Cheap flights from Chicago to Cleveland from $85
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Cleveland departing on 11/26. 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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Fly from
Fly to
Route
Depart
Return
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Tue 11/10
6:42 pm-12:07 pm
1 stop16h 25m
Cleveland Hopkins Intl
Fri 11/13
3:21 pm-11:47 pm
1 stop9h 26m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Tue 11/10
9:51 am-9:06 am
1 stop22h 15m
Cleveland Hopkins Intl
Wed 11/11
1:12 pm-8:46 am
1 stop20h 34m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Thu 11/5
6:30 am-12:45 pm
1 stop5h 15m
Cleveland Hopkins Intl
Mon 11/9
5:35 pm-11:15 pm
1 stop6h 40m
ChicagoCleveland
MDW Chicago Midway - CLE Cleveland Hopkins Intl
MDWCLE
Chicago Midway
Fri 11/6
6:10 pm-11:50 pm
1 stop4h 40m
Cleveland Hopkins Intl
Fri 11/13
8:55 pm-12:10 am
1 stop4h 15m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Fri 11/6
8:29 am-3:42 pm
1 stop6h 13m
Cleveland Hopkins Intl
Fri 11/13
2:13 pm-6:30 pm
1 stop5h 17m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Thu 11/5
7:00 am-1:39 pm
1 stop5h 39m
Cleveland Hopkins Intl
Mon 11/9
4:00 pm-8:17 pm
1 stop5h 17m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Sat 11/21
9:30 am-12:05 pm
Nonstop1h 35m
Cleveland Hopkins Intl
Sun 11/22
4:59 pm-6:00 pm
Nonstop2h 01m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Tue 12/22
10:05 pm-12:44 am
Nonstop1h 39m
Cleveland Hopkins Intl
Fri 12/25
7:20 am-8:12 am
Nonstop1h 52m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Sat 11/7
7:15 am-9:41 am
Nonstop1h 26m
Cleveland Hopkins Intl
Sun 11/8
5:55 pm-6:35 pm
Nonstop1h 40m
ChicagoCleveland
ORD Chicago O'Hare Intl - CLE Cleveland Hopkins Intl
ORDCLE
Chicago O'Hare Intl
Thu 11/5
9:36 pm-11:59 pm
Nonstop1h 23m
Cleveland Hopkins Intl
Sun 11/8
6:12 am-6:50 am
Nonstop1h 38m
See travel insights to Cleveland from
How to get the cheapest flight ticket from Chicago to Cleveland
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 Chicago and Cleveland?
Prices are currently low for flights on this route.
Typical prices usually range from $222 to $489.The lowest price recently found on this route was $129.
What is the cheapest month to fly to Cleveland?
In general, December is the cheapest month to fly from Chicago to Cleveland. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $298. If you’re not able to fly to Cleveland in December, then November is your next best option. Flight prices from Chicago to Cleveland during November average around $323.
What is the cheapest day to depart on your flight to Cleveland?
The cheapest day to depart from Chicago to Cleveland is on a Saturday when prices can be found for as low as $266. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Cleveland on Sunday is $534.
What is the cheapest time of day to depart on your flight to Cleveland?
Our data shows that the cheapest Chicago to Cleveland flights are usually those with departure times at noon. Our users have found flights to Cleveland at noon for as low as $312. In contrast, the most expensive time of day to depart to Cleveland is in the evening when prices are around $472.
What is the cheapest Chicago to Cleveland Hopkins Intl flight route?
Fly from Chicago Midway to Cleveland Hopkins Intl for the best Chicago - Cleveland Hopkins Intl flight prices
How far in advance should I book a flight from Chicago to Cleveland?
You are more likely to see cheaper flights to Cleveland from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Cleveland for around $422 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cleveland from Chicago for as low as $118 on momondo.
What cabin class options are available on Chicago to Cleveland flights?
There are 4 cabin classes available to choose from on Chicago to Cleveland 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 Chicago to Cleveland flights?
