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 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Cleveland

Explore current cheapest deals departing from Chicago to Cleveland

Round trip

Sort by: Cheapest

July 8 - July 15

Cheapest

Best

MDW - Cleveland

$189

$109

Round trip

July 7 - July 14

Cheapest

Earliest

ORD - Cleveland

$163

$109

Round trip

July 7 - July 21

Cheapest

Earliest

ORD - Cleveland

$148

$109

Round trip

July 15 - July 29

Cheapest

ORD - Cleveland

$147

$109

Round trip

July 14 - July 22

Cheapest

ORD - Cleveland

$159

$109

Round trip

July 8 - July 21

Cheapest

ORD - Cleveland

$148

$109

Round trip

July 15 - July 21

Cheapest

ORD - Cleveland

$162

$109

Round trip

July 15 - July 28

Cheapest

ORD - Cleveland

$147

$109

Round trip

July 7 - July 15

Cheapest

Earliest

ORD - Cleveland

$160

$109

Round trip

July 8 - July 14

Cheapest

ORD - Cleveland

$163

$109

Round trip

Unlock all 500+ flight deals to Cleveland and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Cleveland

Fares for flights from Chicago to Cleveland are typically $181–$814, with a median of $253. Right now, current fares are significantly above the typical level, with only 13% of recent fares classified as a good price. New deals appear almost daily, suggesting frequent opportunities to find better pricing.

When looking for cheap flights from Chicago to Cleveland, the cheapest time to fly is often in December or January, with median fares of $174 for both months. June also presents a more affordable option, with a median fare of $207.

A typical journey from Chicago to Cleveland takes about 3h 9m, including connections. This route has a mixed offering of flights, meaning a meaningful share are non-stop, while the rest connect at least once. For itineraries that do include connections, the median number of stopovers is 4.

The distance between Chicago and Cleveland is 507 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick travel experience, often completed within a few hours.

How much is a round trip from Chicago to Cleveland

Regular price: $149 - $264

Prices are currently below the regular range.

The regular price range for flights from Chicago to Cleveland is $149-$264. The current lowest deal is $109 with Southwest Airlines for travel from Jul 8-Jul 15.

now $109

Low $149

High $264

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

United Airlines

Last-minute flights going from Chicago to Cleveland

Wed, Jun 17

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$655

$325

One-way

Thu, Jun 18

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$764

$344

One-way

Thu, Jun 18

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$656

$344

One-way

Fri, Jun 19

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$771

$344

One-way

Fri, Jun 19

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$758

$391

One-way

Fri, Jun 19

⌛ Last-Minute

MDW - Cleveland

Chicago (MDW) - Cleveland (CLE)

Frontier Airlines

$773

$411

One-way

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

1 night

Jun 20 - Jun 21

$773 → $336

57%

4 nights

Jun 20 - Jun 24

$758 → $326

57%

2 nights

Jun 19 - Jun 21

$771 → $344

55%

3 nights

Jun 18 - Jun 21

$764 → $344

55%

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, with deals around $109.

📅 Best time to fly

January, December, and June are cheapest

Historically, the cheapest months to fly are January, December, and June, with median prices around $174.

⏱️ Flight duration

Short-haul flights average 3h 9m

Flights from Chicago to Cleveland are short-haul, typically lasting 3 hours and 9 minutes.

✈️ Airlines & availability

Frequent deals, mixed direct flight availability

Deals for this route are frequent, with a mixed availability of direct and connecting flights.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines is one of the carriers providing direct flights from Chicago to Cleveland.

🎯 Booking tip

Good prices are available 13% of the time

Historically, good prices for flights from Chicago to Cleveland are available 13% of the time.

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

Chicago Rockford International (RFD)

Chicago Rockford International offers another departure option for your trip from Chicago to Cleveland.

📍 ~115 km from Chicago city center (reachable by car)

💸 Flights from ~$196

O Hare International (ORD)

O Hare International is a major airport providing flights from Chicago to Cleveland.

📍 ~25 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 Airport can be a useful alternative for easier navigation and shorter security lines.

📍 ~80 km from Cleveland (reachable by car)

💸 Flights from ~$188

Detroit Metropolitan (DTW)

Detroit Metropolitan Airport is a major international hub that often offers lower fares on long-haul routes.

📍 ~160 km from Cleveland (reachable by car)

💸 Flights from ~$177

Pittsburgh International (PIT)

Cheapest

Pittsburgh International Airport is a large airport with diverse carrier options and reliable infrastructure.

📍 ~150 km from Cleveland (reachable by car)

💸 Flights from ~$137

John Glenn Columbus International (CMH)

John Glenn Columbus International Airport is a major domestic airport with a strong presence of low-cost carriers.

📍 ~200 km from Cleveland (reachable by car)

💸 Flights from ~$157

Erie International (ERI)

Erie International Airport offers a small, low-stress terminal environment with limited flight schedules.

📍 ~150 km from Cleveland (reachable by car)

💸 Flights from ~$278

Business & First Class Flight Deals to Cleveland

Cleveland, United States

36% AI deal score

$881

From ORD

Elite

Nov 01

Cleveland, United States

35% AI deal score

$2,136

Frequently Asked Questions About Flights to Cleveland

Historically, booking your flight to Cleveland from Chicago 60+ days in advance typically yields the lowest prices, with an average of $322. Prices tend to increase as the departure date approaches. For instance, flights booked within 28-59 days of travel average around $658. Booking within 0-6 days of departure sees the average price rise to $1764, based on data from the trailing 90 days.

Across the trailing quarter, a good price for a flight from Chicago to Cleveland is considered to be $181 or less. The median price for this route was $253. Prices can go higher, with 75% of prices observed being $814 or less. These figures are based on historical data from the last 90 days.

Historically, December and January have been the cheapest months to fly from Chicago to Cleveland, both with a median price of $174. June also offers a relatively good median price of $207. The annual median price for this route is $253, based on data from the trailing 270 days.

Related routes

Consider alternative routes from Chicago

Flights from Chicago to Abu Dhabi Flights from Chicago to Accra Flights from Chicago to Addis Ababa Flights from Chicago to Adelaide Flights from Chicago to Ahmedabad Flights from Chicago to Albuquerque Flights from Chicago to Amman Flights from Chicago to Amsterdam Flights from Chicago to Athens Flights from Chicago to Atlanta Flights from Chicago to Austin Flights from Chicago to Baghdad