Can I fly direct from Cincinnati to Chicago?

Yes, direct flights are available from Cincinnati to Chicago. Historically, approximately 36.6% of flights on this route have been direct. For journeys that involve connections, the median number of stopovers observed is 2. Travelers can choose between direct options or flights with one or more stops, depending on their preferences and availability.

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

A direct flight from Cincinnati to Chicago typically takes 1 hour and 37 minutes, covering a distance of 401 kilometers. For flights with one stop, the median duration is considerably longer, averaging 9 hours and 21 minutes. Travelers should consider these differences in flight time when planning their journey between the two cities.

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

Historically, cheap flights from Cincinnati to Chicago come up frequently. This route is classified as having frequent availability for deals. Travelers can typically find good opportunities for economical travel on this route across the trailing 30 days, indicating a consistent presence of favorable pricing.

Flights From Cincinnati

To Chicago

Cheap Flights from Cincinnati to Chicago

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

Deals from

Cincinnati

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

Prices updated today

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 Cincinnati to Chicago

Explore current cheapest deals departing from Cincinnati to Chicago

2026-09-24 – 2026-09-28
CVG - Chicago
74% AI deal score
$281
$153
Round trip
2026-09-23 – 2026-09-24
CVG - Chicago
74% AI deal score
$280
$154
Round trip
2026-09-29 – 2026-09-30
CVG - Chicago
42% AI deal score
$139
$155
Round trip
2026-09-14 – 2026-09-15
CVG - Chicago
43% AI deal score
$150
$155
Round trip
2026-09-23 – 2026-09-24
CVG - Chicago
42% AI deal score
$139
$155
Round trip
2026-09-15 – 2026-09-16
CVG - Chicago
43% AI deal score
$148
$155
Round trip
2026-09-24 – 2026-09-28
CVG - Chicago
42% AI deal score
$139
$155
Round trip
2026-10-17 – 2026-10-20
CVG - Chicago
46% AI deal score
$185
$155
Round trip
2026-10-01 – 2026-10-05
CVG - Chicago
44% AI deal score
$160
$155
Round trip
2026-10-05 – 2026-10-07
CVG - Chicago
44% AI deal score
$160
$155
Round trip

Cincinnati to Chicago: Overview

Insights for flights from Cincinnati to Chicago

For cheap flights from Cincinnati to Chicago, fares typically range from $240–$502, with a median of $317. Right now, current fares are above the typical level. Only 1% of recent fares were classified as a good price, indicating that finding a low fare may require some flexibility.

When considering the cheapest time to fly from Cincinnati to Chicago, April stands out with a median fare of $207. March also offers competitive pricing, with a median fare of $221. Additionally, September presents another opportunity for lower fares, with a median of $227.

A typical journey from Cincinnati to Chicago, including connections, takes about 1h 37m. This duration reflects the overall travel time for most itineraries on this route. While the non-stop flight time is also 1h 37m, connecting itineraries have a significantly longer median duration of 12h 38m.

The route from Cincinnati to Chicago covers a distance of 401 kilometers. This classifies it as a short-haul flight, meaning you can expect a relatively quick journey. Most itineraries on this route connect at least once, with a median of 2 stopovers when connecting, as only 36.6% of recent fares were for direct flights from Cincinnati to Chicago.

How much is a round trip from Cincinnati to Chicago

Regular price: $227 - $298

Prices for flights from Cincinnati to Chicago are currently below the regular range.

The regular price range for flights from Cincinnati to Chicago is between $227 and $298. The current lowest deal is $153 with Frontier Airlines for travel from Sep 24-Sep 28.

now $153

Low $227

High $298

The cheapest time to fly from Cincinnati to Chicago

The cheapest month to fly from Cincinnati to Chicago is December, with a median price of $226. The most expensive month is July, with a median price of $432. Prices are generally lower from June to December.

December

Cheapest

Flights from $226

July

Most Expensive

Flights from $432

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Cincinnati to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Cincinnati to Chicago

Tue, Sep 1

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$473

$309

One-way

Tue, Sep 1

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

$502

$444

One-way

Wed, Sep 2

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$365

$310

One-way

Wed, Sep 2

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$446

$320

One-way

Thu, Sep 3

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

Frontier Airlines

$476

$347

One-way

Fri, Sep 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$455

$317

One-way

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

2 nights

Aug 25 - Aug 27

$600 → $338

44%

2 nights

Aug 28 - Aug 30

$577 → $350

39%

3 nights

Aug 24 - Aug 27

$572 → $348

39%

1 night

Aug 26 - Aug 27

$572 → $348

39%

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Cincinnati to Chicago are above the typical level for this route.

📅 Best time to fly

Fly in April for the best prices

Historically, April, March, and September offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 1h 37m

The median flight time for a direct flight to Chicago is 1 hour and 37 minutes.

✈️ Airlines & availability

Connecting flights are common

Connecting flights make up 63.4% of recent deals, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines has a recent deal

A recent deal from Frontier Airlines was found for $153 from CVG to CHI.

🎯 Booking tip

Deals appear frequently

Deals for flights from Cincinnati to Chicago appear frequently, typically every 30 days.

Cincinnati main airports to depart from

Cincinnati/Northern Kentucky International (CVG)

Cheapest

Cincinnati/Northern Kentucky International Airport is a convenient departure point for flights to Chicago.

📍 ~15 km from Cincinnati (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Cincinnati.

📍 ~25 km from Chicago city center (reachable by car, train, or bus).

💸 Flights from ~$148

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 car or train)

💸 Flights from ~$247

Business & First Class Flight Deals to Chicago

73% AI deal score

$492

$357

Save $135

United Airlines

Business Class

From CVG

Elite

Nov 10

Chicago, United States

73% AI deal score

$493

$357

Save $136

United Airlines

Business Class

From CVG

Elite

Oct 22

Chicago, United States

72% AI deal score

$466

$357

Save $109

United Airlines

Business Class

From CVG

Elite

Oct 03

Chicago, United States

72% AI deal score

$472

$357

Save $115

United Airlines

Business Class

From CVG

Elite

Sep 29

Chicago, United States

72% AI deal score

$483

$357

Save $126

United Airlines

Business Class

From CVG

Chicago, United States

71% AI deal score

$446

$357

Save $89

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Cincinnati to Chicago is typically 14-27 days before departure. During this period, the average price observed was $209. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging $581. Conversely, booking too far in advance, such as 60+ days out, also shows higher average prices, around $389, across the trailing quarter.

Across the trailing 90 days, a good price for a flight from Cincinnati to Chicago is considered to be $240 or less. The median price for this route historically stands at $317. Prices can go up significantly, with 75% of observed prices being $502 or more. Travelers aiming for a more economical trip should target prices at or below the $240 threshold.

Historically, the cheapest months to fly from Cincinnati to Chicago are April, March, and September. In April, the median price was $207, while March saw a median of $221, and September had a median of $227. The annual median price for this route is $317. Based on data from the trailing 270 days, these months offer more budget-friendly options for travelers.

Related routes

More routes from Cincinnati

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Flights to Chicago from other cities

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Cincinnati to Chicago: Overview

Insights for flights from Cincinnati to Chicago

How much is a round trip from Cincinnati to Chicago

Regular price: $227 - $298

Prices for flights from Cincinnati to Chicago are currently below the regular range.

The regular price range for flights from Cincinnati to Chicago is between $227 and $298. The current lowest deal is $153 with Frontier Airlines for travel from Sep 24-Sep 28.

now $153

Low $227

High $298

The cheapest time to fly from Cincinnati to Chicago

December

Cheapest

Flights from $226

July

Most Expensive

Flights from $432

Jan

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Cincinnati to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Cincinnati to Chicago

Tue, Sep 1

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$473

$309

One-way

Tue, Sep 1

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

$502

$444

One-way

Wed, Sep 2

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$365

$310

One-way

Wed, Sep 2

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$446

$320

One-way

Thu, Sep 3

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

Frontier Airlines

$476

$347

One-way

Fri, Sep 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$455

$317

One-way

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

2 nights

Aug 25 - Aug 27

$600 → $338

44%

2 nights

Aug 28 - Aug 30

$577 → $350

39%

3 nights

Aug 24 - Aug 27

$572 → $348

39%

1 night

Aug 26 - Aug 27

$572 → $348

39%

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Cincinnati to Chicago are above the typical level for this route.

📅 Best time to fly

Fly in April for the best prices

Historically, April, March, and September offer the lowest median prices for this route.

⏱️ Flight duration

Direct flights take 1h 37m

The median flight time for a direct flight to Chicago is 1 hour and 37 minutes.

✈️ Airlines & availability

Connecting flights are common

Connecting flights make up 63.4% of recent deals, with a median of 2 stopovers.

🏆 Airline highlight

Frontier Airlines has a recent deal

A recent deal from Frontier Airlines was found for $153 from CVG to CHI.

🎯 Booking tip

Deals appear frequently

Deals for flights from Cincinnati to Chicago appear frequently, typically every 30 days.

Cincinnati main airports to depart from

Cincinnati/Northern Kentucky International (CVG)

Cheapest

Cincinnati/Northern Kentucky International Airport is a convenient departure point for flights to Chicago.

📍 ~15 km from Cincinnati (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

O Hare International (ORD)

Cheapest

O'Hare International Airport is a major hub for flights to Chicago from Cincinnati.

📍 ~25 km from Chicago city center (reachable by car, train, or bus).

💸 Flights from ~$148

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 car or train)

💸 Flights from ~$247

Chicago, United States

72% AI deal score

$1,445

$602

Save $843

From CVG

Elite

Oct 08

Chicago, United States

71% AI deal score

$448

$357

Save $91

United Airlines

Business Class

From CVG

Elite

Sep 28

Chicago, United States

71% AI deal score

$449

$357

Save $92

United Airlines

Business Class

From CVG

Elite

Oct 14

Chicago, United States

71% AI deal score

$446

$357

Save $89

United Airlines

Business Class

Frequently Asked Questions About Flights to Chicago

Cheap Flights from Cincinnati to Chicago

Today’s best flight deals from Cincinnati to Chicago

Cincinnati to Chicago: Overview

Insights for flights from Cincinnati to Chicago

How much is a round trip from Cincinnati to Chicago

The cheapest time to fly from Cincinnati to Chicago

Direct flights from Cincinnati to Chicago

Last-minute flights going from Cincinnati to Chicago

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

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights take 1h 37m

Connecting flights are common

Frontier Airlines has a recent deal

Deals appear frequently

Cincinnati 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

Oct 24

Aug 28

Aug 29

Sep 14

Nov 10

Oct 22

Oct 03

Sep 29

Nov 12

Oct 08

Sep 28

Oct 14

Frequently Asked Questions About Flights to Chicago

When should I buy Cincinnati to Chicago tickets?

What is a good price for a flight from Cincinnati to Chicago?

When is the cheapest time of year to fly from Cincinnati to Chicago?

Can I fly direct from Cincinnati to Chicago?

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

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

Related routes

More routes from Cincinnati

Flights to Chicago from other cities

Cincinnati to Chicago: Overview

Insights for flights from Cincinnati to Chicago

How much is a round trip from Cincinnati to Chicago

The cheapest time to fly from Cincinnati to Chicago

Direct flights from Cincinnati to Chicago

Last-minute flights going from Cincinnati to Chicago

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

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

Recent fares are above the typical level

Fly in April for the best prices

Direct flights take 1h 37m

Connecting flights are common

Frontier Airlines has a recent deal

Deals appear frequently

Cincinnati 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

Oct 24

Aug 28

Aug 29

Sep 14

Nov 10

Oct 22

Oct 03

Sep 29

Nov 12

Oct 08

Sep 28

Oct 14

Frequently Asked Questions About Flights to Chicago

When should I buy Cincinnati to Chicago tickets?

What is a good price for a flight from Cincinnati to Chicago?

When is the cheapest time of year to fly from Cincinnati to Chicago?