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$70+ 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in April or September, booked 77 days in advance, depart on a Friday or Thursday and return on a Saturday

Cheap 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 June 12, 2025.

Round-trip from

$153
(Southwest)

One-way from

$70
(Southwest)

Popular in

February

Cheapest in

April

Average price

$270

Good round-trip deal

$253 or less

Good one-way deal

$149 or less
From Cleveland Hopkins Intl to Chicago (CHI)
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One-way flight from Cleveland Hopkins Intl to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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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).
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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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/12. 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 8/287:35 pmCLE - MDW
Nonstop1h 15mSouthwest
Sun 8/311:45 pmMDW - CLE
Nonstop1h 15mSouthwest
Deal found 6/12$153
This American Airlines deal was found by Cheapflights users on 6/10. 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 7/25:32 pmCLE - ORD
Nonstop1h 34mAmerican Airlines
Mon 8/410:10 pmORD - CLE
Nonstop1h 22mAmerican Airlines
Deal found 6/10$153
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Mon 8/47:30 pmCLE - ORD
Nonstop1h 39mUnited Airlines
Tue 8/57:33 amORD - CLE
Nonstop1h 26mUnited Airlines
Deal found 6/11$169
This Delta deal was found by Cheapflights users on 6/11. 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.
Mon 8/45:30 amCLE - ORD
1 stop3h 19mDelta
Mon 8/47:01 pmORD - CLE
1 stop3h 52mDelta
Deal found 6/11$177
This Southwest deal was found by Cheapflights users on 6/10. 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 11/136:00 amCLE - ORD
1 stop7h 15mSouthwest
Mon 11/171:45 pmORD - CLE
1 stop6h 20mSouthwest
Deal found 6/10$189
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/137:47 pmCLE - ORD
1 stop26h 43mSpirit Airlines
Sun 7/2011:11 amORD - CLE
1 stop26h 57mSpirit Airlines
Deal found 6/11$194
This Delta deal was found by Cheapflights users on 6/10. 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.
Thu 11/136:00 amCLE - MDW
1 stop4h 51mDelta
Mon 11/179:30 amMDW - CLE
1 stop4h 41mDelta
Deal found 6/10$208
This Frontier deal was found by Cheapflights users on 6/12. 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.
Mon 6/167:26 pmCLE - ORD
1 stop5h 48mFrontier
Tue 6/175:01 amORD - CLE
1 stop5h 29mFrontier
Deal found 6/12$228
This KAYAK deal was found by Cheapflights users on 6/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/196:25 pmCLE - MDW
1 stop5h 10mFrontier
Wed 7/2311:39 amMDW - CLE
1 stop5h 24mFrontier
Deal found 6/10$232
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/49:56 pmCLE - ORD
1 stop11h 11mMultiple Airlines
Mon 7/71:34 pmORD - CLE
1 stop4h 44mMultiple Airlines
Deal found 6/11$256
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/247:47 pmCLE - RFD
2 stops24h 32mMultiple Airlines
Thu 7/319:21 amRFD - CLE
1 stop8h 31mMultiple Airlines
Deal found 6/10$271

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 June 12, 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

Thu 8/28

7:35 pm-7:50 pm

Nonstop1h 15m

Chicago Midway

Sun 8/31

1:45 pm-4:00 pm

Nonstop1h 15m

$153

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Wed 7/2

5:32 pm-6:06 pm

Nonstop1h 34m

Chicago O'Hare Intl

Mon 8/4

10:10 pm-12:32 am

Nonstop1h 22m

$153

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Tue 9/9

5:35 am-11:50 am

1 stop7h 15m

Chicago O'Hare Intl

Sat 9/13

1:30 pm-10:05 pm

1 stop7h 35m

$155

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 8/4

6:00 am-6:29 am

Nonstop1h 29m

Chicago O'Hare Intl

Mon 8/4

7:35 pm-10:00 pm

Nonstop1h 25m

$169

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Mon 8/4

5:30 am-7:49 am

1 stop3h 19m

Chicago O'Hare Intl

Sat 8/9

7:10 am-1:29 pm

1 stop5h 19m

$177

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Sun 7/13

7:47 pm-9:30 pm

1 stop26h 43m

Chicago O'Hare Intl

Sun 7/20

11:11 am-3:08 pm

1 stop26h 57m

$194

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Thu 11/13

6:00 am-9:51 am

1 stop4h 51m

Chicago Midway

Mon 11/17

9:30 am-3:11 pm

1 stop4h 41m

$208

ClevelandChicago

CLE - MDW

CLEMDW

Cleveland Hopkins Intl

Sat 7/19

6:25 pm-10:35 pm

1 stop5h 10m

Chicago Midway

Wed 7/23

11:39 am-6:03 pm

1 stop5h 24m

$232

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Thu 6/26

7:25 am-4:58 pm

1 stop10h 33m

Chicago O'Hare Intl

Fri 6/27

6:16 pm-12:46 am

1 stop5h 30m

$238

ClevelandChicago

CLE - ORD

CLEORD

Cleveland Hopkins Intl

Fri 7/4

9:56 pm-8:07 am

1 stop11h 11m

Chicago O'Hare Intl

Mon 7/7

1:34 pm-7:18 pm

1 stop4h 44m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 25 results
1
2
3

The best insider tips for Cleveland to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
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.

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
Brandon Schultz

Brandon Schultz

Expert on Qatar Airways

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Marisa Garcia

Marisa Garcia

Expert on Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
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

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 June 9, 2025.

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?

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 June 12, 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 49% 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 June 8, 2025.

Travelers seeking maximum savings on their Cleveland to Chicago flight should consider departing on Friday 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

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 June 12, 2025.

The most flights from CLE to CHI are scheduled on a Monday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

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 June 12, 2025.
See what other customers who have flown with Alaska Airlines, Southwest and Delta from Cleveland to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Boarding

8.1

Comfort

7.8

Food

7.1

Overall

8.0

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 56 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 Southwest. Our recent data shows that you can find tickets from as low as $153 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $153 and $169 round-trip. Southwest 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 $70 on Southwest. Other airlines that offer cheap prices include American Airlines from $76 and United Airlines from $83 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 Copa Airlines (96%), SWISS (95%) or Cathay Pacific (93%) 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 $1,518, our data indicates the cheapest price to be $105. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $109.

  • 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

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$100Average$153FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$151Average$272FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$157Average$311FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$165Average$296FlexibilityNo cancel feeOn-time71%

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