CLE - CHI

$79 Find Cheap Flights from Cleveland to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Chicago departing on 9/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$163
Typical prices: $187-$338
Frontier
Wed 8/5Wed 8/12
CLE - ORD • 1 stop
Cheapest non-stop
$177
Typical prices: $169-$561
Southwest
Tue 8/4Tue 8/11
CLE - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
United Economy Plus adds up to 6 inches more legroom than standard economy.
American Basic Economy boards late; Southwest offers flexible changes.
Expert advice
Expert advice
Expert advice
Expert advice
Nonstop flights
Every day
You can fly direct with American Airlines, Southwest and United Airlines. Average duration is 1h 29m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
CLE
-
MDW
Cheapest • 13% average savings
CLE
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Detroit (DTW)
Cheapest • Avg $161 (round-trip)
Detroit (DTW)
Shortest trip • 3h 04m (one-way)
Insights
Insights
Insights
Insights
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 50% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
May
Cheapest • 18% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals

Cheap Flights from Cleveland to Chicago (CLE-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Chicago

Wed, Aug 5 - Wed, Aug 12
Frontier Logo
6:41 am - 7:53 pm
CLE
-
ORD
14h 12m
1 stop
Frontier Logo
7:05 am - 8:52 pm
ORD
-
CLE
12h 47m
1 stop
$163Frontier
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
6:40 am - 7:53 pm
CLE
-
ORD
14h 13m
1 stop
Frontier Logo
1:50 pm - 12:24 pm
ORD
-
CLE
21h 34m
1 stop
$164Frontier
Thu, Aug 6 - Tue, Aug 11
Frontier Logo
6:41 am - 7:53 pm
CLE
-
ORD
14h 12m
1 stop
Frontier Logo
1:50 pm - 12:24 pm
ORD
-
CLE
21h 34m
1 stop
$165Frontier
Tue, Aug 4 - Tue, Aug 11
United Airlines Logo
6:00 am - 6:40 am
CLE
-
ORD
1h 40mnonstop
United Airlines Logo
9:29 pm - 11:58 pm
ORD
-
CLE
1h 29mnonstop
$177United Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
5:15 am - 5:46 am
CLE
-
ORD
1h 31mnonstop
American Airlines Logo
9:24 pm - 11:55 pm
ORD
-
CLE
1h 31mnonstop
$178American Airlines
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
7:15 pm - 7:30 pm
CLE
-
MDW
1h 15mnonstop
Southwest Logo
1:00 pm - 3:10 pm
MDW
-
CLE
1h 10mnonstop
$179Southwest
Thu, Aug 6 - Thu, Aug 13
American Airlines Logo
8:44 pm - 9:30 pm
CLE
-
ORD
1h 46mnonstop
American Airlines Logo
6:40 am - 9:13 am
ORD
-
CLE
1h 33mnonstop
$179American Airlines
Sat, Oct 31 - Mon, Nov 2
Delta Logo
6:00 am - 9:18 am
CLE
-
MDW
4h 18m
1 stop
Delta Logo
6:45 pm - 11:52 pm
MDW
-
CLE
4h 07m
1 stop
$186Delta
Sat, Oct 31 - Mon, Nov 2
Delta Logo
2:20 pm - 4:24 pm
CLE
-
ORD
3h 04m
1 stop
Delta Logo
2:00 pm - 9:05 pm
ORD
-
CLE
6h 05m
1 stop
$186Delta
Thu, Aug 6 - Mon, Aug 10
Southwest Logo
7:15 pm - 7:30 pm
CLE
-
MDW
1h 15mnonstop
Southwest Logo
5:55 am - 12:35 pm
MDW
-
CLE
5h 40m
1 stop
$189Southwest
Booking Insights

KAYAK's insights & trends for Cleveland to Chicago flights

Get data-powered insights and trends into flights from Cleveland to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Cleveland to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Cleveland to Chicago departing in August.

What is the cheapest Cleveland to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Cleveland to Chicago costs $162 on the route between Cleveland (CLE) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 13% cheaper than other Cleveland-Chicago routes. The most popular route is between Cleveland (CLE) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Cleveland to Chicago?

The average price of all round-trip flights from Cleveland to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Cleveland to Chicago. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Cleveland to Chicago is May, where tickets cost $83 (return) on average. On the other hand, the most expensive months are February and June, where the average cost of round-trip tickets is $128 and $117 respectively.

Can I save money by flying with a layover from Cleveland to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $270, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Cleveland to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Cleveland to Chicago, you should book around 4 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

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Expert advice

Expert advice for your flight from Cleveland to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on ANA

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Jessica Macdonald

Jessica Macdonald

Expert on Lufthansa

Currently based in Scotland after living in South Africa and the United States, Jessica has been writing travel and aviation content for more than 10 years. She regularly contributes to Travel + Leisure and TripSavvy, and has had work published by Condé Nast Traveller and The Independent. She has traveled to more than 50 countries across six continents.

