Cheap flights from Cleveland to Chicago from $59
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Chicago departing on 11/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Frontier flights from Cleveland to Chicago O'Hare Intl Airport
Our best Frontier deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
United Airlines flights from Cleveland to Chicago O'Hare Intl Airport
Our best United Airlines deals on Cleveland to Chicago O'Hare Intl Airport flight tickets
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Use the filters below to find and compare flights from Cleveland to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Tue 12/1
12:57 pm-7:15 am
1 stop19h 18m
Chicago O'Hare Intl
Thu 12/3
10:37 pm-12:55 am
1 stop25h 18m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Sat 12/5
12:57 pm-6:37 pm
1 stop6h 40m
Chicago O'Hare Intl
Mon 12/7
8:00 am-12:37 am
1 stop15h 37m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Wed 12/9
12:57 pm-7:20 am
1 stop19h 23m
Chicago O'Hare Intl
Thu 12/10
10:37 pm-11:34 am
1 stop11h 57m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Fri 11/27
7:00 am-7:40 am
Nonstop1h 40m
Chicago O'Hare Intl
Fri 11/27
1:00 pm-3:28 pm
Nonstop1h 28m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Sat 10/31
10:23 am-11:10 am
Nonstop1h 47m
Chicago O'Hare Intl
Mon 11/2
7:20 pm-9:55 pm
Nonstop1h 35m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Sat 10/31
9:21 pm-10:05 pm
Nonstop1h 44m
Chicago O'Hare Intl
Mon 11/2
6:59 am-9:32 am
Nonstop1h 33m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Fri 1/22
2:05 pm-6:40 pm
1 stop5h 35m
Chicago O'Hare Intl
Wed 1/27
7:00 am-1:35 pm
1 stop5h 35m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Mon 11/9
2:13 pm-6:30 pm
1 stop5h 17m
Chicago O'Hare Intl
Thu 11/12
8:29 am-1:28 pm
1 stop3h 59m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Sat 11/7
5:55 pm-6:35 pm
Nonstop1h 40m
Chicago O'Hare Intl
Sun 11/8
2:21 pm-4:49 pm
Nonstop1h 28m
ClevelandChicago
CLE Cleveland Hopkins Intl - ORD Chicago O'Hare Intl
CLEORD
Cleveland Hopkins Intl
Thu 11/12
10:49 am-11:29 am
Nonstop1h 40m
Chicago O'Hare Intl
Sun 11/15
7:49 pm-10:15 pm
Nonstop1h 26m
See travel insights to Chicago from
How to get the cheapest flight ticket from Cleveland to Chicago O'Hare Intl Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Cleveland and Chicago O'Hare Intl Airport?
Prices are currently low for flights on this route.
Typical prices usually range from $239 to $392.The lowest price recently found on this route was $124.
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of December is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cleveland averaging around $277.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $474. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Cleveland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $674.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Cleveland in the morning is the least expensive time of day to depart. momondo users have found prices as low as $488 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $869. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Cleveland Hopkins Intl to Chicago O'Hare Intl flight route?
Fly from Cleveland Hopkins Intl to Chicago O'Hare Intl for the best Cleveland Hopkins Intl - Chicago O'Hare Intl flight prices
How far in advance should I book a flight from Cleveland to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $323 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Cleveland for as low as $198 on momondo.
What cabin class options are available on Cleveland to Chicago O'Hare Intl Airport flights?
There are 4 cabin classes available to choose from on Cleveland to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Cleveland to Chicago O'Hare Intl Airport flights?
No. A direct flight is the cheapest option for a flight between Cleveland to Chicago O'Hare Intl Airport.
How have Cleveland to Chicago O'Hare Intl Airport flight prices changed over time?
As of October 2026, prices for Cleveland to Chicago O'Hare Intl Airport flights are approximately 26% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Cleveland Hopkins Intl to Chicago O'Hare Intl?
United Airlines and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Cleveland according to our data. United Airlines is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 4 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Cleveland to Chicago O'Hare Intl Airport on average per day?
As of October 2026, there are 62 flights per day flying from Cleveland to Chicago O'Hare Intl Airport. The most common time of day flights depart is 12:00PM, with 44% of flights taking off in the afternoon.
How many flights depart from Cleveland to Chicago O'Hare Intl Airport on average per week?
As of October 2026, 436 flights take off from Cleveland and land in Chicago O'Hare Intl Airport each week. The most common flight departure day for this route is Fri, with 16% of weekly flights taking off on this day.
When to book flights from Cleveland to Chicago O'Hare Intl Airport
Cheap Cleveland to Chicago O'Hare Intl Airport (CLE to ORD) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago O'Hare Intl Airport
Frequently asked questions about flying from Cleveland to Chicago O'Hare Intl Airport
How far is Cleveland Hopkins Intl to Chicago O'Hare Intl by plane?
Cleveland Hopkins Intl and Chicago O'Hare Intl are 321.6 mi apart from one another. 1h 28m is a normal flight duration for this route.
When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?
Prices for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport were last updated today.
How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?
As of October 2026, there are 3 operators available to choose from for flights from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Cleveland to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Cleveland and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737-800, making up 11.84% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 9.99%, Boeing 737-900 with 8.24%, and Embraer 175 with 8.14%.
What is the most popular airline from Cleveland to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Cleveland to Chicago O'Hare Intl Airport is United Airlines (73% of total bookings). The next most popular airlines are American Airlines (25%) and Frontier (1%).
Best airlines flying from Cleveland to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Cleveland to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $117 | Free Cancellation | Rating 7.0 12,155 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.4 10,351 reviews | |||
| PriceFrom $146 | Free Cancellation | Rating 5.5 2,541 reviews |
United Airlines Flights From Cleveland to Chicago O'Hare Intl Airport
United Airlines flight deals from Cleveland to Chicago O'Hare Intl Airport start from $138 round-trip. Over the 59 United Airlines flights for this route in a normal week, average airfare is usually $326 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Cleveland to Chicago O'Hare Intl Airport
Across 12,155 American Airlines reviews on momondo, the average score is 7.0/10. American Airlines flies from Cleveland to Chicago O'Hare Intl Airport about 37 times each week, with ticket deals ranging from $117 to $270. Price data is based on momondo searches in the last 72 hours.
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Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Cleveland to Chicago?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Cleveland to Chicago. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Cleveland to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Cleveland on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Cleveland to Chicago?
Once you have performed a search for Cleveland to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from Cleveland to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Cleveland. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.