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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 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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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.
6:30 am - 11:41 amCLE-MDW
6h 11m1 stop
6:49 pm - 7:40 amMDW-CLE
11h 51m1 stop
$108Frontier
Find Deal
Mon, Dec 16 - Tue, Dec 17
6:15 am - 1:50 pmCLE-ORD
8h 35m1 stop
3:16 pm - 11:52 pmORD-CLE
7h 36m1 stop
$108Frontier
Find Deal
Thu, Jan 16 - Mon, Jan 20
6:00 am - 6:35 amCLE-ORD
1h 35mnonstop
12:53 pm - 3:17 pmORD-CLE
1h 24mnonstop
$157United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 17
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$158Southwest
Find Deal
Tue, Dec 31 - Tue, Jan 7
11:00 am - 11:31 amCLE-ORD
1h 31mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$162United Airlines
Find Deal
Wed, Dec 11 - Sat, Dec 14
6:10 am - 6:35 amCLE-MDW
1h 25mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$163Southwest
Find Deal
Sat, Dec 14 - Tue, Dec 17
6:00 am - 1:00 pmCLE-ORD
8h 00m2 stops
5:25 pm - 11:00 pmORD-CLE
4h 35m1 stop
$181Delta
Find Deal
Tue, Dec 17 - Tue, Dec 17
6:00 am - 1:00 pmCLE-ORD
8h 00m2 stops
8:35 am - 1:57 pmORD-CLE
4h 22m1 stop
$186Delta
Find Deal
Sat, Dec 14 - Tue, Dec 17
6:27 am - 7:09 amCLE-ORD
1h 42mnonstop
8:34 pm - 11:10 pmORD-CLE
1h 36mnonstop
$207American Airlines
Find Deal
Mon, Dec 30 - Fri, Jan 3
1:51 pm - 7:28 pmCLE-ORD
6h 37m1 stop
8:40 pm - 11:00 pmORD-CLE
1h 20mnonstop
$212American Airlines
Find Deal
Mon, Dec 16 - Tue, Dec 17
6:05 am - 1:20 pmCLE-MDW
8h 15m1 stop
$54Frontier
Find Deal
Wed, Dec 18
6:05 am - 1:49 pmCLE-ORD
8h 44m1 stop
$54Frontier
Find Deal
Wed, Dec 18
10:57 am - 11:35 amCLE-ORD
1h 38mnonstop
$79United Airlines
Find Deal
Tue, Dec 24
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
$79Southwest
Find Deal
Tue, Dec 24
7:00 am - 7:39 amCLE-ORD
1h 39mnonstop
$84United Airlines
Find Deal
Thu, Jan 9
6:05 am - 8:50 amCLE-MDW
3h 45m1 stop
$88Delta
Find Deal
Wed, Jan 1
7:30 pm - 10:20 pmCLE-MDW
3h 50m1 stop
$93Southwest
Find Deal
Tue, Dec 31
7:05 am - 1:08 pmCLE-MDW
7h 03m2 stops
$98Delta
Find Deal
Mon, Jan 6
6:27 am - 7:09 amCLE-ORD
1h 42mnonstop
$124American Airlines
Find Deal
Mon, Dec 30
8:14 pm - 11:37 pmCLE-ORD
4h 23m1 stop
$133American Airlines
Find Deal
Mon, Dec 30
7:12 pm - 11:59 pmCLE-ORD
5h 47m1 stop
8:01 pm - 8:38 amORD-CLE
11h 37m1 stop
$239Frontier
Find Deal
Tue, Nov 26 - Wed, Nov 27
2:22 pm - 11:59 pmCLE-ORD
10h 37m1 stop
8:01 pm - 8:38 amORD-CLE
11h 37m1 stop
$242Frontier
Find Deal
Sat, Nov 23 - Wed, Nov 27
6:47 am - 7:25 amCLE-ORD
1h 38mnonstop
8:25 pm - 10:48 pmORD-CLE
1h 23mnonstop
$304American Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:47 am - 7:25 amCLE-ORD
1h 38mnonstop
10:29 am - 5:17 pmORD-CLE
5h 48m1 stop
$314American Airlines
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:30 am - 6:50 amCLE-MDW
1h 20mnonstop
9:35 am - 11:50 amMDW-CLE
1h 15mnonstop
$335Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
12:55 pm - 1:10 pmCLE-MDW
1h 15mnonstop
6:20 am - 1:20 pmMDW-CLE
6h 00m1 stop
$344Southwest
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:01 am - 12:49 pmCLE-MDW
7h 48m2 stops
1:30 pm - 7:58 pmMDW-CLE
5h 28m1 stop
$358Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
6:01 am - 11:40 amCLE-ORD
6h 39m1 stop
1:35 pm - 12:25 amORD-CLE
9h 50m2 stops
$358Delta
Find Deal
Tue, Nov 26 - Tue, Dec 3
11:00 am - 11:31 amCLE-ORD
1h 31mnonstop
10:45 am - 1:07 pmORD-CLE
1h 22mnonstop
$485United Airlines
Find Deal
Tue, Nov 26 - Thu, Nov 28
6:00 am - 9:49 amCLE-ORD
4h 49m1 stop
7:30 am - 9:52 amORD-CLE
1h 22mnonstop
$495United Airlines
Find Deal
Tue, Nov 26 - Thu, Nov 28
6:00 am - 6:35 amCLE-ORD
1h 35mnonstop
12:53 pm - 3:17 pmORD-CLE
1h 24mnonstop
$157United Airlines
Find Deal
Tue, Dec 17 - Tue, Dec 17
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
7:25 pm - 9:40 pmMDW-CLE
1h 15mnonstop
$158Southwest
Find Deal
Tue, Dec 31 - Tue, Jan 7
11:00 am - 11:31 amCLE-ORD
1h 31mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$162United Airlines
Find Deal
Wed, Dec 11 - Sat, Dec 14
6:10 am - 6:35 amCLE-MDW
1h 25mnonstop
7:00 pm - 9:15 pmMDW-CLE
1h 15mnonstop
$163Southwest
Find Deal
Sat, Dec 14 - Tue, Dec 17
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$167United Airlines
Find Deal
Fri, Dec 13 - Mon, Dec 16
6:35 am - 6:55 amCLE-MDW
1h 20mnonstop
9:20 pm - 11:30 pmMDW-CLE
1h 10mnonstop
$168Southwest
Find Deal
Fri, Dec 13 - Fri, Dec 13
6:40 am - 7:19 amCLE-ORD
1h 39mnonstop
8:04 am - 10:33 amORD-CLE
1h 29mnonstop
$177American Airlines
Find Deal
Thu, Jan 16 - Sat, Jan 18
7:00 pm - 7:20 pmCLE-MDW
1h 20mnonstop
6:20 pm - 8:35 pmMDW-CLE
1h 15mnonstop
$178Southwest
Find Deal
Mon, Jan 13 - Thu, Jan 16
6:27 am - 7:09 amCLE-ORD
1h 42mnonstop
8:34 pm - 11:10 pmORD-CLE
1h 36mnonstop
$207American Airlines
Find Deal
Mon, Dec 30 - Fri, Jan 3
6:35 am - 7:17 amCLE-ORD
1h 42mnonstop
8:34 pm - 11:10 pmORD-CLE
1h 36mnonstop
$227American Airlines
Find Deal
Wed, Dec 11 - Sun, Jan 5