Read more
Duncan Madden

Duncan Madden

Expert on British Airways

Duncan is a freelance travel writer, copywriter and book author in constant search of travel stories and the perpetual sensation of being on holiday. He’s never happier than when on a dusty trail in search of empty waves or ducking under the piste tape in search of snowbound solitude. British born, living in Germany, but happiest heading for the horizon. His first book, Found in Translation, explores the etymologies and stories of country names around the world and is out now.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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
Brandon Schultz

Brandon Schultz

Expert on CLE

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

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds but there is an average 23% increase in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Cleveland to Chicago Midway Airport

When to book flights from Cleveland to Chicago

Are your dates flexible? Find out the best times to travel from Cleveland to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Cleveland to Chicago

  • How can I move between the terminals at Chicago Midway International Airport (MDW)?

    If you’ll be arriving at Chicago Midway International Airport (MDW) from CLE, there’s a road system linking the terminal and the secure area. You can easily move from one building to another via a pedestrian bridge after clearing with the security in the terminal building as you head to the concourse.

  • What are the family amenities at Chicago O'Hare International Airport (ORD)?

    Those arriving with kids at Chicago O’Hare International Airport (ORD) from CLE will find nursing suites for use at this property. You can locate them at the Rotunda in Terminal 3, and in Terminal 2, Concourse F. Also, they have sinks, chairs, and power sockets.

  • Which is the best way to get to downtown Chicago from MDW?

    Downtown Chicago is approximately 11 miles from MDW. There are numerous public transportation options linking the two points. However, the best way to travel between the two points is via the Orange Line train which covers the stretch in about 20-25min.

  • Are there car rentals from O'Hare International Airport (ORD)?

    Many rental car agencies are located at the O'Hare International Airport (ORD). From the arrival, head to Suite 830, or at Routes Car & Truck Rentals near Schiller Park to pick up your car. Book in advance to enjoy special rates.

  • What is the cheapest flight from Cleveland to Chicago?

    In the last 5 days, the lowest price for a flight from Cleveland to Chicago was $79 for a one-way ticket and $161 for a round-trip.

  • Do I need a passport to fly between Cleveland and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Cleveland to Chicago?

    When flying out of Cleveland you will be using Cleveland Hopkins Intl. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Cleveland to Chicago?

    American Airlines, JetBlue, and Delta offer inflight Wi-Fi service on the Cleveland to Chicago flight route.

  • Which aircraft models fly most regularly from Cleveland to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Cleveland to Chicago flight route.

  • Which airline alliances offer flights from Cleveland to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Cleveland and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Cleveland to Chicago?

    There are nonstop flights from Cleveland to Chicago on a daily basis.

  • Which is the best airline for flights from Cleveland to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Cleveland to Chicago are Southwest and United Airlines. With an average price for the route of $235 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $291 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Cleveland to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cleveland to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Cleveland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cleveland to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Cleveland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Cleveland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Cleveland to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $228 or less one-way and $334 or less round-trip.
  • Those traveling with kids via Cleveland Hopkins International Airport (CLE) should bear in mind that the facility offers designated suites for nursing and lactating moms. The rooms are centrally located across from B1 and provide privacy. Other amenities at this place include sinks, seats, and power sockets.
  • Cleveland Hopkins International Airport (CLE) has one Main Terminal with two levels and three Concourses: Concourses A, B, and C. There are walkways for travelers conveniently move from one terminal to the next. Plan to arrive at the airport early, at least 90min before departure for your bags to undergo a complete security screening.
  • Suppose you intend to fly out early in the morning via Cleveland Hopkins International Airport (CLE), consider sleeping in one of the various hotels that sit within easy reach of the airport. Typically, such facilities provide courtesy shuttles to and from the airport, enabling you to be at the airport just in time for your flight. Among the recommended hotels in this region are Sonesta Simply Suites Cleveland North Olmsted and Emerald Necklace Inn Bed and Breakfast.
  • If you need cash before you depart from CLE to Chicago, there are several ATMs to choose from. There are about nine Key Bank ATMs spread across this facility. For instance, in the Main Terminal, they’re adjacent to the south checkpoint, while in Concourse A they’re adjacent to Gate A-1.
  • Frontier Airlines allows passengers to bring their four-legged friends into the cabin. Such pets include cats, dogs, and rabbits. However, they must have valid health and vaccination certificates. Besides, you must restrain them in their lockers to prevent them from disturbing other passengers. Nevertheless, it might be helpful to check with the airline on their current pet policy.

Prefer to fly direct from Cleveland to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Cleveland Hopkins Intl to Chicago.
Find which airlines fly direct from Cleveland Hopkins Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Cleveland Hopkins Intl to Chicago

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Direct returns

Chicago to Cleveland Hopkins Intl

Monday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Tuesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

See more direct flights

Everything you need to know for your flight from Cleveland to Chicago

Information on your arrival and departure airports

Cleveland (CLE)