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Cheap flights from Cleveland to Chicago from $53

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 1/30. 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.
11:25 am - 10:15 pmCLE-MDW
11h 50m1 stop
7:00 am - 4:11 pmMDW-CLE
8h 11m1 stop
$108Frontier
Find Deal
Mon, Nov 4 - Thu, Nov 7
7:10 pm - 12:34 amCLE-ORD
6h 24m1 stop
6:30 am - 2:19 pmORD-CLE
6h 49m1 stop
$108Frontier
Find Deal
Mon, Nov 4 - Thu, Nov 7
6:20 am - 2:00 pmCLE-ORD
8h 40m1 stop
3:10 pm - 10:10 pmORD-CLE
6h 00m1 stop
$186Southwest
Find Deal
Tue, Dec 10 - Wed, Dec 11
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
7:30 am - 9:52 amORD-CLE
1h 22mnonstop
$195United Airlines
Find Deal
Wed, Nov 13 - Thu, Nov 14
6:35 am - 7:17 amCLE-ORD
1h 42mnonstop
7:34 am - 10:01 amORD-CLE
1h 27mnonstop
$196American Airlines
Find Deal
Thu, Dec 5 - Thu, Dec 12
6:35 am - 6:55 amCLE-MDW
1h 20mnonstop
9:35 am - 11:50 amMDW-CLE
1h 15mnonstop
$196Southwest
Find Deal
Mon, Nov 18 - Tue, Nov 19
6:00 am - 9:49 amCLE-ORD
4h 49m1 stop
7:30 am - 9:52 amORD-CLE
1h 22mnonstop
$205United Airlines
Find Deal
Wed, Nov 13 - Sat, Nov 16
6:35 am - 7:17 amCLE-ORD
1h 42mnonstop
3:00 pm - 5:28 pmORD-CLE
1h 28mnonstop
$216American Airlines
Find Deal
Tue, Dec 17 - Sat, Jan 11
6:00 am - 9:50 amCLE-MDW
4h 50m1 stop
6:00 am - 1:12 pmMDW-CLE
6h 12m1 stop
$234Delta
Find Deal
Tue, Dec 10 - Wed, Dec 11
7:03 am - 12:21 pmCLE-ORD
6h 18m1 stop
7:35 pm - 11:58 pmORD-CLE
3h 23m1 stop
$234Delta
Find Deal
Tue, Nov 19 - Sun, Nov 24
1:09 pm - 8:53 pmCLE-MDW
8h 44m1 stop
$53Frontier
Find Deal
Thu, Jan 30
6:50 pm - 11:21 pmCLE-MDW
5h 31m1 stop
$54Frontier
Find Deal
Mon, Dec 9
6:47 am - 7:25 amCLE-ORD
1h 38mnonstop
$79American Airlines
Find Deal
Wed, Dec 4
6:15 pm - 6:30 pmCLE-MDW
1h 15mnonstop
$84Southwest
Find Deal
Wed, Dec 4
7:20 am - 12:15 pmCLE-MDW
5h 55m1 stop
$93Southwest
Find Deal
Tue, Dec 10
6:47 am - 7:25 amCLE-ORD
1h 38mnonstop
$94American Airlines
Find Deal
Thu, Nov 21
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
$98United Airlines
Find Deal
Fri, Nov 22
6:35 am - 8:50 amCLE-MDW
3h 15m1 stop
$117Delta
Find Deal
Tue, Nov 19
7:14 pm - 11:59 pmCLE-ORD
5h 45m1 stop
$117Delta
Find Deal
Tue, Nov 19
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
$128United Airlines
Find Deal
Tue, Nov 19
9:59 am - 5:59 pmCLE-MDW
9h 00m1 stop
9:15 am - 6:15 pmMDW-CLE
8h 00m1 stop
$208Frontier
Find Deal
Thu, Oct 24 - Mon, Nov 4
3:10 pm - 12:10 amCLE-ORD
10h 00m1 stop
