What is the cheapest airline that flies from Chicago O'Hare Intl to Kentucky?

Spirit Airlines, United Airlines, and American Airlines are the most popular carriers operating from Chicago O'Hare Intl to Kentucky

How many flights depart from Chicago O'Hare Intl Airport to Kentucky on average per day?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 117 per day as of December 2025. The most frequent departure time is 10:00AM, with 42% of daily flights leaving in the evening.

What airlines fly to Kentucky?

American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Kentucky from Chicago O'Hare Intl Airport according to our data. American Airlines is the first choice among our users, with 48% of people opting to fly with this airline when traveling to Kentucky. Keep in mind that there are 3 different airlines that fly to Kentucky on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago O'Hare Intl Airport to Kentucky on average per week?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 823 per week as of December 2025. The most frequent departure day is Tue, with 22% of weekly flights leaving on this day.

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Kentucky?

Prices for flights from Chicago O'Hare Intl Airport to Kentucky are updated daily.

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Kentucky?

There are 6 operators available for flights from Chicago O'Hare Intl Airport to Kentucky as of December 2025.

How old do you have to be to fly from Chicago O'Hare Intl Airport to Kentucky?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Kentucky.

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

The travel and health documents you'll need for your trip to Kentucky may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kentucky. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$58 Cheap Flights from Chicago O'Hare Intl Airport to Kentucky in 2025/26

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Find the cheapest flights from Chicago O'Hare Intl Airport to Kentucky

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

10:55 am - 12:25 pm

ORD

OWB

1h 30mnonstop

3:10 pm - 4:45 pm

OWB

ORD

1h 35mnonstop

$105Contour

Mon, Jan 5 - Fri, Jan 9

10:55 am - 12:25 pm

ORD

OWB

1h 30mnonstop

8:40 am - 10:15 am

OWB

ORD

1h 35mnonstop

$119Contour

Thu, Feb 5 - Mon, Feb 9

8:43 pm - 7:25 am

ORD

BNA

10h 42m1 stop

8:12 pm - 11:22 am

BNA

ORD

15h 10m1 stop

$129Spirit Airlines

Fri, Jan 23 - Mon, Jan 26

7:52 pm - 10:30 pm

ORD

SDF

1h 38mnonstop

2:05 pm - 2:49 pm

SDF

ORD

1h 44mnonstop

$133United Airlines

Tue, Jan 20 - Wed, Jan 21

8:49 pm - 11:19 pm

ORD

SDF

1h 30mnonstop

1:32 pm - 2:20 pm

SDF

ORD

1h 48mnonstop

$134American Airlines

Wed, Feb 4 - Wed, Feb 11

12:00 pm - 7:43 pm

ORD

BNA

7h 43m1 stop

8:40 am - 9:03 pm

BNA

ORD

12h 23m1 stop

$137Multiple Airlines

Sat, Jan 31 - Mon, Feb 2

8:43 pm - 7:25 am

ORD

BNA

10h 42m1 stop

8:40 am - 9:03 pm

BNA

ORD

12h 23m1 stop

$139Spirit Airlines

Fri, Jan 30 - Mon, Feb 2

12:42 pm - 7:25 am

ORD

BNA

18h 43m2 stops

8:12 pm - 10:36 pm

BNA

ORD

26h 24m1 stop

$146Multiple Airlines

Wed, Jan 14 - Wed, Jan 21

4:08 pm - 6:39 pm

ORD

SDF

1h 31mnonstop

8:06 am - 8:59 am

SDF

ORD

1h 53mnonstop

$152American Airlines

Tue, Jan 13 - Thu, Jan 15

7:52 pm - 10:30 pm

ORD

SDF

1h 38mnonstop

8:29 am - 9:13 am

SDF

ORD

1h 44mnonstop

$171United Airlines

Mon, Jan 19 - Mon, Jan 26

American Airlines flights from Chicago O'Hare Intl Airport to Kentucky

Our best American Airlines deals on Chicago O'Hare Intl Airport to Kentucky flight tickets

