To Chicago

Cheap Flights from Cincinnati to Chicago

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Cincinnati

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

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 Cincinnati to Chicago

Explore current cheapest deals departing from Cincinnati to Chicago

Round trip

Sort by: Cheapest

July 14 - July 21

Cheapest

Earliest

CVG - Chicago

$142

$157

Round trip

July 14 - July 28

Cheapest

Earliest

CVG - Chicago

$126

$157

Round trip

July 21 - July 28

Cheapest

CVG - Chicago

$139

$157

Round trip

July 22 - July 29

Cheapest

CVG - Chicago

$139

$157

Round trip

July 14 - July 15

Cheapest

Earliest

CVG - Chicago

$166

$157

Round trip

September 1 - September 8

Cheapest

CVG - Chicago

$137

$157

Round trip

December 9 - December 16

Cheapest

CVG - Chicago

$189

$157

Round trip

July 14 - July 15

Cheapest

Best

Earliest

CVG - Chicago

$235

$157

Round trip

July 15 - July 22

Cheapest

CVG - Chicago

$142

$157

Round trip

July 22 - July 29

Cheapest

CVG - Chicago

$155

$157

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Cincinnati to Chicago

For cheap flights from Cincinnati to Chicago, fares typically range from $226–$419, with a median of $288. Right now, current fares are below the typical level, and about 3% of recent fares were classified as a good price. New deals appear almost daily for this route, offering frequent opportunities to find competitive pricing.

When is the cheapest time to fly from Cincinnati to Chicago? You'll find the lowest median fares in April, with prices averaging $207. March also offers more affordable options, with a median fare of $221. Following closely, September presents a median fare of $227, making these months generally more economical for travel.

A typical journey from Cincinnati to Chicago takes about 6h 9m, including connections. This duration reflects the overall travel time, as a meaningful share of itineraries are non-stop, while the rest connect once. When itineraries do include connections, the median number of stopovers is 2.

The route from Cincinnati to Chicago covers a distance of 401 km. This classifies it as a short-haul flight, meaning you can expect a relatively quick travel experience between these two cities.

How much is a round trip from Cincinnati to Chicago

Regular price: $115 - $265

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

The regular price range for flights from Cincinnati to Chicago is $115 to $265. The current lowest deal is $157 with United Airlines for travel from July 14 to July 21.

now $157

Low $115

High $265

The cheapest time to fly from Cincinnati to Chicago

The cheapest month to fly from Cincinnati to Chicago is April, with a median price of $207. The most expensive month is July, with a median price of $372. Prices are generally lower from January to November.

April

Cheapest

Flights from $207

July

Most Expensive

Flights from $372

Jan

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Direct flights from Cincinnati to Chicago

Southwest Airlines

United Airlines

Last-minute flights going from Cincinnati to Chicago

Fri, Jun 19

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$438

$381

One-way

Sat, Jun 20

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$439

$391

One-way

Mon, Jun 22

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$403

$333

One-way

Mon, Jun 22

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$396

$337

One-way

Wed, Jun 24

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (ORD)

Frontier Airlines

$325

$277

One-way

Wed, Jun 24

⌛ Last-Minute

CVG - Chicago

Cincinnati (CVG) - Chicago (MDW)

Frontier Airlines

$355

$291

One-way

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

3 nights

Oct 12 - Oct 15

$371 → $215

42%

3 nights

Oct 7 - Oct 10

$326 → $196

40%

3 nights

Aug 22 - Aug 25

$281 → $176

37%

3 nights

Aug 17 - Aug 20

$282 → $177

37%

Popular Airports to fly from Cincinnati to Chicago

Cincinnati - Chicago route insights

💸 Price insights

Recent fares are below the typical level.

Recent fares from Cincinnati to Chicago are below the typical level, with a median price of $288.

📅 Best time to fly

April is historically the cheapest month to fly.

Historically, April is the cheapest month to fly from Cincinnati to Chicago, with a median price of $207.

⏱️ Flight duration

Flights typically take 6h 9m.

The median flight duration from Cincinnati to Chicago is 6 hours and 9 minutes, including layovers.

✈️ Airlines & availability

Direct flights are available from 2 airlines.

Direct flights to Chicago are available from Southwest Airlines and United Airlines, accounting for 48.7% of deals.

🏆 Airline highlight

United Airlines offers a recent deal for $157.

United Airlines recently offered a deal for $157 from Cincinnati to Chicago, valid from Jul 14-Jul 21.

🎯 Booking tip

Deals are frequent, appearing daily.

Deals for flights from Cincinnati to Chicago are frequent, with over 1 deal appearing per day.

Cincinnati main airports to depart from

Cincinnati/Northern Kentucky International (CVG)

Cheapest

Cincinnati/Northern Kentucky International is a great option for flights from Cincinnati to Chicago.

📍 ~20 km from Cincinnati (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Fly into Chicago Midway International for convenient access to Chicago, often with competitive fares from Cincinnati.

📍 ~15 km from Chicago city center (reachable by car)

💸 Flights from ~$157

Chicago Rockford International (RFD)

Consider Chicago Rockford International for an alternative arrival option when flying to the Chicago area.

📍 ~100 km from Chicago city center (reachable by car)

💸 Flights from ~$196

O Hare International (ORD)

Choose O Hare International for a major hub arrival in Chicago, offering many connections from Cincinnati.

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

💸 Flights from ~$157

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers high-frequency flight options and direct rail access to Chicago.

📍 ~135 km from Chicago (reachable by rail; travel time can be affected by heavy traffic).

💸 Flights from ~$231

South Bend International (SBN)

Cheapest

South Bend International is the closest alternative to Chicago, with direct commuter rail links.

📍 ~120 km from Chicago (reachable by rail).

💸 Flights from ~$191

Gerald R. Ford International (GRR)

Gerald R. Ford International is a major regional hub, good for travelers on Chicago's eastern side.

📍 ~200 km from Chicago (requires a significant drive).

💸 Flights from ~$199

Dane County Regional (MSN)

Dane County Regional is a reliable, less congested alternative to Chicago or Milwaukee airports.

📍 ~200 km from Chicago.

💸 Flights from ~$272

Fort Wayne International (FWA)

Fort Wayne International offers regional service for travelers in Chicago's southeastern suburbs.

📍 ~220 km from Chicago (significant distance and limited flight frequency).

💸 Flights from ~$223

Business & First Class Flight Deals to Chicago

41% AI deal score

$1,982

From CVG

Elite

Jun 30

Chicago, United States

39% AI deal score

Chicago, United States

28% AI deal score

$1,821

From CVG

Elite

Jun 25

Chicago, United States

28% AI deal score

$2,106

Frequently Asked Questions About Flights to Chicago

Historically, the optimal time to purchase tickets 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 significantly higher for last-minute bookings, with flights purchased 0-6 days out averaging $581. For those planning further in advance, tickets bought 28-59 days out average $379, while those purchased 60+ days in advance average $389.

Across the trailing 90 days, a good price for a flight from Cincinnati to Chicago is considered to be $226 or less. The median price for this route historically stands at $288. Prices can go up to $419 or more for the higher end of the market. This threshold of $226 represents the lower quartile of prices observed for this route.

Historically, the cheapest months to fly from Cincinnati to Chicago are April, with a median price of $207, and March, with a median price of $221. September also offers competitive pricing, with a median of $227. The annual median price for this route is $288, indicating that these months offer notable savings compared to the overall average.

Related routes

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