frontier, starting at $140 and $143 round-trip. American Airlines is currently priced 51% 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 $65 on Frontier. Other airlines that offer cheap prices include American Airlines from $77 and Southwest from $88 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 (83%), Lufthansa (80%) or Austrian Airlines (78%) 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 $948, our data indicates the cheapest price to be $114. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $137.

  • 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, November is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $53). Flying from Cleveland to Chicago in July is currently the most expensive (average of $121). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
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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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$133Average$294FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$140Average$271FlexibilityNo cancel feeOn-time63%
FrontierCheapest$143Average$166FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$157Average$296FlexibilityNo cancel feeOn-time69%

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