American Airlines

Feb 4

ORD8:49 pmChicago O'Hare Intl

1h 30m

SDF11:19 pmLouisville Intl

Feb 11

SDF1:32 pmLouisville Intl

1h 48m

ORD2:20 pmChicago O'Hare Intl

$134

Find similar

American Airlines

Jan 13

ORD10:01 amChicago O'Hare Intl

1h 31m

SDF12:32 pmLouisville Intl

Jan 15

SDF8:06 amLouisville Intl

1h 53m

ORD8:59 amChicago O'Hare Intl

$152

Find similar

American Airlines

Feb 21

ORD1:47 pmChicago O'Hare Intl

1h 23m

LEX4:10 pmLexington Blue Grass

Mar 14

LEX4:59 pmLexington Blue Grass

1h 43m

ORD5:42 pmChicago O'Hare Intl

$190

Find similar

Spirit Airlines flights from Chicago O'Hare Intl Airport to Kentucky

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Kentucky flight tickets

Spirit Airlines

Jan 23

ORD8:43 pmChicago O'Hare Intl

10h 42m

1 stop

BNA7:25 amNashville Intl

Jan 26

BNA8:12 pmNashville Intl

15h 10m

1 stop

ORD11:22 amChicago O'Hare Intl

$129

Find similar

Spirit Airlines

Jan 30

ORD8:43 pmChicago O'Hare Intl

10h 42m

1 stop

BNA7:25 amNashville Intl

Feb 2

BNA8:40 amNashville Intl

12h 23m

1 stop

ORD9:03 pmChicago O'Hare Intl

$139

Find similar

Spirit Airlines

Jan 19

ORD12:44 pmChicago O'Hare Intl

19h 45m

1 stop

BNA8:29 amNashville Intl

Jan 26

BNA8:12 pmNashville Intl

15h 10m

1 stop

ORD11:22 amChicago O'Hare Intl

$142

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Mon 1/5

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Fri 1/9

3:10 pm-4:45 pm

Nonstop1h 35m

$105

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 2/5

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 2/9

8:40 am-10:15 am

Nonstop1h 35m

$119

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 1/23

8:43 pm-7:25 am

1 stop10h 42m

Nashville Intl

Mon 1/26

8:12 pm-11:22 am

1 stop15h 10m

$129

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 1/20

7:52 pm-10:30 pm

Nonstop1h 38m

Louisville Intl

Wed 1/21

2:05 pm-2:49 pm

Nonstop1h 44m

$133

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 2/4

8:49 pm-11:19 pm

Nonstop1h 30m

Louisville Intl

Wed 2/11

1:32 pm-2:20 pm

Nonstop1h 48m

$134

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 1/31

12:00 pm-7:43 pm

1 stop7h 43m

Nashville Intl

Mon 2/2

8:40 am-9:03 pm

1 stop12h 23m

$137

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 1/30

8:43 pm-7:25 am

1 stop10h 42m

Nashville Intl

Mon 2/2

8:40 am-9:03 pm

1 stop12h 23m

$139

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 1/14

12:42 pm-7:25 am

2 stops18h 43m

Nashville Intl

Wed 1/21

8:12 pm-10:36 pm

1 stop26h 24m

$146

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 1/13

4:08 pm-6:39 pm

Nonstop1h 31m

Louisville Intl

Thu 1/15

8:06 am-8:59 am

Nonstop1h 53m

$152

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Mon 1/19

7:52 pm-10:30 pm

Nonstop1h 38m

Louisville Intl

Mon 1/26

8:29 am-9:13 am

Nonstop1h 44m

$171

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Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport 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 January is your next best option. Flight prices from Chicago O'Hare Intl Airport to Kentucky during January average around $257.

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 $249. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $392. 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 evening. momondo users have found flights departing from Chicago O'Hare Intl Airport to Kentucky in the evening for as low as $286. 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 at noon when prices are around $307.

What is the cheapest Chicago O'Hare Intl to Kentucky flight route?

Fly from Chicago O'Hare Intl to Owensboro Daviess County for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Kentucky for around $310 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kentucky from Chicago O'Hare Intl Airport for as low as $185 on momondo.

What cabin class options are available on Chicago O'Hare Intl to Kentucky flights?

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

Cheap Chicago O'Hare Intl Airport to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Kentucky

Best Price Found	$128
Fastest flight time	1h 22m
Direct flights	Every day
Airports in Kentucky	43 airports

The best one-way flight to Kentucky from Chicago O'Hare Intl Airport in the past 72 hours is $128. The best round-trip flight deal from Chicago O'Hare Intl Airport to Kentucky found on momondo in the last 72 hours is $109.

The fastest flight from Chicago O'Hare Intl Airport to Kentucky takes 1h 22m

Direct flights go from Chicago O'Hare Intl Airport to Kentucky every day.

