What is the cheapest airline that flies from Chicago to Kentucky?

Southwest, Delta, and United Airlines are the most popular carriers operating from Chicago to Kentucky

How many flights depart from Chicago to Kentucky on average per day?

As of March 2026, there are 182 flights per day flying from Chicago to Kentucky. The most common time of day flights depart is 5:00PM, with 40% of flights taking off in the evening.

How many flights depart from Chicago to Kentucky on average per week?

1,278 flights are operational weekly from Chicago to Kentucky as of March 2026. The most popular departure day for this route is Fri, with 17% of flights per week taking off on this day.

What airlines fly to Kentucky?

United Airlines, American Airlines and Contour are the top three most popular airlines that fly to Kentucky from Chicago according to our data. United Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Kentucky. Keep in mind that there are 4 different airlines that fly to Kentucky on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Chicago to Kentucky?

Prices for flights from Chicago to Kentucky were last updated today.

How many operators does momondo search for flights from Chicago to Kentucky?

The number of operators available for flights from Chicago to Kentucky is 7 as of March 2026.

How old do you have to be to fly from Chicago to Kentucky?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Kentucky.

What documentation or ID do you need to fly to Kentucky?

The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$63 Cheap Flights from Chicago to Kentucky in 2026

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Chicago to Kentucky

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:27 pm - 8:42 pm

ORD

TYS

30h 15m

1 stop

4:25 pm - 12:24 am

TYS

ORD

8h 59m

1 stop

$197Multiple Airlines

Wed, Apr 15 - Wed, Apr 22

9:30 pm - 7:31 pm

MDW

TYS

21h 01m

1 stop

1:22 pm - 1:57 pm

TYS

MDW

1h 35mnonstop

$199Allegiant Air

Mon, May 25 - Thu, May 28

2:40 pm - 7:40 pm

ORD

TYS

4h 00m

1 stop

6:40 am - 3:30 pm

TYS

ORD

9h 50m

1 stop

$204Southwest

Tue, Apr 21 - Sat, Apr 25

6:04 pm - 4:58 pm

ORD

BNA

22h 54m

1 stop

2:00 pm - 12:59 am

BNA

ORD

10h 59m

1 stop

$212Frontier

Fri, Apr 17 - Mon, Apr 20

6:04 pm - 4:58 pm

ORD

BNA

22h 54m

1 stop

2:00 pm - 12:59 am

BNA

ORD

10h 59m

1 stop

$216Frontier

Fri, Apr 17 - Mon, Apr 20

4:50 pm - 9:15 pm

MDW

CVG

3h 25m

1 stop

8:20 pm - 8:30 pm

CVG

MDW

1h 10mnonstop

$225Southwest

Tue, May 19 - Thu, May 21

6:00 am - 8:19 am

ORD

CVG

1h 19mnonstop

8:00 pm - 8:43 pm

CVG

ORD

1h 43mnonstop

$229United Airlines

Fri, May 1 - Tue, May 5

6:41 pm - 11:56 pm

ORD

CVG

4h 15m

1 stop

3:08 pm - 3:49 pm

CVG

ORD

1h 41mnonstop

$231American Airlines

Mon, Apr 13 - Sat, Apr 18

3:49 pm - 6:31 pm

ORD

SDF

1h 42mnonstop

7:52 pm - 11:54 pm

SDF

ORD

5h 02m

1 stop

$241American Airlines

Sun, May 10 - Sun, May 10

2:10 pm - 4:41 pm

ORD

SDF

1h 31mnonstop

9:07 am - 9:47 am

SDF

ORD

1h 40mnonstop

$257United Airlines

Wed, Apr 15 - Wed, Apr 22

Frontier flights from Chicago to Kentucky

Our best Frontier deals on Chicago to Kentucky flight tickets

Frontier

Apr 17

ORD6:04 pmChicago O'Hare Intl

22h 54m

1 stop

BNA4:58 pmNashville Intl

Apr 20

BNA2:00 pmNashville Intl

10h 59m

1 stop

ORD12:59 amChicago O'Hare Intl

$212

Frontier

Apr 17

ORD6:04 pmChicago O'Hare Intl

22h 54m

1 stop

BNA4:58 pmNashville Intl

Apr 20

BNA2:00 pmNashville Intl

10h 59m

1 stop

ORD12:59 amChicago O'Hare Intl

$216

Frontier

May 1

MDW6:00 amChicago Midway

11h 36m

1 stop

CVG6:36 pmCincinnati Cinci./N. Kentucky

May 5

CVG1:48 pmCincinnati Cinci./N. Kentucky

22h 21m

2 stops

MDW11:09 amChicago Midway

$224

Spirit Airlines flights from Chicago to Kentucky

