S$174 Cheap Flights from Cleveland to Chicago

View S$174 flight on Thu, 25 Dec, 2025Opens in a new window

Popular airlines from Cleveland Hopkins International Airport (CLE) to Chicago

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Cheap Flights from Cleveland to Chicago (CLE-CHI)

Prices were available within the past 7 days and start at S$174 for one-way flights and S$683 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$683 Return, found 17 hours ago
S$683
Return
found 17 hours ago
Select United flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$683 found 17 hours ago
American Airlines
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$687 Return, found 17 hours ago
S$687
Return
found 17 hours ago
Select American Airlines flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$687 found 17 hours ago
United
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$694 Return, found 17 hours ago
S$694
Return
found 17 hours ago
Select United flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$694 found 17 hours ago
American Airlines
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$695 Return, found 17 hours ago
S$695
Return
found 17 hours ago
Select American Airlines flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$695 found 17 hours ago
American Airlines
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$696 Return, found 17 hours ago
S$696
Return
found 17 hours ago
Select American Airlines flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$696 found 17 hours ago
American Airlines
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$699 Return, found 17 hours ago
S$699
Return
found 17 hours ago
Select American Airlines flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$699 found 17 hours ago
Delta
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$708 Return, found 17 hours ago
S$708
Return
found 17 hours ago
Select Delta flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$708 found 17 hours ago
Delta
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$712 Return, found 17 hours ago
S$712
Return
found 17 hours ago
Select Delta flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$712 found 17 hours ago
Delta
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
MDW
Chicago
S$712 Return, found 17 hours ago
S$712
Return
found 17 hours ago
Select Delta flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$712 found 17 hours ago
American Airlines
Sun, 14 Dec - Mon, 15 Dec
CLE
Cleveland
ORD
Chicago
S$726 Return, found 17 hours ago
S$726
Return
found 17 hours ago
Select American Airlines flight, departing Sun, 14 Dec from Cleveland to Chicago, returning Mon, 15 Dec, priced at S$726 found 17 hours ago

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Find the cheapest month to fly from Cleveland (CLE) to Chicago (CHI)

August is typically the cheapest month to fly

From S$119 - S$371 per traveller.
Cleveland to Chicago route information
Origin airport
Hopkins Intl.
Destination airport
O'Hare Intl.
Return price
S$683
Distance
504 km

Perfect flights from Cleveland to Chicago

Your Journey from Cleveland to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Cleveland to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including United, American Airlines, Delta. Our selection of flights from Hopkins Intl. to CHI-All Airports caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Cleveland to Chicago Flights

Experience the joy of finding cheap flights from Hopkins Intl. to CHI-All Airports that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$174 and roundtrip prices from S$683*.
 

Pre-Flight Essentials

Ensure a smooth journey from Cleveland to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Cleveland to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Cleveland to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Cleveland to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Cleveland to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Hopkins Intl. Airport (CLE) to Chicago, IL (CHI-All Airports)?
The lowest price advertised for a round-trip journey between CLE and Chicago, IL (CHI-All Airports) is S$683. But you better get a move on. This figure is taken from fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Cleveland Hopkins Intl. Airport to Chicago, IL (CHI-All Airports)?
Most flights can be cancelled online, but each airline has its own set of terms and conditions. If you do need to cancel your flight, visit our Customer Service Portal and follow the instructions.
How do I find cheap flights from Cleveland Hopkins Intl. Airport to Chicago, IL (CHI-All Airports) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for CLE to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from CLE to Chicago, IL (CHI-All Airports)?
The flight distance from CLE (CLE) to Chicago, IL (CHI-All Airports) (CHI) is just 570 kilometres. You'll be disembarking the plane and picking up your bags from the carousel in no time.
Which airlines fly direct from Cleveland Hopkins Intl. Airport to Chicago, IL (CHI-All Airports)?
United Airlines (UA) is a top option. It offers 152 flights between Hopkins Intl. Airport (CLE) and Chicago, IL (CHI-All Airports) each month. If you're eager for more options, check out the ticket prices from Southwest Airlines (WN). This carrier operates 134 flights monthly between these airports.
Are CLE to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally nab a bargain, with some of the cheapest airfares from CLE to Chicago, IL (CHI-All Airports) popping up a few weeks before the departure date. If you'd rather plan ahead of time, Expedia compares and updates the best flight deals frequently — as early as a year in advance in some cases. It depends on the carrier though, as not all airlines release prices so far in advance.

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