How long is the flight from Cleveland to Chicago?

Airlines like Frontier, Southwest, and United Airlines fly from Cleveland to Chicago in about 1h 15m. The time it takes to get you to your destination can typically vary by up to 8h 40m. 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 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, 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 day to fly from Cleveland to Chicago?

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

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).

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 $1,096, our data indicates the cheapest price to be $108. The most popular route (Cleveland Hopkins Intl - Chicago O'Hare Intl), is priced around $101.

What are the most reliable airlines from Cleveland to Chicago?

Consider Avianca (87%), ANA (79%) or Republic Airways (79%) 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 40% 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 260% 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 $288 1-2 weeks out and tickets from $663 for flights departing within the next 72 hours.

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

August can be a great time to fly to Chicago from Cleveland with a flight ticket averaging about $271. Cheapflights users have found deals in the month of August for as cheap as $111. The most expensive prices can be found in the month of February.

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 44% on your trip compared to booking a flight at noon.

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 53 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.

$76+ Flights from Cleveland to Chicago

Round-trip from	$139 (Kiwi.com)
One-way from	$76 (Southwest)
Popular in	February
Cheapest in	August
Average price	$273
Good round-trip deal	$236 or less
Good one-way deal	$163 or less

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$156	FlexibilityNo cancel fee	On-time62%
American Airlines	Cheapest$138	Average$296	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$141	Average$277	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$157	Average$311	FlexibilityNo cancel fee	On-time69%

$76+ 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 12/16. 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

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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 September 11, 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 September 11, 2025.

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The best insider tips for Cleveland to Chicago flights

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ORD

MDW

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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 August 29, 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 September 11, 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 September 7, 2025.

Weekly flight availability from Cleveland to Chicago

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?

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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 September 11, 2025.