Are direct flights from Cleveland to Chicago always the best option?

Direct flights offer convenience and save time, but they are not always the most budget-friendly choice. Flights with one or more layovers can often be cheaper, especially if you are flexible with your schedule. Consider your priorities for time versus cost when making your decision.

Can flexible travel dates help on Cleveland to Chicago flights?

Yes, being flexible with your travel dates can significantly impact the price of your flight. Shifting your departure or return by a few days, especially to travel during off-peak times, may lead to lower fares. Mid-week flights are often less expensive than weekend travel.

What extra costs should I check before booking Cleveland to Chicago flights?

Before booking, always check for potential extra costs such as baggage fees, seat selection charges, and in-flight services. Some airlines may also charge for printing boarding passes at the airport. These additional fees can add up and impact the total cost of your trip.

Flights From Cleveland

To Chicago

Cheap Flights from Cleveland to Chicago

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

Deals from

Cleveland

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

Prices updated 3 days ago

481 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Oct 19, 2026.)

Today’s best flight deals from Cleveland to Chicago

Explore current cheapest deals departing from Cleveland to Chicago

2026-12-02 – 2026-12-12
CLE - Chicago
70% AI deal score
$191
$135
Round trip
2026-12-01 – 2026-12-12
CLE - Chicago
69% AI deal score
$189
$135
Round trip
2026-12-02 – 2026-12-05
CLE - Chicago
73% AI deal score
$225
$135
Round trip
2026-12-08 – 2026-12-12
CLE - Chicago
73% AI deal score
$225
$135
Round trip
2026-12-01 – 2026-12-05
CLE - Chicago
73% AI deal score
$225
$135
Round trip
2026-11-16 – 2026-11-19
CLE - Chicago
41% AI deal score
$115
$143
Round trip
2026-11-12 – 2026-11-15
CLE - Chicago
41% AI deal score
$115
$143
Round trip
2026-11-09 – 2026-11-14
CLE - Chicago
41% AI deal score
$113
$143
Round trip
2026-11-09 – 2026-11-11
CLE - Chicago
41% AI deal score
$117
$143
Round trip
2026-11-09 – 2026-11-12
CLE - Chicago
41% AI deal score
$117
$143
Round trip

Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

A typical journey from Cleveland to Chicago covers a distance of 492 kilometers, making it a short-haul flight. This route is well-traveled, with new deals showing up several times a week, indicating a regular cadence of available fares.

For travelers seeking cheap flights from Cleveland to Chicago, the prices typically range from $277–$620, with a median of $441. Right now, current fares are significantly above the typical level, suggesting that prices are elevated compared to the historical median for this route.

When considering the cheapest time to fly from Cleveland to Chicago, September stands out as the most affordable month, with a median fare of just $134. Following closely are January, with a median of $185, and February, with a median of $187, offering other budget-friendly options for your trip.

The typical journey time for flights from Cleveland to Chicago is 1h 28m. However, it's important to note that most itineraries on this route connect at least once. For connecting flights, the median journey time can extend significantly, with a typical connecting journey taking 38h 17m. Only 30.9% of recent fares are for direct flights from Cleveland to Chicago, and when itineraries do connect, they typically involve 2 stopovers.

How much is a round trip from Cleveland to Chicago

Regular price: $150 - $277

Prices for flights from Cleveland to Chicago are currently within the regular range.

The regular price range for flights from Cleveland to Chicago is between $150 and $277. The current lowest deal is $168 with Frontier Airlines, for travel from Dec 12-Jan 6.

now $168

Low $150

High $277

The cheapest time to fly from Cleveland to Chicago

The cheapest month to fly from Cleveland to Chicago is September, with a median price of $134. The most expensive month is May, with a median price of $558. Generally, prices are lower from January to December.