There are 43 airports in Kentucky. From Chicago O'Hare Intl Airport there are direct flights to Evansville Dress Regional (EVV), Louisville Intl (SDF), Nashville Intl (BNA), Cincinnati Cinci./N. Kentucky (CVG) and 2 more.

Search flight deals

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Kentucky?
Prices for flights from Chicago O'Hare Intl Airport to Kentucky are updated daily.
How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Kentucky?
There are 6 operators available for flights from Chicago O'Hare Intl Airport to Kentucky as of December 2025.
How old do you have to be to fly from Chicago O'Hare Intl Airport to Kentucky?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Kentucky.
What documentation or ID do you need to fly to Kentucky?
The travel and health documents you'll need for your trip to Kentucky may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kentucky. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago O'Hare Intl Airport to Kentucky?
momondo data reveals that the most frequently booked plane model on the route from Chicago O'Hare Intl Airport to Kentucky is Embraer 175 (Enhanced Winglets), representing 23.12% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet CRJ-550 at 22.69%, Embraer 175 at 15.17%, and Canadair (Bombardier) Regional Jet 700 at 10.26%.

Best airlines flying from Chicago O'Hare Intl Airport to Kentucky

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Kentucky with momondo

Airline	Rating	Free Cancellation	Price
Contour	PriceFrom $126	Free Cancellation	Rating 7.6 43 reviews	Search Contour flights
United Airlines	PriceFrom $127	Free Cancellation	Rating 7.4 9,109 reviews	Search United Airlines flights
American Airlines	PriceFrom $136	Free Cancellation	Rating 7.2 11,050 reviews	Search American Airlines flights

Why use momondo?

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

It is quick and easy to find Chicago to Kentucky flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Kentucky that suits you.

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

Flights from Chicago to Kentucky with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Chicago to Kentucky flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are not ready to book a flight from Chicago to Kentucky now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Kentucky and let you know when they change.

An easier way to manage your Kentucky trip

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Popular cities in Kentucky

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Chicago O'Hare Intl Airport flight routes

Flights from Chicago O'Hare Intl to Baltimore/Washington

Flights from Chicago O'Hare Intl to Charlotte Douglas

Flights from Chicago O'Hare Intl to Atlanta Hartsfield-Jackson

Flights from Chicago O'Hare Intl to New York John F Kennedy Intl

Flights from Chicago O'Hare Intl to Austin Bergstrom

Flights from Chicago O'Hare Intl to Philadelphia

Cheap flights from Chicago O'Hare Intl Airport to Kentucky from $58

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Big names and deals

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Find the cheapest flights from Chicago O'Hare Intl Airport to Kentucky

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American Airlines flights from Chicago O'Hare Intl Airport to Kentucky

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Spirit Airlines flights from Chicago O'Hare Intl Airport to Kentucky

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Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Kentucky that are best for you.

See travel insights to Kentucky from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Kentucky

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in August, then January is your next best option. Flight prices from Chicago O'Hare Intl Airport to Kentucky during January average around $257.

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 O'Hare Intl to Kentucky flight route?

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

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

What cabin class options are available on Chicago O'Hare Intl to Kentucky flights?

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

What is the cheapest airline that flies from Chicago O'Hare Intl to Kentucky?

Spirit Airlines, United Airlines, and American Airlines are the most popular carriers operating from Chicago O'Hare Intl to Kentucky

What airlines fly to Kentucky?

How many flights depart from Chicago O'Hare Intl Airport to Kentucky on average per day?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 117 per day as of December 2025. The most frequent departure time is 10:00AM, with 42% of daily flights leaving in the evening.

How many flights depart from Chicago O'Hare Intl Airport to Kentucky on average per week?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 823 per week as of December 2025. The most frequent departure day is Tue, with 22% of weekly flights leaving on this day.

Cheap Chicago O'Hare Intl Airport to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Kentucky

Best Price Found

Fastest flight time

Direct flights

Airports in Kentucky

When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Kentucky?

How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Kentucky?

How old do you have to be to fly from Chicago O'Hare Intl Airport to Kentucky?

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

What is the most popular plane model from Chicago O'Hare Intl Airport to Kentucky?

Best airlines flying from Chicago O'Hare Intl Airport to Kentucky

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Kentucky with momondo

Why use momondo?

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

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

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

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

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