Can I fly direct from Cincinnati to Chicago?

Yes, direct flights from Cincinnati to Chicago are available. Historically, approximately 36.6% of all flights on this route have been direct. For travelers who prefer not to have a direct flight, connecting flights typically involve a median of 2 stopovers. This indicates that while direct options are common, connecting flights are also a significant part of the available routes.

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 travel time is considerably longer, averaging 9 hours and 21 minutes. This significant difference highlights the efficiency of direct routes compared to those with connections. Travelers should factor in these durations when planning their journey.

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 one where deals are common. Travelers can typically find favorable prices with regularity across the trailing 30 days. This consistent availability makes it easier for passengers to find good value on their journey between these two cities.

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 14 days ago

406 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 2, 2026.)

Today’s best flight deals from Cincinnati to Chicago

Explore current cheapest deals departing from Cincinnati to Chicago

2026-09-28 – 2026-09-30
CVG - Chicago
71% AI deal score
$257
$125
Round trip
2026-09-28 – 2026-10-07
CVG - Chicago
75% AI deal score
$230
$125
Round trip
2026-09-28 – 2026-10-21
CVG - Chicago
73% AI deal score
$204
$126
Round trip
2026-10-12 – 2026-10-21
CVG - Chicago
75% AI deal score
$257
$128
Round trip
2026-08-31 – 2026-09-23
CVG - Chicago
73% AI deal score
$223
$130
Round trip
2026-08-31 – 2026-09-30
CVG - Chicago
73% AI deal score
$221
$131
Round trip
2026-08-31 – 2026-09-16
CVG - Chicago
73% AI deal score
$229
$131
Round trip
2026-08-31 – 2026-09-09
CVG - Chicago
75% AI deal score
$258
$131
Round trip
2026-08-31 – 2026-09-02
CVG - Chicago
72% AI deal score
$302
$131
Round trip
2026-09-23 – 2026-10-21
CVG - Chicago
70% AI deal score
$204
$142
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: $225 - $375

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

The regular price range for this route is typically between $225 and $375. The current lowest deal is $150 with Frontier Airlines for travel from Aug 29-Aug 31.

now $150

Low $225

High $375

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, Aug 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$550

$328

One-way

Tue, Aug 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$567

$332

One-way

Wed, Aug 5

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

Frontier Airlines

$559

$370

One-way

Mon, Aug 17

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$279

$193

One-way

Mon, Aug 17

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$312

$194

One-way

Tue, Aug 18

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$311

$190

One-way

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

1 night

Aug 10 - Aug 11

$595 → $326

45%

1 night

Aug 12 - Aug 13

$572 → $331

42%

4 nights

Aug 10 - Aug 14

$569 → $338

41%

3 nights

Aug 10 - Aug 13

$572 → $345

40%

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares are above the typical level for the CVG to CHI route.

📅 Best time to fly

Fly in December for the lowest prices.

Historically, December is the cheapest month to fly, with a median price of $226.

⏱️ Flight duration

Direct flights average 1h 37m.

Direct flights from Cincinnati to Chicago typically take 1h 37m.

✈️ Airlines & availability

Connecting flights are dominant.

About 36.6% of recent flights are direct, with connecting flights being more common.

🏆 Airline highlight

Frontier Airlines offers a recent deal.

Frontier Airlines had a recent deal for $150 from CVG to CHI.

🎯 Booking tip

Deals appear frequently on this route.

Deals from Cincinnati to Chicago appear frequently, offering more opportunities to save.

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

72% AI deal score

$486

$369

Save $117

United Airlines

Business Class

From CVG

Elite

Aug 13

Chicago, United States

72% AI deal score

$928

$667

Save $261

United Airlines

Business Class

From CVG

Elite

Sep 19

Chicago, United States

72% AI deal score

$1,222

$758

Save $464

From CVG

Elite

Aug 22

Chicago, United States

72% AI deal score

$1,594

$795

Save $799

From CVG

Elite

Oct 19

Chicago, United States

71% AI deal score

$481

$381

Save $100

United Airlines

Business Class

From CVG

Elite

Aug 11

Chicago, United States

71% AI deal score

$1,041

$661

Save $380

From CVG

Elite

Sep 05

Chicago, United States

69% AI deal score

$488

$357

Save $131

From CVG

Elite

Aug 24

Chicago, United States

69% AI deal score

$1,413

$836

Save $577

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 for a ticket is around $209. Prices tend to be higher for last-minute bookings, with flights purchased 0-6 days out averaging $581. For those planning further ahead, tickets bought 28-59 days in advance have an average price of $379, while those purchased 60+ days out average $389.