11:26 am - 7:38 pmORD-CLE
7h 12m1 stop
$208Frontier
Find Deal
Thu, Oct 24 - Mon, Nov 4
7:00 am - 7:20 amCLE-MDW
1h 20mnonstop
9:50 pm - 12:10 amMDW-CLE
1h 20mnonstop
$490Southwest
Find Deal
Sun, Oct 27 - Sun, Oct 27
6:45 pm - 7:05 pmCLE-MDW
1h 20mnonstop
9:35 am - 11:50 amMDW-CLE
1h 15mnonstop
$491Southwest
Find Deal
Thu, Oct 24 - Mon, Nov 4
7:00 am - 7:29 amCLE-ORD
1h 29mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$510United Airlines
Find Deal
Sat, Oct 26 - Tue, Oct 29
10:30 am - 2:02 pmCLE-ORD
4h 32m1 stop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$520United Airlines
Find Deal
Sat, Oct 26 - Mon, Oct 28
7:24 am - 7:58 amCLE-ORD
1h 34mnonstop
9:45 am - 6:19 pmORD-CLE
7h 34m1 stop
$530American Airlines
Find Deal
Thu, Oct 24 - Mon, Nov 4
7:10 am - 5:03 pmCLE-MDW
10h 53m2 stops
1:12 pm - 12:39 amMDW-CLE
10h 27m2 stops
$546Delta
Find Deal
Thu, Oct 24 - Mon, Nov 4
2:21 pm - 7:28 pmCLE-ORD
6h 07m1 stop
6:00 am - 1:23 pmORD-CLE
6h 23m2 stops
$555Delta
Find Deal
Tue, Oct 22 - Sat, Oct 26
6:32 am - 7:05 amCLE-ORD
1h 33mnonstop
7:09 pm - 9:46 pmORD-CLE
1h 37mnonstop
$571American Airlines
Find Deal
Thu, Oct 24 - Sun, Oct 27
6:35 am - 7:17 amCLE-ORD
1h 42mnonstop
8:40 pm - 11:00 pmORD-CLE
1h 20mnonstop
$157American Airlines
Find Deal
Tue, Dec 10 - Wed, Dec 11
12:05 pm - 12:20 pmCLE-MDW
1h 15mnonstop
9:35 am - 11:50 amMDW-CLE
1h 15mnonstop
$168Southwest
Find Deal
Tue, Dec 10 - Wed, Dec 11
7:15 pm - 7:50 pmCLE-ORD
1h 35mnonstop
8:30 pm - 10:53 pmORD-CLE
1h 23mnonstop
$187American Airlines
Find Deal
Mon, Nov 18 - Mon, Nov 25
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
7:30 am - 9:52 amORD-CLE
1h 22mnonstop
$195United Airlines
Find Deal
Wed, Nov 13 - Thu, Nov 14
6:35 am - 6:55 amCLE-MDW
1h 20mnonstop
9:20 pm - 11:30 pmMDW-CLE
1h 10mnonstop
$196Southwest
Find Deal
Sun, Nov 17 - Mon, Nov 18
6:35 am - 7:17 amCLE-ORD
1h 42mnonstop
7:34 am - 10:01 amORD-CLE
1h 27mnonstop
$196American Airlines
Find Deal
Thu, Dec 5 - Thu, Dec 12
9:30 am - 10:03 amCLE-ORD
1h 33mnonstop
8:25 pm - 10:48 pmORD-CLE
1h 23mnonstop
$197American Airlines
Find Deal
Fri, Nov 29 - Tue, Dec 3
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
2:25 pm - 4:46 pmORD-CLE
1h 21mnonstop
$246United Airlines
Find Deal
Wed, Nov 20 - Wed, Nov 27
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$255United Airlines
Find Deal
Sat, Nov 16 - Fri, Nov 22
7:00 am - 7:31 amCLE-ORD
1h 31mnonstop
9:40 pm - 11:59 pmORD-CLE
1h 19mnonstop
$256United Airlines
Find Deal
Thu, Nov 14 - Sun, Nov 17

