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 12/18. 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
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 - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 11/14
3:21 pm-11:47 pm
1 stop9h 26m
Chicago Midway
Mon 11/16
6:42 pm-12:07 pm
1 stop16h 25m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Sat 11/7
8:35 am-9:00 am
Nonstop1h 25m
Chicago Midway
Wed 11/11
6:00 am-12:00 pm
1 stop5h 00m
ClevelandChicago
CLE Cleveland Hopkins Intl - MDW Chicago Midway
CLEMDW
Cleveland Hopkins Intl
Wed 11/4
12:40 pm-4:15 pm
1 stop4h 35m
Chicago Midway
Sat 11/7
8:00 am-10:20 am
Nonstop1h 20m
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
See travel insights to Chicago from
How to get the cheapest flight ticket from Cleveland to Chicago
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?
Prices are currently low for flights on this route.
Typical prices usually range from $205 to $318.The lowest price recently found on this route was $124.
What is the cheapest month to fly to Chicago?
The month of May is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $251. If you’re not able to fly to Chicago in May, then April is your next best option. Flight prices from Cleveland to Chicago during April average around $266.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $458. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $630.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Cleveland to Chicago during this time can be as low as $478. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $726.
What is the cheapest Cleveland Hopkins Intl to Chicago flight route?
Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland Hopkins Intl - Chicago flight prices
How far in advance should I book a flight from Cleveland to Chicago?
You are more likely to see cheaper flights to Chicago from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago 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 from Cleveland for as low as $198 on momondo.
What cabin class options are available on Cleveland to Chicago flights?
There are 4 cabin classes available to choose from on Cleveland to Chicago 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 flights?
No. A direct flight is the cheapest option for a flight between Cleveland to Chicago.
How have Cleveland to Chicago flight prices changed over time?
As of October 2026, prices for Cleveland to Chicago flights are approximately 39% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Cleveland Hopkins Intl to Chicago?
Southwest, United Airlines, and Delta are the most popular carriers operating from Cleveland Hopkins Intl to Chicago
What airlines fly to Chicago?
United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Chicago from Cleveland according to our data. United Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Cleveland to Chicago on average per day?
The number of flights available between Cleveland and Chicago is 64 per day as of October 2026. The most frequent departure time is 12:00PM, with 44% of daily flights leaving in the afternoon.
How many flights depart from Cleveland to Chicago on average per week?
The number of flights available between Cleveland and Chicago is 450 per week as of October 2026. The most frequent departure day is Fri, with 16% of weekly flights leaving on this day.
When to book flights from Cleveland to Chicago
Cheap Cleveland to Chicago (CLE to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Cleveland to Chicago
Frequently asked questions about flying from Cleveland to Chicago
How far is Cleveland Hopkins Intl to Chicago by plane?
Cleveland Hopkins Intl and Chicago are 307.0 mi apart from one another. A reasonable flight in good conditions will take 1h 15m.
When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Chicago?
Prices for flights from Cleveland Hopkins Intl Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Chicago?
As of October 2026, there are 4 operators available to choose from for flights from Cleveland Hopkins Intl Airport to Chicago.
How old do you have to be to fly from Cleveland Hopkins Intl Airport to Chicago?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Cleveland Hopkins Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The necessary travel and health documents for your Chicago 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 Cleveland to Chicago?
momondo data reveals that the most frequently booked plane model on the route from Cleveland to Chicago is Boeing 737-800, representing 11.48% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 9.34%, Boeing 737 MAX 8 at 8.88%, and Boeing 737-700 at 7.95%.
What is the most popular airline from Cleveland to Chicago?
momondo data reveals that the most frequently booked airline on the route from Cleveland to Chicago is United Airlines, representing 51% of all bookings. The subsequent popular airlines are Southwest at 28%, American Airlines at 19%, and Frontier at 2%.
Best airlines flying from Cleveland to Chicago
Compare and see reviews for airlines that fly from Cleveland to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $117 | Free Cancellation | Rating 7.9 4,218 reviews | |||
| PriceFrom $117 | Free Cancellation | Rating 7.0 12,155 reviews | |||
| PriceFrom $138 | Free Cancellation | Rating 7.4 10,350 reviews | |||
| PriceFrom $146 | Free Cancellation | Rating 5.5 2,541 reviews |
Southwest Flights From Cleveland to Chicago
Southwest flight deals from Cleveland to Chicago start from $117 round-trip. Over the 14 Southwest flights for this route in a normal week, average airfare is usually $260 round-trip - but some users have found much cheaper deals with momondo.
United Airlines Flights From Cleveland to Chicago
United Airlines (7.4/10 from 10,350 reviews) operates around 59 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $326, with deals from around $138 rare but found on momondo. Referenced prices are for round-trip Cleveland to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
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 collates all your flight options in one place and lets you filter them to find the perfect flight from Cleveland to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Cleveland to Chicago with flexible booking policies on momondo?
All flight searches from Cleveland to Chicago on momondo can be filtered to show those which offer flexible booking policies.
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 can track prices for Cleveland to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.