How many flights from Cleveland to Chicago are non-stop?

Across the trailing quarter, approximately 44.5% of flights from Cleveland to Chicago are non-stop. For flights that include stopovers, the median number of stopovers is 2. This indicates that while direct options are available, a significant portion of routes involve connections. Travelers should check flight details to see if a direct flight or a connecting flight best suits their needs.

How long is the flight from Cleveland to Chicago?

The typical direct flight from Cleveland to Chicago has a median duration of 1 hour and 36 minutes, covering a distance of 492 kilometers. Flights with one stop, however, are considerably longer, with a median duration of 10 hours and 18 minutes. Travelers should account for these differences when planning their journey, as connecting flights can significantly extend travel time.

How often do cheap flights from Cleveland to Chicago come up?

Historically, cheap flights from Cleveland to Chicago come up frequently. This route is classified as one where good deals appear often. Travelers interested in this route can typically find favorable prices with regularity. This consistent availability makes it easier to plan a trip between these two cities without extensive waiting for a deal.

Flights From Cleveland

To Chicago

Cheap Flights from Cleveland to Chicago

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Deals from

Cleveland

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

Prices updated 6 days ago

456 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 31, 2026.)

Today’s best flight deals from Cleveland to Chicago

Explore current cheapest deals departing from Cleveland to Chicago

2026-09-23 – 2026-09-26
CLE - Chicago
45% AI deal score
$120
$115
Round trip
2026-09-24 – 2026-09-28
CLE - Chicago
45% AI deal score
$120
$115
Round trip
2026-10-01 – 2026-10-03
CLE - Chicago
46% AI deal score
$123
$115
Round trip
2026-10-08 – 2026-10-15
CLE - Chicago
44% AI deal score
$120
$115
Round trip
2026-10-08 – 2026-10-10
CLE - Chicago
45% AI deal score
$126
$115
Round trip
2026-10-06 – 2026-10-12
CLE - Chicago
44% AI deal score
$116
$115
Round trip
2026-10-17 – 2026-10-24
CLE - Chicago
44% AI deal score
$116
$115
Round trip
2026-10-19 – 2026-10-26
CLE - Chicago
44% AI deal score
$116
$115
Round trip
2026-11-17 – 2026-11-18
CLE - Chicago
44% AI deal score
$114
$115
Round trip
2027-02-11 – 2027-02-13
CLE - Chicago
45% AI deal score
$119
$115
Round trip

Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

For flights from Cleveland to Chicago, fares typically range from $206–$575, with a median of $315. Right now, current fares are above the typical level, and only 3% of recent fares were classified as a good price.

If you are looking for cheap flights from Cleveland to Chicago, the cheapest months to fly are January, with a median fare of $139, followed by February at $172, and November at $174. New deals appear almost daily for this route.

A typical journey from Cleveland to Chicago takes about 1h 36m. This route is classified as short-haul, covering a distance of 492 km.

When flying from Cleveland to Chicago, 44.5% of recent fares were for direct flights from Cleveland to Chicago. For itineraries that include connections, the typical number of stopovers is 2.

How much is a round trip from Cleveland to Chicago

Regular price: $95 - $266

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

The regular price range for flights from Cleveland to Chicago is typically between $95 and $266. The current lowest deal is $117 on Kayak, for travel from Sep 17-Sep 21.

now $117

Low $95

High $266

The cheapest time to fly from Cleveland to Chicago

The cheapest month to fly from Cleveland to Chicago is January, with a median price of $139. The most expensive month is August, with a median price of $371. Prices are generally lower from January to December.