Our best Spirit Airlines deals on Chicago to Kentucky flight tickets

Spirit Airlines

Apr 8

ORD5:05 amChicago O'Hare Intl

8h 24m

1 stop

BNA1:29 pmNashville Intl

Apr 10

BNA2:27 pmNashville Intl

8h 50m

1 stop

ORD11:17 pmChicago O'Hare Intl

$214

Spirit Airlines

Apr 13

ORD12:45 pmChicago O'Hare Intl

7h 01m

1 stop

BNA7:46 pmNashville Intl

Apr 15

BNA3:27 pmNashville Intl

8h 57m

1 stop

ORD12:24 amChicago O'Hare Intl

$220

Spirit Airlines

Apr 8

ORD7:17 amChicago O'Hare Intl

6h 12m

1 stop

BNA1:29 pmNashville Intl

Apr 10

BNA2:27 pmNashville Intl

8h 50m

1 stop

ORD11:17 pmChicago O'Hare Intl

$221

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKnoxville

ORD - TYS

ORDTYS

Chicago O'Hare Intl

Wed 4/15

1:27 pm-8:42 pm

1 stop30h 15m

Knoxville McGhee Tyson

Wed 4/22

4:25 pm-12:24 am

1 stop8h 59m

$197

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Mon 5/25

9:30 pm-7:31 pm

1 stop21h 01m

Knoxville McGhee Tyson

Thu 5/28

1:22 pm-1:57 pm

Nonstop1h 35m

$199

ChicagoKnoxville

ORD - TYS

ORDTYS

Chicago O'Hare Intl

Tue 4/21

2:40 pm-7:40 pm

1 stop4h 00m

Knoxville McGhee Tyson

Sat 4/25

6:40 am-3:30 pm

1 stop9h 50m

$204

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 4/17

6:04 pm-4:58 pm

1 stop22h 54m

Nashville Intl

Mon 4/20

2:00 pm-12:59 am

1 stop10h 59m

$212

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 4/17

6:04 pm-4:58 pm

1 stop22h 54m

Nashville Intl

Mon 4/20

2:00 pm-12:59 am

1 stop10h 59m

$216

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 5/19

4:50 pm-9:15 pm

1 stop3h 25m

Cincinnati Cinci./N. Kentucky

Thu 5/21

8:20 pm-8:30 pm

Nonstop1h 10m

$225

Quickest round-trip

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Fri 5/1

6:00 am-8:19 am

Nonstop1h 19m

Cincinnati Cinci./N. Kentucky

Tue 5/5

8:00 pm-8:43 pm

Nonstop1h 43m

$229

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Mon 4/13

6:41 pm-11:56 pm

1 stop4h 15m

Cincinnati Cinci./N. Kentucky

Sat 4/18

3:08 pm-3:49 pm

Nonstop1h 41m

$231

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sun 5/10

3:49 pm-6:31 pm

Nonstop1h 42m

Louisville Intl

Sun 5/10

7:52 pm-11:54 pm

1 stop5h 02m

$241

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 4/15

2:10 pm-4:41 pm

Nonstop1h 31m

Louisville Intl

Wed 4/22

9:07 am-9:47 am

Nonstop1h 40m

$257

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago to Kentucky

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in August, then September is your next best option. Flight prices from Chicago to Kentucky during September average around $225.

What is the cheapest day to depart on your flight to Kentucky?

Our data shows that Saturday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $255. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $471. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.

What is the cheapest time of day to depart on your flight to Kentucky?

According to our data, the cheapest time of day to fly to Kentucky is in the morning. momondo users have found flights departing from Chicago to Kentucky in the morning for as low as $293. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Kentucky is in the afternoon when prices are around $339.

What is the cheapest Chicago to Kentucky flight route?

Fly from Chicago O'Hare Intl to Owensboro Daviess County for the best Chicago - Kentucky flight prices

How far in advance should I book a flight to Kentucky?

You are more likely to see cheaper flights to Kentucky from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Kentucky for around $326 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kentucky from Chicago for as low as $135 on momondo.

What cabin class options are available on Chicago to Kentucky flights?