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets
American Airlines
Dec 30
CLE6:27 amCleveland Hopkins Intl
1h 42m
ORD7:09 amChicago O'Hare Intl
Jan 3
ORD8:34 pmChicago O'Hare Intl
1h 36m
CLE11:10 pmCleveland Hopkins Intl
American Airlines
Dec 16
CLE1:51 pmCleveland Hopkins Intl
6h 37m
1 stop
ORD7:28 pmChicago O'Hare Intl
Dec 17
ORD8:40 pmChicago O'Hare Intl
1h 20m
CLE11:00 pmCleveland Hopkins Intl
American Airlines
Jan 11
CLE1:52 pmCleveland Hopkins Intl
6h 34m
1 stop
ORD7:26 pmChicago O'Hare Intl
Jan 12
ORD6:00 pmChicago O'Hare Intl
1h 30m
CLE8:30 pmCleveland Hopkins Intl

Spirit Airlines flights from Cleveland to Chicago

Our best Spirit Airlines deals on Cleveland to Chicago flight tickets
Spirit Airlines
Dec 11
CLE5:00 amCleveland Hopkins Intl
12h 06m
1 stop
ORD4:06 pmChicago O'Hare Intl
Dec 14
ORD5:00 amChicago O'Hare Intl
17h 59m
1 stop
CLE11:59 pmCleveland Hopkins Intl
Spirit Airlines
Dec 9
CLE5:00 amCleveland Hopkins Intl
20h 33m
3 stops
ORD12:33 amChicago O'Hare Intl
Dec 11
ORD6:33 pmChicago O'Hare Intl
28h 26m
3 stops
CLE11:59 pmCleveland Hopkins Intl
Spirit Airlines
Dec 12
CLE5:00 amCleveland Hopkins Intl
17h 07m
1 stop
ORD9:07 pmChicago O'Hare Intl
Dec 15
ORD9:58 amChicago O'Hare Intl
13h 01m
1 stop
CLE11:59 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 $230.

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 $235. 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 $297.

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 $296.

What is the cheapest Cleveland Hopkins Intl to Chicago flight route?

Fly from Cleveland Hopkins Intl to Chicago O'Hare Intl 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 60 days out, which is when prices tend to be around $263. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $167.

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 November 2024, prices for Cleveland to Chicago flights are approximately 47% 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 $108.
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)

  • 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
3,536 reviews
Search Frontier flights
American AirlinesPriceFrom $107Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $138Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $156Free CancellationRating
8.0
8,755 reviews
Search Delta flights
SouthwestPriceFrom $168Free CancellationRating
8.1
5,005 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 $277 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 9,172 reviews) operates around 29 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $311, 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.


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.


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Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago