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 $228 and $342 in January. The cheapest round-trip price found within the last 3 days was $165 on Frontier (Jan 9-Jan 11).

How long is the flight from Cleveland to Chicago?

Airlines like Delta, United Airlines, and Southwest fly from Cleveland to Chicago in about 1h 32m. The time it takes to get you to your destination can typically vary by up to 3h 53m. 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 Frontier. Our recent data shows that you can find tickets from as low as $108 on this airline. Additional options worth looking into are American Airlines and Southwest, starting at $138 and $141 round-trip. Frontier is currently priced 60% below the average price you’ll pay for this route.

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, November is the cheapest month in which you can book a flight from Cleveland to Chicago (average of $71). Flying from Cleveland to Chicago in January is currently the most expensive (average of $137). 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 day to fly from Cleveland to Chicago?

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 afternoons 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 (29 on average).

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 $1,082, our data indicates the cheapest price to be $112. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $151.

What are the most reliable airlines from Cleveland to Chicago?

Consider Cathay Pacific (95%), Copa Airlines (90%) or Qatar Airways (89%) 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 United Airlines, American Airlines or Southwest when booking your flight. These represent the most popular airlines when flying from Cleveland to Chicago.

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

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.

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 48 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.

$100+ Flights from Cleveland to Chicago

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$165 (Kiwi.com)
One-way from	$100 (Kiwi.com)
Popular in	December
Cheapest in	August
Average price	$279
Good round-trip deal	$312 or less
Good one-way deal	$205 or less

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust Score*3 stars
Priceline	Price Accuracy1 star	Trust Score*3 stars
Trip.com	Price Accuracy2 stars	Trust Score*3 stars
Cheapfaremart	Price Accuracy-	Trust Score*1 star

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.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$108	Average$166	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$138	Average$297	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$141	Average$283	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$157	Average$302	FlexibilityNo cancel fee	On-time69%

$100+ 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 1/25. 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

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Cheapflights Tip: The best prices from Cleveland Hopkins Intl to Chicago are usually found in August 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

Most accurate provider

Most trusted provider

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 November 4, 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 November 4, 2025.

Cheapflights Fare Finder

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

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 November.

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 October 31, 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 November 4, 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 November 2, 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 November 4, 2025.

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

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

Airports

CLE

ORD

MDW

Our travel experts

Reviews of airlines servicing Chicago

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.

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?

How long is the flight from Cleveland to Chicago?

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

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 Chicago?

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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

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 November 4, 2025.