There are 4 cabin classes available to choose from on Chicago to Kentucky flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Kentucky flights?

No. A direct flight is the cheapest option for a flight between Chicago to Kentucky.

Cheap Chicago to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kentucky

Best Price Found	$59
Fastest flight time	1h 05m
Direct flights	Every day
Airports in Kentucky	43 airports

The best one-way flight to Kentucky from Chicago in the past 72 hours is $59. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $158.

The fastest flight from Chicago to Kentucky takes 1h 05m

Direct flights go from Chicago to Kentucky every day.

There are 43 airports in Kentucky. From Chicago there are direct flights to Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG).

Search flight deals

When did momondo last update prices for flights from Chicago to Kentucky?
Prices for flights from Chicago to Kentucky were last updated today.
How many operators does momondo search for flights from Chicago to Kentucky?
The number of operators available for flights from Chicago to Kentucky is 7 as of March 2026.
How old do you have to be to fly from Chicago to Kentucky?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Kentucky.
What documentation or ID do you need to fly to Kentucky?
The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Kentucky?
Based on momondo bookings for flights between Chicago and Kentucky, the leading plane model is Canadair (Bombardier) Regional Jet CRJ-550, making up 22.50% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 19.72%, Embraer 175 with 18.74%, and Embraer 170 with 11.95%.

Best airlines flying from Chicago to Kentucky

Compare and see reviews for airlines that fly from Chicago to Kentucky with momondo

Airline	Rating	Free Cancellation	Price
Contour	PriceFrom $108	Free Cancellation	Rating 7.6 42 reviews	Search Contour flights
Southwest	PriceFrom $124	Free Cancellation	Rating 8.0 4,324 reviews	Search Southwest flights
United Airlines	PriceFrom $133	Free Cancellation	Rating 7.4 9,459 reviews	Search United Airlines flights
American Airlines	PriceFrom $136	Free Cancellation	Rating 7.1 11,486 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kentucky?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Kentucky from Chicago.

Can I find flights from Chicago to Kentucky with flexible booking policies on momondo?

momondo does allow users to show only those flights to Kentucky from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Kentucky?

Once all potential Chicago to Kentucky flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Kentucky right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Kentucky flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Kentucky trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Wed 4/22

Wed 4/29

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Kentucky

Popular cities

Other flights from Chicago

Other flights to Kentucky

Airlines

Complete your trip

Feeling lucky

Popular cities in Kentucky

Flights to New Yorkfrom $66

Flights to Los Angelesfrom $57

Flights to Orlandofrom $47

Flights to Miamifrom $53

Flights to Chicagofrom $66

Flights to San Franciscofrom $84

Flights to Las Vegasfrom $57

Flights to Washington, D.C.from $59

Flights to Bostonfrom $70

Flights to Atlantafrom $49

Flights to Dallasfrom $60

Flights to Seattlefrom $71

Cheap flights from Chicago to Kentucky from $63

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kentucky departing on 6/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to Kentucky

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago to Kentucky

Our best Frontier deals on Chicago to Kentucky flight tickets

Spirit Airlines flights from Chicago to Kentucky

Our best Spirit Airlines deals on Chicago to Kentucky flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.

See travel insights to Kentucky from

How to get the cheapest flight ticket from Chicago to Kentucky

What is the cheapest month to fly to Kentucky?

What is the cheapest day to depart on your flight to Kentucky?

What is the cheapest time of day to depart on your flight to Kentucky?

What is the cheapest Chicago to Kentucky flight route?

How far in advance should I book a flight to Kentucky?

What cabin class options are available on Chicago to Kentucky flights?

Can stopping save me money on Chicago to Kentucky flights?

What is the cheapest airline that flies from Chicago to Kentucky?

What airlines fly to Kentucky?

How many flights depart from Chicago to Kentucky on average per day?

How many flights depart from Chicago to Kentucky on average per week?

Cheap Chicago to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kentucky

Best Price Found

Fastest flight time

Direct flights

Airports in Kentucky

Best airlines flying from Chicago to Kentucky

Compare and see reviews for airlines that fly from Chicago to Kentucky with momondo

Why use momondo?

An easier way to manage your Kentucky trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Kentucky

Popular cities in Kentucky

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

Kentucky flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to Kentucky

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Complete your trip to Kentucky

Explore popular destinations other users love

According to popular flight searches on momondo this year