Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Cleveland to Chicago from $54

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 4/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Cleveland to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Cleveland to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Cleveland to Chicago.

Cheap last minute flights

Planning a quick getaway from Cleveland to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Cleveland to Chicago

Find recent round-trip train or bus tickets from Cleveland to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
6:05 am - 2:11 pmCLE-ORD
9h 06m1 stop
4:41 pm - 12:28 amORD-CLE
6h 47m1 stop
$104Frontier
Find Deal
Mon, Feb 3 - Mon, Feb 3
6:15 am - 1:50 pmCLE-ORD
8h 35m1 stop
6:50 am - 3:33 pmORD-CLE
7h 43m1 stop
$108Frontier
Find Deal
Thu, Jan 30 - Thu, Feb 6
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
6:00 pm - 8:30 pmORD-CLE
1h 30mnonstop
$157American Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 22
10:34 am - 2:34 pmCLE-ORD
5h 00m1 stop
10:40 am - 1:01 pmORD-CLE
1h 21mnonstop
$167United Airlines
Find Deal
Tue, Feb 11 - Wed, Feb 19
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
8:35 pm - 10:59 pmORD-CLE
1h 24mnonstop
$172American Airlines
Find Deal
Wed, Jan 15 - Thu, Jan 16
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
11:25 am - 1:35 pmMDW-CLE
1h 10mnonstop
$172Southwest
Find Deal
Wed, Jan 15 - Sat, Jan 18
6:00 am - 9:55 amCLE-ORD
4h 55m1 stop
4:58 pm - 10:50 pmORD-CLE
4h 52m1 stop
$177Delta
Find Deal
Tue, Jan 21 - Wed, Jan 22
7:10 am - 11:59 amCLE-MDW
5h 49m1 stop
10:57 am - 6:23 pmMDW-CLE
6h 26m1 stop
$179Delta
Find Deal
Tue, Jan 21 - Wed, Jan 29
7:45 am - 8:05 amCLE-MDW
1h 20mnonstop
11:25 am - 1:35 pmMDW-CLE
1h 10mnonstop
$182Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 18
6:00 am - 9:44 amCLE-ORD
4h 44m1 stop
6:18 pm - 8:40 pmORD-CLE
1h 22mnonstop
$183United Airlines
Find Deal
Wed, Feb 12 - Wed, Feb 12
10:57 am - 5:49 pmCLE-MDW
7h 52m1 stop
$54Frontier
Find Deal
Thu, Apr 24
5:41 pm - 12:19 amCLE-ORD
7h 38m1 stop
$54Frontier
Find Deal
Mon, Apr 7
10:57 am - 11:36 amCLE-ORD
1h 39mnonstop
$79United Airlines
Find Deal
Tue, Feb 4
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
$79Southwest
Find Deal
Tue, Mar 4
11:01 am - 5:43 pmCLE-MDW
7h 42m1 stop
$89Delta
Find Deal
Tue, Feb 11
2:15 pm - 4:13 pmCLE-ORD
2h 58m1 stop
$89Delta
Find Deal
Tue, Feb 4
7:00 am - 7:39 amCLE-ORD
1h 39mnonstop
$94United Airlines
Find Deal
Mon, Feb 10
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
$94Southwest
Find Deal
Mon, Feb 3
10:39 am - 11:15 amCLE-ORD
1h 36mnonstop
$149American Airlines
Find Deal
Thu, May 8
1:02 pm - 1:36 pmCLE-ORD
1h 34mnonstop
$169American Airlines
Find Deal