You could potentially save up to 1% on your flight if you consider stops on a Chicago to Cleveland flight.
How have Chicago to Cleveland flight prices changed over time?
As of October 2026, prices for Chicago to Cleveland flights are approximately 12% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to Cleveland Hopkins Intl?
Southwest, United Airlines, and Frontier are the most popular carriers operating from Chicago to Cleveland Hopkins Intl
What airlines fly to Cleveland?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Cleveland from Chicago according to our data. United Airlines is the first choice among our users, with 68% of people opting to fly with this airline when traveling to Cleveland. Keep in mind that there are 6 different airlines that fly to Cleveland on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Cleveland on average per day?
As of October 2026, 54 flights take off from Chicago and land in Cleveland each day. The most common flight departure time for this route is 9:00PM, with 35% of daily flights taking off in the afternoon.
How many flights depart from Chicago to Cleveland on average per week?
As of October 2026, there are 381 flights per week flying from Chicago to Cleveland. The most common day of the week flights depart is Wed, with 17% of flights taking off on this day.
When to book flights from Chicago to Cleveland
Cheap Chicago to Cleveland (CHI to CLE) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Cleveland
Frequently asked questions about flying from Chicago to Cleveland
How far is Chicago to Cleveland Hopkins Intl by plane?
A flight from Chicago to Cleveland Hopkins Intl will travel around 307.0 mi. In terms of flight time, this usually takes a little over 1h 10m.
When did momondo last update prices for flights from Chicago to Cleveland Hopkins Intl Airport?
Prices for flights from Chicago to Cleveland Hopkins Intl Airport are updated daily.
How many operators does momondo search for flights from Chicago to Cleveland Hopkins Intl Airport?
There are 5 operators available for flights from Chicago to Cleveland Hopkins Intl Airport as of October 2026.
How old do you have to be to fly from Chicago to Cleveland Hopkins Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cleveland Hopkins Intl Airport.
What documentation or ID do you need to fly to Cleveland Hopkins Intl Airport?
The necessary travel and health documents for your Cleveland Hopkins Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Cleveland?
Based on momondo bookings for flights between Chicago and Cleveland, the leading plane model is Boeing 737-800, making up 13.10% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 12.42%, Boeing 737-900 with 10.64%, and Boeing 737 MAX 8 with 9.40%.
What is the most popular airline from Chicago to Cleveland?
Based on momondo bookings for flights between Chicago and Cleveland, the leading airline is United Airlines, making up 60% of the total bookings. Other popular airlines include American Airlines with 21% and Southwest with 19%.
Best airlines flying from Chicago to Cleveland
Compare and see reviews for airlines that fly from Chicago to Cleveland with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $97 | Free Cancellation | Rating 7.1 3,048 reviews | |||
| PriceFrom $111 | Free Cancellation | Rating 7.0 12,146 reviews | |||
| PriceFrom $117 | Free Cancellation | Rating 7.9 4,223 reviews | |||
| PriceFrom $134 | Free Cancellation | Rating 5.6 2,550 reviews | |||
| PriceFrom $147 | Free Cancellation | Rating 7.4 10,319 reviews |
Southwest Flights From Chicago to Cleveland
Across 15 Southwest flights from Chicago to Cleveland this week, the average price was $509, with the best Southwest deals starting from $117 round-trip. 4,223 users have rated Southwest on momondo, with an average score of 7.9/10.
United Airlines Flights From Chicago to Cleveland
Across 10,319 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Chicago to Cleveland about 51 times each week, with ticket deals ranging from $147 to $455. Price data is based on momondo searches in the last 72 hours.
Traveling to a place near Cleveland?
Book flights to Cleveland if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to Cleveland?
momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Cleveland. Millions of users trust and use momondo every year so you are in good hands.
Can I find flights from Chicago to Cleveland with flexible booking policies on momondo?
Flights from Chicago to Cleveland with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to Cleveland?
Once you have performed a search for Chicago to Cleveland 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 Chicago to Cleveland right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Chicago to Cleveland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Cleveland and let you know when they change.