September

Cheapest

Flights from $134

May

Most Expensive

Flights from $558

Jan

Feb

Mar

May

Aug

Sep

Oct

Nov

Dec

Direct flights from Cleveland to Chicago

United Airlines

Last-minute flights going from Cleveland to Chicago

Mon, Oct 19

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$386

$396

One-way

Thu, Oct 22

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$429

$415

One-way

Tue, Nov 3

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$221

$255

One-way

Wed, Nov 4

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$246

$294

One-way

Tue, Nov 10

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$223

$201

One-way

Sat, Nov 14

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$204

$216

One-way

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

1 night

Dec 1 - Dec 2

$227 → $169

26%

4 nights

Dec 1 - Dec 5

$225 → $169

25%

1 night

Dec 8 - Dec 9

$227 → $171

25%

3 nights

Dec 2 - Dec 5

$225 → $171

24%

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from CLE to CHI are above the typical level for the last 90 days.

📅 Best time to fly

Fly in September for the best prices

Historically, September is the cheapest month to fly, with a median price of $134.

⏱️ Flight duration

Direct flights average 1h 28m

The typical direct flight from Cleveland to Chicago takes 1 hour and 28 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Only 30.9% of recent flights from CLE to CHI are direct, with connecting flights dominant.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on this route recently.

🎯 Booking tip

Deals appear regularly

Deals for flights on this route appear regularly, typically within a 30-day window.

Cleveland main airports to depart from

Cleveland Hopkins International (CLE)

Cheapest

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

📍 ~16 km from Cleveland (reachable by car or train)

💸 Flights from ~$117

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your arrival in Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$99

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$163

Business & First Class Flight Deals to Chicago

Discover luxury on the budget with premium cabin class on flights from Cleveland to Chicago.

Elite

Best Elite deals to Chicago

Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.

From CLE

Elite

Dec 07

Chicago, United States

43% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Dec 07

Chicago, United States

43% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Dec 12

Chicago, United States

43% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Dec 30

Chicago, United States

43% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Nov 13

Chicago, United States

43% AI deal score

$478

United Airlines

Business Class

From CLE

Elite

Nov 09

Chicago, United States

43% AI deal score

$478

United Airlines

Business Class

From CLE

Elite

Dec 21

Chicago, United States

43% AI deal score

$478

United Airlines

Business Class

From CLE

Elite

Nov 25

Chicago, United States

42% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Nov 20

Chicago, United States

42% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Nov 19

Chicago, United States

42% AI deal score

$471

United Airlines

Business Class

From CLE

Elite

Jan 22

Chicago, United States

41% AI deal score

$478

United Airlines

Business Class

From CLE

Elite

Jan 07

Chicago, United States

41% AI deal score

$478

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

To find more affordable flights, consider being flexible with your travel dates and times. Comparing prices across different airlines and booking platforms can often reveal better deals. Looking into flights with layovers may also present lower-cost options.

Booking flights in advance, typically several weeks to a few months before your desired departure, can often result in better prices. Prices may fluctuate, so monitoring fares over time can help you identify a good booking window. Weekday travel can sometimes be more economical than weekend travel.

Comparing nearby airports at both your origin and destination can sometimes uncover more affordable flight options. While it may add to your ground travel time, the potential savings on airfare can be significant. Always factor in the cost and convenience of transportation to and from alternative airports.

Related routes

More routes from Cleveland

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Flights to Chicago from other cities

Flights from Cancún to Chicago Flights from Cape Town to Chicago Flights from Charlotte to Chicago Flights from Cincinnati to Chicago Flights from Colombo to Chicago Flights from Colorado Springs to Chicago Flights from Columbus to Chicago Flights from Dallas to Chicago Flights from Denver to Chicago Flights from Des Moines to Chicago Flights from Detroit to Chicago Flights from New Delhi to Chicago

Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

How much is a round trip from Cleveland to Chicago

Regular price: $150 - $277

Prices for flights from Cleveland to Chicago are currently within the regular range.