Spirit Airlines flights from Cleveland to Chicago

Our best Spirit Airlines deals on Cleveland to Chicago flight tickets
Spirit Airlines
Nov 1
CLE10:07 pmCleveland Hopkins Intl
27h 23m
1 stop
ORD12:30 amChicago O'Hare Intl
Nov 3
ORD5:25 amChicago O'Hare Intl
30h 00m
2 stops
CLE12:25 pmCleveland Hopkins Intl
Spirit Airlines
Nov 18
CLE5:12 amCleveland Hopkins Intl
32h 23m
2 stops
ORD12:35 pmChicago O'Hare Intl
Nov 25
ORD8:57 amChicago O'Hare Intl
13h 05m
2 stops
CLE11:02 pmCleveland Hopkins Intl
Spirit Airlines
Nov 18
CLE5:12 amCleveland Hopkins Intl
33h 32m
3 stops
ORD1:44 pmChicago O'Hare Intl
Nov 25
ORD8:57 amChicago O'Hare Intl
13h 05m
2 stops
CLE11:02 pmCleveland Hopkins Intl

Frontier flights from Cleveland to Chicago

Our best Frontier deals on Cleveland to Chicago flight tickets
Frontier
Nov 4
CLE7:10 pmCleveland Hopkins Intl
6h 24m
1 stop
ORD12:34 amChicago O'Hare Intl
Nov 7
ORD6:30 amChicago O'Hare Intl
6h 49m
1 stop
CLE2:19 pmCleveland Hopkins Intl
Frontier
Nov 2
CLE9:15 pmCleveland Hopkins Intl
22h 04m
1 stop
ORD6:19 pmChicago O'Hare Intl
Nov 6
ORD1:11 pmChicago O'Hare Intl
17h 28m
1 stop
CLE7:39 amCleveland Hopkins Intl
Frontier
Nov 3
CLE5:31 pmCleveland Hopkins Intl
8h 48m
1 stop
ORD1:19 amChicago O'Hare Intl
Nov 9
ORD6:48 pmChicago O'Hare Intl
12h 11m
1 stop
CLE7:59 amCleveland Hopkins Intl

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 cheapest month to fly from Cleveland to Chicago?

February. The cheapest time of year to fly to Chicago from Cleveland is February. Most expensive is October

What is the cheapest day to depart Cleveland for Chicago?

Saturday. The cheapest day of the week is typically Saturday. The most expensive is typically Monday

When is the cheapest time to fly from Cleveland to Chicago?

In the morning. Cleveland to Chicago flights are approximately 13% more expensive at noon than in the morning

What is the cheapest airline that flies to Chicago from Cleveland?

Frontier. Frontier, Southwest, and American Airlines are the most popular carriers operating from Cleveland to Chicago

What is the cheapest Cleveland to Chicago flight route?

Cleveland Hopkins Intl - Chicago Midway. Fly from Cleveland Hopkins Intl to Chicago Midway for the best Cleveland - Chicago flight prices

How far in advance should you book Cleveland to Chicago flights?

49 days before. The cheapest time to buy a flight from Cleveland to Chicago is approximately 49 days to departure

How many flights depart from Cleveland to Chicago on average per day?

The number of flights available between Cleveland and Chicago is 45 per day as of October 2024. The most frequent departure time is 7:00AM, with 47% of daily flights leaving at noon.

How many flights depart from Cleveland to Chicago on average per week?

The number of flights available between Cleveland and Chicago is 320 per week as of October 2024. The most frequent departure day is Monday, with 17% of weekly flights leaving on this day.

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?

You could potentially save up to 44% 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 October 2024, prices for Cleveland to Chicago flights are approximately 14% 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

$53

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 $53. 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)

  • 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 6h 05m 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 $99. 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 $99Free CancellationRating
6.1
3,618 reviews
Search Frontier flights
American AirlinesPriceFrom $108Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $144Free CancellationRating
7.4
9,285 reviews
Search United Airlines flights
DeltaPriceFrom $156Free CancellationRating
8.0
8,892 reviews
Search Delta flights
SouthwestPriceFrom $168Free CancellationRating
8.1
5,158 reviews
Search Southwest flights
  • Southwest Flights From Cleveland to Chicago

    Southwest flight deals from Cleveland to Chicago start from $168 round-trip. Over the 20 Southwest flights for this route in a normal week, average airfare is usually $253 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 9,285 reviews) operates around 29 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $295, with deals from around $144 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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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