Can I fly direct from Chicago to Cleveland?

Yes, direct flights from Chicago to Cleveland are available. Historically, approximately 38.7% of all flights on this route have been direct. For flights with one or more stops, the median number of stopovers was 2.

How long does it take to fly from Chicago to Cleveland?

A direct flight from Chicago to Cleveland typically takes 1 hour and 24 minutes, covering a distance of 507 kilometers. Flights with one stop have a significantly longer median duration, averaging 7 hours and 41 minutes. This difference highlights the convenience of direct routes for this journey.

Are there frequently good prices on flights from Chicago to Cleveland?

Yes, historically, good prices on flights from Chicago to Cleveland are frequent. This route is classified as one with consistently available deals. Travelers can often find competitive fares for this particular journey.

Flights From Chicago

To Cleveland

Cheap Flights from Chicago to Cleveland

Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.

Deals from

Chicago

RatePunk searches hundreds of travel sites at once for deals on flights to Cleveland

Prices updated 2 days ago

405 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Jul 26, 2026.)

Today’s best flight deals from Chicago to Cleveland

Explore current cheapest deals departing from Chicago to Cleveland

2026-08-05 – 2026-08-08
CHI - Cleveland
50% AI deal score
$161
$117
Round trip
2026-08-10 – 2026-08-11
CHI - Cleveland
50% AI deal score
$158
$117
Round trip
2026-08-17 – 2026-08-20
CHI - Cleveland
49% AI deal score
$142
$117
Round trip
2026-08-05 – 2026-08-10
CHI - Cleveland
48% AI deal score
$139
$117
Round trip
2026-08-19 – 2026-08-22
CHI - Cleveland
49% AI deal score
$153
$117
Round trip
2026-08-15 – 2026-08-17
CHI - Cleveland
49% AI deal score
$154
$117
Round trip
2026-08-12 – 2026-08-13
CHI - Cleveland
49% AI deal score
$145
$117
Round trip
2026-08-15 – 2026-08-22
CHI - Cleveland
48% AI deal score
$144
$117
Round trip
2026-08-10 – 2026-08-19
CHI - Cleveland
47% AI deal score
$136
$117
Round trip
2026-09-09 – 2026-09-21
CHI - Cleveland
44% AI deal score
$114
$117
Round trip

Chicago to Cleveland: Overview

Insights for flights from Chicago to Cleveland

Fares for flights from Chicago to Cleveland typically range from $240–$583, with a median of $392. Right now, current fares are significantly above the typical level for this route. Only 8% of recent fares were classified as a good price, indicating that finding cheap flights from Chicago to Cleveland can be challenging at present.

For travelers seeking the cheapest time to fly from Chicago to Cleveland, the data shows that December and January are typically the most affordable months, both with median fares of $174. June also presents a more budget-friendly option, with a median fare of $207.

A typical journey from Chicago to Cleveland takes about 3h 9m, including connections. Most itineraries for this route connect at least once, with the median number of stopovers for connecting flights being 2. This means that while some direct flights from Chicago to Cleveland are available, you should generally expect a journey that includes a layover.

The route from Chicago to Cleveland covers a distance of 507 kilometers, classifying it as a short-haul flight. This distance typically translates to a relatively quick travel experience, though the presence of connections can extend the overall journey time.

How much is a round trip from Chicago to Cleveland

Regular price: $114 - $234

Prices are currently below the regular range.

The regular price range for flights from Chicago to Cleveland is $114-$234. The current lowest deal is $96 with Southwest Airlines, for travel from Aug 27-Aug 29.

now $96

Low $114

High $234

The cheapest time to fly from Chicago to Cleveland

The cheapest month to fly from Chicago to Cleveland is January, with a median price of $174. The most expensive month is May, with a median price of $1904. Prices are generally lower from January to December.