Fri, Mar 14
9:59 pm - 9:29 amCLE-ORD
12h 30m1 stop
5:02 pm - 12:13 amORD-CLE
6h 11m1 stop
$249Frontier
Find Deal
Wed, Jan 8 - Thu, Jan 9
6:46 pm - 11:14 pmCLE-MDW
5h 28m1 stop
7:45 am - 7:42 pmMDW-CLE
10h 57m1 stop
$279Frontier
Find Deal
Mon, Jan 6 - Mon, Jan 13
6:40 pm - 7:33 pmCLE-ORD
1h 53mnonstop
8:55 pm - 9:37 amORD-CLE
11h 42m1 stop
$299American Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 4
7:48 pm - 2:00 pmCLE-ORD
19h 12m1 stop
5:50 pm - 8:12 pmORD-CLE
1h 22mnonstop
$419United Airlines
Find Deal
Sat, Jan 4 - Sun, Jan 5
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
6:00 pm - 8:30 pmORD-CLE
1h 30mnonstop
$491American Airlines
Find Deal
Wed, Jan 8 - Thu, Jan 9
7:05 am - 7:35 amCLE-MDW
1h 30mnonstop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$491Southwest
Find Deal
Wed, Jan 8 - Thu, Jan 9
6:15 am - 12:30 pmCLE-MDW
7h 15m1 stop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$501Southwest
Find Deal
Wed, Jan 8 - Thu, Jan 9
7:05 am - 12:46 pmCLE-MDW
6h 41m1 stop
6:00 am - 12:32 pmMDW-CLE
5h 32m1 stop
$597Delta
Find Deal
Tue, Jan 7 - Fri, Jan 10
10:28 am - 1:08 pmCLE-MDW
3h 40m1 stop
6:00 am - 12:32 pmMDW-CLE
5h 32m1 stop
$599Delta
Find Deal
Tue, Jan 7 - Fri, Jan 10
6:03 pm - 6:42 pmCLE-ORD
1h 39mnonstop
2:32 pm - 4:57 pmORD-CLE
1h 25mnonstop
$663United Airlines
Find Deal
Sat, Jan 4 - Sun, Jan 5
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
6:00 pm - 8:30 pmORD-CLE
1h 30mnonstop
$157American Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 22
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
11:25 am - 1:35 pmMDW-CLE
1h 10mnonstop
$172Southwest
Find Deal
Wed, Jan 15 - Sat, Jan 18
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
8:35 pm - 10:59 pmORD-CLE
1h 24mnonstop
$172American Airlines
Find Deal
Wed, Jan 15 - Thu, Jan 16
11:06 am - 11:40 amCLE-ORD
1h 34mnonstop
8:35 pm - 10:59 pmORD-CLE
1h 24mnonstop
$173American Airlines
Find Deal
Sat, Feb 1 - Tue, Feb 11
7:45 am - 8:05 amCLE-MDW
1h 20mnonstop
11:25 am - 1:35 pmMDW-CLE
1h 10mnonstop
$182Southwest
Find Deal
Sat, Jan 18 - Sat, Jan 18
10:57 am - 11:36 amCLE-ORD
1h 39mnonstop
2:32 pm - 4:54 pmORD-CLE
1h 22mnonstop
$187United Airlines
Find Deal
Thu, Jan 30 - Thu, Feb 6
11:40 am - 12:05 pmCLE-MDW
1h 25mnonstop
6:20 pm - 8:35 pmMDW-CLE
1h 15mnonstop
$187Southwest
Find Deal
Thu, Jan 16 - Mon, Jan 20
2:15 pm - 2:54 pmCLE-ORD
1h 39mnonstop
9:35 pm - 11:59 pmORD-CLE
1h 24mnonstop
$201United Airlines
Find Deal
Tue, Jan 28 - Fri, Jan 31
9:00 am - 9:39 amCLE-ORD
1h 39mnonstop
7:45 pm - 10:15 pmORD-CLE
1h 30mnonstop
$216United Airlines
Find Deal
Mon, Jan 20 - Fri, Jan 24
10:57 am - 11:36 amCLE-ORD
1h 39mnonstop
9:35 pm - 11:59 pmORD-CLE
1h 24mnonstop
$232United Airlines
Find Deal
Sat, Jan 18 - Wed, Jan 22