January

Cheapest

Flights from $139

August

Most Expensive

Flights from $371

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Cleveland to Chicago

United Airlines

Last-minute flights going from Cleveland to Chicago

Mon, Aug 31

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

$513

$524

One-way

Sat, Sep 5

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$329

$261

One-way

Sat, Sep 5

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$365

$278

One-way

Fri, Sep 11

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$288

$225

One-way

Thu, Sep 17

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

$126

$117

One-way

Fri, Sep 18

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

$124

$229

One-way

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

2 nights

Sep 17 - Sep 19

$264 → $117

56%

2 nights

Oct 1 - Oct 3

$255 → $117

54%

2 nights

Sep 24 - Sep 26

$248 → $117

53%

4 nights

Sep 24 - Sep 28

$248 → $117

53%

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Cleveland to Chicago are above the typical level at $117.

📅 Best time to fly

January offers the lowest median prices.

Historically, January has the lowest median prices at $139 for flights from Cleveland to Chicago.

⏱️ Flight duration

Direct flights take 1h 36m.

Direct flights from Cleveland to Chicago typically take 1h 36m, while connecting flights average 16h 48m.

✈️ Airlines & availability

44.5% of recent flights are direct.

Approximately 44.5% of recent flights from Cleveland to Chicago are direct, with frequent deals available.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one carrier that offers direct flights on the Cleveland to Chicago route.

🎯 Booking tip

Good prices are uncommon for this route.

Historically, good prices for flights from Cleveland to Chicago are uncommon, appearing only 3% of the time.

Cleveland main airports to depart from

Cleveland Hopkins International (CLE)

Cheapest

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

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

💸 Flights from ~$113

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights to Chicago from Cleveland.

📍 ~14 km from Chicago city center (reachable by car).

💸 Flights from ~$116

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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 ~$217

Business & First Class Flight Deals to Chicago

66% AI deal score

$3,884

$2,175

Save $1,709

Air Canada, +1

Business Class

From CLE

Elite

Sep 15

Chicago, United States

65% AI deal score

$3,933

$2,429

Save $1,504

Air Canada, +1

Business Class

From CLE

Elite

Sep 08

Chicago, United States

50% AI deal score

$3,136

$2,184

Save $952

Air Canada, +1

Business Class

From CLE

Elite

Sep 08

Chicago, United States

50% AI deal score

$3,220

$2,217

Save $1,003

Air Canada, +1

Business Class

From CLE

Elite

Sep 23

Chicago, United States

50% AI deal score

$3,696

$2,392

Save $1,304

Air Canada, +1

Business Class

From CLE

Elite

Sep 15

Chicago, United States

50% AI deal score

$3,800

$2,440

Save $1,360

Air Canada, +1

Business Class

From CLE

Elite

Oct 13

Chicago, United States

49% AI deal score

$2,620

$2,113

Save $507

Alaska Airlines, Inc.

Business Class

From CLE

Elite

Oct 09

Chicago, United States

49% AI deal score

$3,425

$2,382

Save $1,043

Air Canada, +1

Business Class

From CLE

Elite

Oct 09

Chicago, United States

49% AI deal score

$3,439

$2,449

Save $990

Air Canada, +1

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the best prices for flights from Cleveland to Chicago are found when booking 28-59 days in advance. During this period, the average price is typically around $194. Booking within 0-6 days of departure sees a significant increase, with average prices rising to approximately $726. Planning ahead by at least a month can lead to considerable savings on this route.

Based on historical data from the trailing 90 days, a good price for a flight from Cleveland to Chicago is considered to be $206 or less. The median price for this route has been $315. Prices can go higher, with 75% of fares being $575 or more. Travelers aiming for a budget-friendly trip should target fares around the $206 mark.

Historically, the cheapest months to fly from Cleveland to Chicago are January, with a median price of $139, and February, with a median price of $172. November also offers competitive pricing, with a median of $174. These months are typically more affordable compared to the annual median price of $315 for this route. Travelers looking for the lowest fares should consider these periods.

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Flights to Chicago from other cities

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Cleveland to Chicago: Overview

Insights for flights from Cleveland to Chicago

A typical journey from Cleveland to Chicago takes about 1h 36m. This route is classified as short-haul, covering a distance of 492 km.

When flying from Cleveland to Chicago, 44.5% of recent fares were for direct flights from Cleveland to Chicago. For itineraries that include connections, the typical number of stopovers is 2.