The regular price range for flights from Cleveland to Chicago is between $150 and $277. The current lowest deal is $168 with Frontier Airlines, for travel from Dec 12-Jan 6.

now $168

Low $150

High $277

The cheapest time to fly from Cleveland to Chicago

September

Cheapest

Flights from $134

May

Most Expensive

Flights from $558

Jan

Feb

Mar

May

Aug

Sep

Oct

Nov

Dec

Direct flights from Cleveland to Chicago

United Airlines

Last-minute flights going from Cleveland to Chicago

Mon, Oct 19

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$386

$396

One-way

Thu, Oct 22

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$429

$415

One-way

Tue, Nov 3

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$221

$255

One-way

Wed, Nov 4

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$246

$294

One-way

Tue, Nov 10

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$223

$201

One-way

Sat, Nov 14

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

Frontier Airlines

$204

$216

One-way

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

1 night

Dec 1 - Dec 2

$227 → $169

26%

4 nights

Dec 1 - Dec 5

$225 → $169

25%

1 night

Dec 8 - Dec 9

$227 → $171

25%

3 nights

Dec 2 - Dec 5

$225 → $171

24%

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares from CLE to CHI are above the typical level for the last 90 days.

📅 Best time to fly

Fly in September for the best prices

Historically, September is the cheapest month to fly, with a median price of $134.

⏱️ Flight duration

Direct flights average 1h 28m

The typical direct flight from Cleveland to Chicago takes 1 hour and 28 minutes.

✈️ Airlines & availability

Connecting flights are dominant

Only 30.9% of recent flights from CLE to CHI are direct, with connecting flights dominant.

🏆 Airline highlight

United Airlines offers direct flights

United Airlines has offered direct flights on this route recently.

🎯 Booking tip

Deals appear regularly

Deals for flights on this route appear regularly, typically within a 30-day window.

Cleveland main airports to depart from

Cleveland Hopkins International (CLE)

Cheapest

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

📍 ~16 km from Cleveland (reachable by car or train)

💸 Flights from ~$117

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub, offering extensive connections for your arrival in Chicago.

📍 ~25 km from Chicago city center (reachable by car)

💸 Flights from ~$99

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

Cheapest

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$163

Chicago, United States

41% AI deal score

$478

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Cleveland to Chicago

Today’s best flight deals from Cleveland to Chicago

Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

How much is a round trip from Cleveland to Chicago

The cheapest time to fly from Cleveland to Chicago

Direct flights from Cleveland to Chicago

Last-minute flights going from Cleveland to Chicago

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

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

Recent fares are above the typical level

Fly in September for the best prices

Direct flights average 1h 28m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

Cleveland main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 07

Dec 07

Dec 12

Dec 30

Nov 13

Nov 09

Dec 21

Nov 25

Nov 20

Nov 19

Jan 22

Jan 07

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Cleveland to Chicago?

When should I book flights from Cleveland to Chicago?

Should I compare nearby airports for flights from Cleveland to Chicago?

Are direct flights from Cleveland to Chicago always the best option?

Can flexible travel dates help on Cleveland to Chicago flights?

What extra costs should I check before booking Cleveland to Chicago flights?

Related routes

More routes from Cleveland

Flights to Chicago from other cities

Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

How much is a round trip from Cleveland to Chicago

The cheapest time to fly from Cleveland to Chicago

Direct flights from Cleveland to Chicago

Last-minute flights going from Cleveland to Chicago

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

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

Recent fares are above the typical level

Fly in September for the best prices

Direct flights average 1h 28m

Connecting flights are dominant

United Airlines offers direct flights

Deals appear regularly

Cleveland main airports to depart from

Chicago main airports to arrive at

Airports nearby Chicago used as alternative

Business & First Class Flight Deals to Chicago

Best Elite deals to Chicago

Dec 07

Dec 07

Dec 12

Dec 30

Nov 13

Nov 09

Dec 21

Nov 25

Nov 20

Nov 19

Jan 22

Jan 07

Frequently Asked Questions About Flights to Chicago

How can I find cheap flights from Cleveland to Chicago?

When should I book flights from Cleveland to Chicago?

Should I compare nearby airports for flights from Cleveland to Chicago?