Across the trailing quarter, a good price for a flight from Cincinnati to Chicago is considered to be $240 or less. The median price for this route was $317 during the same period. Prices tend to increase significantly beyond this threshold, with 75% of tickets costing $502 or more. Travelers aiming for value should target fares at or below the $240 mark.

Historically, the cheapest months to fly from Cincinnati to Chicago include April, with a median price of $207, and March, with a median price of $221. September also shows competitive pricing, with a median of $227. While September is listed as both a cheaper month and the most expensive month, this indicates price variability within the month. The annual median price for this route is $317, suggesting that these months offer significant savings compared to the yearly average.

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: $225 - $375

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

The regular price range for this route is typically between $225 and $375. The current lowest deal is $150 with Frontier Airlines for travel from Aug 29-Aug 31.

now $150

Low $225

High $375

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, Aug 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$550

$328

One-way

Tue, Aug 4

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$567

$332

One-way

Wed, Aug 5

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

Frontier Airlines

$559

$370

One-way

Mon, Aug 17

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$279

$193

One-way

Mon, Aug 17

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$312

$194

One-way

Tue, Aug 18

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$311

$190

One-way

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

1 night

Aug 10 - Aug 11

$595 → $326

45%

1 night

Aug 12 - Aug 13

$572 → $331

42%

4 nights

Aug 10 - Aug 14

$569 → $338

41%

3 nights

Aug 10 - Aug 13

$572 → $345

40%

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares are above the typical level for the CVG to CHI route.

📅 Best time to fly

Fly in December for the lowest prices.

Historically, December is the cheapest month to fly, with a median price of $226.

⏱️ Flight duration

Direct flights average 1h 37m.

Direct flights from Cincinnati to Chicago typically take 1h 37m.

✈️ Airlines & availability

Connecting flights are dominant.

About 36.6% of recent flights are direct, with connecting flights being more common.

🏆 Airline highlight

Frontier Airlines offers a recent deal.

Frontier Airlines had a recent deal for $150 from CVG to CHI.

🎯 Booking tip

Deals appear frequently on this route.

Deals from Cincinnati to Chicago appear frequently, offering more opportunities to save.

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

$486

$369

Save $117

United Airlines

Business Class

From CVG

Elite

Aug 13

Chicago, United States

72% AI deal score

$928

$667

Save $261

United Airlines

Business Class

From CVG

Elite

Sep 19

Chicago, United States

72% AI deal score

$1,222

$758

Save $464

From CVG

Elite

Aug 22

Chicago, United States

72% AI deal score

$1,594

$795

Save $799

From CVG

Elite

Oct 19

Chicago, United States

71% AI deal score

$481

$381

Save $100

United Airlines

Business Class

From CVG

Elite

Aug 11

Chicago, United States

71% AI deal score

$1,041

$661

Save $380

From CVG

Elite

Sep 05

Chicago, United States

69% AI deal score

$488

$357

Save $131

From CVG

Elite

Aug 24

Chicago, United States

69% AI deal score

$1,413

$836

Save $577

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 December for the lowest prices.

Direct flights average 1h 37m.

Connecting flights are dominant.

Frontier Airlines offers a recent deal.

Deals appear frequently on this route.

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

Aug 20

Aug 26

Aug 22

Aug 13

Sep 03

Aug 13

Sep 19

Aug 22

Oct 19

Aug 11

Sep 05

Aug 24

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 December for the lowest prices.

Direct flights average 1h 37m.

Connecting flights are dominant.

Frontier Airlines offers a recent deal.

Deals appear frequently on this route.

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

Aug 20

Aug 26

Aug 22

Aug 13

Sep 03

Aug 13

Sep 19

Aug 22

Oct 19

Aug 11

Sep 05

Aug 24

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?