How much is a round trip from Cleveland to Chicago

Regular price: $95 - $266

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

The regular price range for flights from Cleveland to Chicago is typically between $95 and $266. The current lowest deal is $117 on Kayak, for travel from Sep 17-Sep 21.

now $117

Low $95

High $266

The cheapest time to fly from Cleveland to Chicago

January

Cheapest

Flights from $139

August

Most Expensive

Flights from $371

Jan

Feb

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Cleveland to Chicago

United Airlines

Last-minute flights going from Cleveland to Chicago

Mon, Aug 31

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

$513

$524

One-way

Sat, Sep 5

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$329

$261

One-way

Sat, Sep 5

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$365

$278

One-way

Fri, Sep 11

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

Frontier Airlines

$288

$225

One-way

Thu, Sep 17

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (MDW)

$126

$117

One-way

Fri, Sep 18

⌛ Last-Minute

CLE - Chicago

Cleveland (CLE) - Chicago (ORD)

$124

$229

One-way

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

2 nights

Sep 17 - Sep 19

$264 → $117

56%

2 nights

Oct 1 - Oct 3

$255 → $117

54%

2 nights

Sep 24 - Sep 26

$248 → $117

53%

4 nights

Sep 24 - Sep 28

$248 → $117

53%

Popular Airports to fly from Cleveland to Chicago

Cleveland - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Cleveland to Chicago are above the typical level at $117.

📅 Best time to fly

January offers the lowest median prices.

Historically, January has the lowest median prices at $139 for flights from Cleveland to Chicago.

⏱️ Flight duration

Direct flights take 1h 36m.

Direct flights from Cleveland to Chicago typically take 1h 36m, while connecting flights average 16h 48m.

✈️ Airlines & availability

44.5% of recent flights are direct.

Approximately 44.5% of recent flights from Cleveland to Chicago are direct, with frequent deals available.

🏆 Airline highlight

United Airlines offers direct flights.

United Airlines is one carrier that offers direct flights on the Cleveland to Chicago route.

🎯 Booking tip

Good prices are uncommon for this route.

Historically, good prices for flights from Cleveland to Chicago are uncommon, appearing only 3% of the time.

Cleveland main airports to depart from

Cleveland Hopkins International (CLE)

Cheapest

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

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

💸 Flights from ~$113

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights to Chicago from Cleveland.

📍 ~14 km from Chicago city center (reachable by car).

💸 Flights from ~$116

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

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 ~$217

Chicago, United States

49% AI deal score

$3,439

$2,449

Save $990

Air Canada, +1

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.

January offers the lowest median prices.

Direct flights take 1h 36m.

44.5% of recent flights are direct.

United Airlines offers direct flights.

Good prices are uncommon for this route.

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

Nov 04

Sep 10

Sep 11

Sep 15

Sep 15

Sep 08

Sep 08

Sep 23

Sep 15

Oct 13

Oct 09

Oct 09

Frequently Asked Questions About Flights to Chicago

How far in advance should I book a flight from Cleveland to Chicago?

What's a cheap fare from Cleveland to Chicago?

Which months have the cheapest flights from Cleveland to Chicago?

How many flights from Cleveland to Chicago are non-stop?

How long is the flight from Cleveland to Chicago?

How often do cheap flights from Cleveland to Chicago come up?

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.

January offers the lowest median prices.

Direct flights take 1h 36m.

44.5% of recent flights are direct.

United Airlines offers direct flights.

Good prices are uncommon for this route.

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

Nov 04

Sep 10

Sep 11

Sep 15

Sep 15

Sep 08

Sep 08

Sep 23

Sep 15

Oct 13

Oct 09

Oct 09

Frequently Asked Questions About Flights to Chicago

How far in advance should I book a flight from Cleveland to Chicago?

What's a cheap fare from Cleveland to Chicago?

Which months have the cheapest flights from Cleveland to Chicago?