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets
Frontier
Feb 3
CLE6:05 amCleveland Hopkins Intl
9h 06m
1 stop
ORD2:11 pmChicago O'Hare Intl
Feb 3
ORD4:41 pmChicago O'Hare Intl
6h 47m
1 stop
CLE12:28 amCleveland Hopkins Intl
Frontier
Jan 30
CLE6:15 amCleveland Hopkins Intl
8h 35m
1 stop
ORD1:50 pmChicago O'Hare Intl
Feb 6
ORD6:50 amChicago O'Hare Intl
7h 43m
1 stop
CLE3:33 pmCleveland Hopkins Intl
Frontier
Mar 6
CLE10:50 amCleveland Hopkins Intl
7h 36m
1 stop
ORD5:26 pmChicago O'Hare Intl
Mar 10
ORD8:50 amChicago O'Hare Intl
6h 40m
1 stop
CLE4:30 pmCleveland Hopkins Intl

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets
American Airlines
Jan 21
CLE6:40 amCleveland Hopkins Intl
1h 39m
ORD7:19 amChicago O'Hare Intl
Jan 22
ORD6:00 pmChicago O'Hare Intl
1h 30m
CLE8:30 pmCleveland Hopkins Intl
American Airlines
Jan 15
CLE6:40 amCleveland Hopkins Intl
1h 39m
ORD7:19 amChicago O'Hare Intl
Jan 16
ORD8:35 pmChicago O'Hare Intl
1h 24m
CLE10:59 pmCleveland Hopkins Intl
American Airlines
Feb 1
CLE11:06 amCleveland Hopkins Intl
1h 34m
ORD11:40 amChicago O'Hare Intl
Feb 11
ORD8:35 pmChicago O'Hare Intl
1h 24m
CLE10:59 pmCleveland Hopkins Intl

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?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $225. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Cleveland to Chicago during April average around $232.

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 Saturday when prices can be found for as low as $227. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Cleveland to Chicago for around $298.

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 evening. Flights from Cleveland to Chicago during this time can be as low as $258. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $297.

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 to Chicago?

The best time to book a flight to Chicago from Cleveland is 56 days out, which is when prices tend to be around $289. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $153.

What cabin class options are available on Cleveland Hopkins Intl to Chicago flights?

There are 4 cabin classes available to choose from on Cleveland Hopkins Intl 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?

You could potentially save up to 31% on your flight if you consider stops on a Cleveland to Chicago flight.

How have Cleveland to Chicago flight prices changed over time?

As of January 2025, prices for Cleveland to Chicago flights are approximately 0% more expensive when compared to flights at the same time last year.

When to book flights from Cleveland to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Cleveland to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

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

Best Price Found

$54

Fastest flight time

1h 15m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cleveland in the past 72 hours is $54. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $104.
The fastest flight from Cleveland to Chicago takes 1h 15m
Direct flights go from Cleveland to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • Is flying the fastest way to get from Cleveland to Chicago?

    The quickest way to travel this route is to take a flight from Cleveland to Chicago, doing so can potentially save up to 7h 35m of travel time. While these options may take longer, booking a train from Cleveland to Chicago or a bus from Cleveland to Chicago may suit your needs if travel time is less of a factor in your decision making.

  • Is flying the cheapest way to get from Cleveland to Chicago?

    Expect a bus to be one of the cheapest options available to you for travel. Currently, a bus has deals available from $81. While they may not be the most cost-effective options currently available a flight from Cleveland to Chicago or a train from Cleveland to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

  • 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?

  • 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?

  • What is the most popular airline from Cleveland to Chicago?


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
FrontierPriceFrom $100Free CancellationRating
6.1
3,452 reviews
Search Frontier flights
American AirlinesPriceFrom $110Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $136Free CancellationRating
7.4
8,965 reviews
Search United Airlines flights
DeltaPriceFrom $156Free CancellationRating
8.0
8,527 reviews
Search Delta flights
SouthwestPriceFrom $168Free CancellationRating
8.1
4,688 reviews
Search Southwest flights
  • Southwest Flights From Cleveland to Chicago

    Southwest flight deals from Cleveland to Chicago start from $168 round-trip. Over the 12 Southwest flights for this route in a normal week, average airfare is usually $280 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 8,966 reviews) operates around 12 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $317, with deals from around $136 rare but found on momondo. Referenced prices are for round-trip Cleveland to Chicago flight searches in the last 72 hours.


Why 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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Wed 1/8
Wed 1/15
Email me momondo's favorite deals

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago