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Cheap flights from Cleveland to Chicago from $55

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 3/11. 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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0 bags

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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.
1:29 pm - 11:50 pmCLE-MDW
11h 21m1 stop
4:40 pm - 12:55 amMDW-CLE
7h 15m1 stop
$110Frontier
Find Deal
lun., abr. 7 - mar., abr. 8
9:17 pm - 8:05 amCLE-ORD
11h 48m1 stop
7:35 am - 9:05 pmORD-CLE
12h 30m1 stop
$120Frontier
Find Deal
jue., may. 8 - dom., may. 11
6:00 am - 3:10 pmCLE-ORD
10h 10m1 stop
6:25 pm - 12:13 pmORD-CLE
16h 48m2 stops
$138Spirit Airlines
Find Deal
mar., mar. 25 - mar., mar. 25
6:00 am - 3:10 pmCLE-ORD
10h 10m1 stop
7:21 pm - 12:13 pmORD-CLE
15h 52m1 stop
$155Spirit Airlines
Find Deal
mar., mar. 25 - mar., mar. 25
6:25 am - 7:00 amCLE-ORD
1h 35mnonstop
8:30 pm - 10:56 pmORD-CLE
1h 26mnonstop
$157American Airlines
Find Deal
lun., mar. 24 - lun., mar. 31
7:30 pm - 7:50 pmCLE-MDW
1h 20mnonstop
10:15 am - 12:25 pmMDW-CLE
1h 10mnonstop
$157Southwest
Find Deal
lun., mar. 17 - mar., mar. 18
6:25 am - 7:00 amCLE-ORD
1h 35mnonstop
8:30 pm - 10:56 pmORD-CLE
1h 26mnonstop
$158American Airlines
Find Deal
jue., mar. 13 - lun., mar. 17
6:00 am - 9:38 amCLE-ORD
4h 38m1 stop
9:19 pm - 11:44 pmORD-CLE
1h 25mnonstop
$167United Airlines
Find Deal
mar., mar. 25 - lun., mar. 31
1:20 pm - 1:40 pmCLE-MDW
1h 20mnonstop
3:35 pm - 10:50 pmMDW-CLE
6h 15m1 stop
$167Southwest
Find Deal
lun., mar. 17 - mar., mar. 18
7:00 am - 7:38 amCLE-ORD
1h 38mnonstop
7:30 am - 9:51 amORD-CLE
1h 21mnonstop
$187United Airlines
Find Deal
sáb., mar. 8 - vie., mar. 14

Spirit Airlines flights from Cleveland to Chicago

Our best Spirit Airlines deals on Cleveland to Chicago flight tickets
Spirit Airlines
Mar 25
CLE6:00 amCleveland Hopkins Intl
10h 10m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 25
ORD6:25 pmChicago O'Hare Intl
16h 48m
2 stops
CLE12:13 pmCleveland Hopkins Intl
Spirit Airlines
Mar 25
CLE6:00 amCleveland Hopkins Intl
10h 10m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 25
ORD7:21 pmChicago O'Hare Intl
15h 52m
1 stop
CLE12:13 pmCleveland Hopkins Intl
Spirit Airlines
Mar 25
CLE6:00 amCleveland Hopkins Intl
10h 10m
1 stop
ORD3:10 pmChicago O'Hare Intl
Mar 31
ORD8:33 pmChicago O'Hare Intl
14h 40m
2 stops
CLE12:13 pmCleveland Hopkins Intl

American Airlines flights from Cleveland to Chicago

Our best American Airlines deals on Cleveland to Chicago flight tickets
American Airlines
Mar 24
CLE6:25 amCleveland Hopkins Intl
1h 35m
ORD7:00 amChicago O'Hare Intl
Mar 31
ORD8:30 pmChicago O'Hare Intl
1h 26m
CLE10:56 pmCleveland Hopkins Intl
American Airlines
Mar 13
CLE6:25 amCleveland Hopkins Intl
1h 35m
ORD7:00 amChicago O'Hare Intl
Mar 17
ORD8:30 pmChicago O'Hare Intl
1h 26m
CLE10:56 pmCleveland Hopkins Intl
American Airlines
Mar 15
CLE7:14 pmCleveland Hopkins Intl
1h 31m
ORD7:45 pmChicago O'Hare Intl
Mar 17
ORD8:30 pmChicago O'Hare Intl
1h 26m
CLE10:56 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 April is, on average, the cheapest month to fly to Chicago from Cleveland, with most prices found around $229. If you’re not able to fly to Chicago in April, then September is your next best option. Flight prices from Cleveland to Chicago during September average around $237.

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 Friday when prices can be found for as low as $497. 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 $702.

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 $496. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $1,082.

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?

You are more likely to see cheaper flights to Chicago from Cleveland when booking 18 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $289 when searching 18 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 $185 on momondo.

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.

How have Cleveland to Chicago flight prices changed over time?

As of February 2025, prices for Cleveland to Chicago flights are approximately 77% 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

$55

Fastest flight time

1h 15m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun

Airports in Chicago

2 airports
The best one-way flight to Chicago from Cleveland in the past 72 hours is $55. The best round-trip flight deal from Cleveland to Chicago found on momondo in the last 72 hours is $110.
The fastest flight from Cleveland to Chicago takes 1h 15m
Direct flights go from Cleveland to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. Airlines offering direct flights are: United Airlines, Southwest and American Airlines.
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 $83. 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
6.0
3,352 reviews
Search Frontier flights
American AirlinesPriceFrom $114Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
8,754 reviews
Search United Airlines flights
DeltaPriceFrom $156Free CancellationRating
8.0
8,203 reviews
Search Delta flights
SouthwestPriceFrom $168Free CancellationRating
8.1
4,395 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 $281 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 8,754 reviews) operates around 38 flights from Cleveland to Chicago in any given week. The average United Airlines airfare for this route is around $317, with deals from around $143 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 locations
Merrillville
Hammond
New Buffalo
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Munster
Crown Point
Schererville
Monticello
Chesterton
Porter
Griffith
Saint John

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