January

Cheapest

Flights from $174

May

Most Expensive

Flights from $1,904

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Cleveland

Southwest Airlines

Last-minute flights going from Chicago to Cleveland

Thu, Aug 6

⌛ Last-Minute

RFD - Cleveland

Chicago (RFD) - Cleveland (CLE)

Allegiant Air

$366

$257

One-way

Thu, Aug 13

⌛ Last-Minute

RFD - Cleveland

Chicago (RFD) - Cleveland (CLE)

Allegiant Air, Frontier Airlines

$240

$182

One-way

Thu, Aug 13

⌛ Last-Minute

RFD - Cleveland

Chicago (RFD) - Cleveland (CLE)

Allegiant Air

$321

$232

One-way

Thu, Aug 13

⌛ Last-Minute

RFD - Cleveland

Chicago (RFD) - Cleveland (CLE)

Allegiant Air

$321

$235

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Southwest Airlines

$157

$97

One-way

Sat, Aug 15

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Southwest Airlines

$159

$117

One-way

Biggest price drops on these dates for flights from Chicago to Cleveland

7 nights

Nov 3 - Nov 10

$504 → $156

69%

2 nights

Nov 6 - Nov 8

$538 → $247

54%

2 nights

Nov 7 - Nov 9

$369 → $117

68%

6 nights

Nov 1 - Nov 7

$345 → $196

43%

Popular Airports to fly from Chicago to Cleveland

Chicago - Cleveland route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Chicago to Cleveland are below the typical level for this route.

📅 Best time to fly

Fly in December, January, or June for the best prices.

Historically, December, January, and June offer median prices around $174-$207, which is below the typical level.

⏱️ Flight duration

Flights typically take 3h 9m.

The median flight duration for this route is 3 hours and 9 minutes, classifying it as a short-haul flight.

✈️ Airlines & availability

Southwest Airlines offers direct flights.

Southwest Airlines provides direct flights on this route, with frequent deals available.

🏆 Airline highlight

Southwest Airlines has a direct deal for $96.

A direct flight from Chicago Midway to Cleveland Hopkins is available for $96 with Southwest Airlines.

🎯 Booking tip

Deals appear frequently on this route.

Deals for flights from Chicago to Cleveland are frequent, appearing often within a 30-day window.

Chicago main airports to depart from

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a good choice for flights from Chicago to Cleveland, often offering competitive prices.

📍 ~15 km from Chicago city center (reachable by car or train)

💸 Flights from ~$109

Cleveland main airports to arrive at

Cleveland Hopkins International (CLE)

Cheapest

Cleveland Hopkins International Airport is a convenient arrival choice for flights from Chicago to Cleveland.

📍 ~17 km from Cleveland city center (reachable by car or train)

💸 Flights from ~$109

Airports nearby Cleveland used as alternative

Akron–Canton (CAK)

Akron–Canton is a useful alternative for Cleveland travelers due to its proximity and ease of use.

📍 ~75 km from Cleveland (reachable by car)

💸 Flights from ~$174

Business & First Class Flight Deals to Cleveland

49% AI deal score

$803

$701

Save $102

Frequently Asked Questions About Flights to Cleveland

Historically, the lowest prices for flights from Chicago to Cleveland are found when booking 60 or more days in advance. Across the trailing quarter, flights booked within this window had an average price of $322. Prices tend to increase significantly closer to the departure date, with flights booked 28-59 days out averaging $658, and those booked 0-6 days before departure averaging $1764.

Based on data from the trailing 90 days, a good price for a flight from Chicago to Cleveland is considered to be $240 or less. The median price for this route was $392. Prices typically range, with 75% of observed prices falling below $583.

Historically, December and January have been the cheapest months to fly from Chicago to Cleveland, both with a median price of $174. June also offered competitive prices, with a median of $207. The annual median price for this route, observed over a 270-day window, was $392.

Related routes

More routes from Chicago

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Flights to Cleveland from other cities

Flights from Charleston to Cleveland Flights from Charlotte to Cleveland Flights from Dallas to Cleveland Flights from Denver to Cleveland Flights from Detroit to Cleveland Flights from Hong Kong to Cleveland Flights from Houston to Cleveland Flights from Las Vegas to Cleveland Flights from Los Angeles to Cleveland Flights from Miami to Cleveland Flights from Minneapolis to Cleveland Flights from Newcastle upon Tyne to Cleveland

Chicago to Cleveland: Overview

Insights for flights from Chicago to Cleveland

How much is a round trip from Chicago to Cleveland

Regular price: $114 - $234

Prices are currently below the regular range.

The regular price range for flights from Chicago to Cleveland is $114-$234. The current lowest deal is $96 with Southwest Airlines, for travel from Aug 27-Aug 29.

now $96

Low $114

High $234

The cheapest time to fly from Chicago to Cleveland

January

Cheapest

Flights from $174

May

Most Expensive

Flights from $1,904

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec