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 day?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 147 per day as of September 2025. The most frequent departure time is 8:00PM, with 41% of daily flights leaving in the evening.

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

Spirit Airlines, Frontier, and Southwest 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 week?

The number of flights available between Chicago O'Hare Intl Airport and Kentucky is 1,029 per week as of September 2025. The most frequent departure day is Mon, with 20% 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 September 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.

$40 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

Direct

Cheap round-trip flights

12:53 pm - 2:29 pmORD-BNA

1h 36mnonstop

9:59 pm - 11:44 pmBNA-ORD

1h 45mnonstop

$74Frontier

Find Deal

Thu, Oct 16 - Mon, Oct 20

7:20 pm - 9:04 pmORD-BNA

1h 44mnonstop

9:59 pm - 11:44 pmBNA-ORD

1h 45mnonstop

$78Frontier

Find Deal

Fri, Oct 17 - Mon, Oct 20

4:01 pm - 5:41 pmORD-BNA

1h 40mnonstop

6:46 pm - 8:31 pmBNA-ORD

1h 45mnonstop

$85Spirit Airlines

Find Deal

Thu, Nov 13 - Sun, Nov 16

9:10 pm - 10:59 pmORD-BNA

1h 49mnonstop

4:48 pm - 6:55 pmBNA-ORD

2h 07mnonstop

$97United Airlines

Find Deal

Mon, Oct 20 - Mon, Oct 27

7:50 pm - 10:30 pmORD-SDF

1h 40mnonstop

7:20 pm - 8:09 pmSDF-ORD

1h 49mnonstop

$97United Airlines

Find Deal

Wed, Oct 15 - Wed, Oct 22

1:26 pm - 3:10 pmORD-BNA

1h 44mnonstop

9:02 pm - 10:49 pmBNA-ORD

1h 47mnonstop

$99Spirit Airlines

Find Deal

Thu, Oct 9 - Sun, Oct 12

7:00 am - 8:34 amORD-BNA

1h 34mnonstop

5:25 am - 7:15 amBNA-ORD

1h 50mnonstop

$118American Airlines

Find Deal

Sat, Nov 1 - Mon, Nov 3

5:30 pm - 7:00 pmORD-OWB

1h 30mnonstop

3:00 pm - 4:35 pmOWB-ORD

1h 35mnonstop

$125Contour

Find Deal

Sun, Oct 5 - Wed, Oct 8

8:28 pm - 11:03 pmORD-SDF

1h 35mnonstop

6:04 am - 6:44 amSDF-ORD

1h 40mnonstop

$138American Airlines

Find Deal

Wed, Oct 29 - Tue, Dec 2

10:55 am - 12:25 pmORD-OWB

1h 30mnonstop

8:40 am - 10:15 amOWB-ORD

1h 35mnonstop

$138Contour

Find Deal

Fri, Oct 24 - Mon, Oct 27

Southwest flights from Chicago O'Hare Intl Airport to Kentucky

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

Southwest

Oct 22

ORD3:10 pmChicago O'Hare Intl

1h 35m

BNA4:45 pmNashville Intl

Oct 29

BNA1:55 pmNashville Intl

9h 10m

2 stops

ORD11:05 pmChicago O'Hare Intl

$112

Find similar

Southwest

Oct 23

ORD1:50 pmChicago O'Hare Intl

8h 25m

1 stop

BNA10:15 pmNashville Intl

Oct 28

BNA10:55 amNashville Intl

1h 50m

ORD12:45 pmChicago O'Hare Intl

$113

Find similar

Southwest

Oct 20

ORD1:50 pmChicago O'Hare Intl

5h 35m

1 stop

BNA7:25 pmNashville Intl

Oct 22

BNA4:35 pmNashville Intl

6h 30m

1 stop

ORD11:05 pmChicago O'Hare Intl

$117

Find similar

Frontier flights from Chicago O'Hare Intl Airport to Kentucky

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

Frontier

Oct 16

ORD12:53 pmChicago O'Hare Intl

1h 36m

BNA2:29 pmNashville Intl

Oct 20

BNA9:59 pmNashville Intl

1h 45m

ORD11:44 pmChicago O'Hare Intl

$74

Find similar

Frontier

Oct 3

ORD12:31 pmChicago O'Hare Intl

1h 43m

BNA2:14 pmNashville Intl

Oct 6

BNA3:11 pmNashville Intl

2h 05m

ORD5:16 pmChicago O'Hare Intl

$76

Find similar

Frontier

Oct 17

ORD7:20 pmChicago O'Hare Intl

1h 44m

BNA9:04 pmNashville Intl

Oct 20

BNA9:59 pmNashville Intl

1h 45m

ORD11:44 pmChicago O'Hare Intl

$78

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

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/16

12:53 pm-2:29 pm

Nonstop1h 36m

Nashville Intl

Mon 10/20

9:59 pm-11:44 pm

Nonstop1h 45m

$74

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 10/17

7:20 pm-9:04 pm

Nonstop1h 44m

Nashville Intl

Mon 10/20

9:59 pm-11:44 pm

Nonstop1h 45m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 11/13

4:01 pm-5:41 pm

Nonstop1h 40m

Nashville Intl

Sun 11/16

6:46 pm-8:31 pm

Nonstop1h 45m

$85

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 10/20

9:10 pm-10:59 pm

Nonstop1h 49m

Nashville Intl

Mon 10/27

4:48 pm-6:55 pm

Nonstop2h 07m

$97

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 10/15

7:50 pm-10:30 pm

Nonstop1h 40m

Louisville Intl

Wed 10/22

7:20 pm-8:09 pm

Nonstop1h 49m

$97

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/9

1:26 pm-3:10 pm

Nonstop1h 44m

Nashville Intl

Sun 10/12

9:02 pm-10:49 pm

Nonstop1h 47m

$99

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 11/1

7:00 am-8:34 am

Nonstop1h 34m

Nashville Intl

Mon 11/3

5:25 am-7:15 am

Nonstop1h 50m

$118

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sun 10/5

5:30 pm-7:00 pm

Nonstop1h 30m

Owensboro Daviess County

Wed 10/8

3:00 pm-4:35 pm

Nonstop1h 35m

$125

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 10/29

8:28 pm-11:03 pm

Nonstop1h 35m

Louisville Intl

Tue 12/2

6:04 am-6:44 am

Nonstop1h 40m

$138

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 10/24

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 10/27

8:40 am-10:15 am

Nonstop1h 35m

$138

Flights are sorted by cheapest round-trip flights first.

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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 $242.

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 $534. 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 afternoon. momondo users have found flights departing from Chicago O'Hare Intl Airport to Kentucky in the afternoon for as low as $278. 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 morning when prices are around $316.

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 $329 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 $186 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	$130
Fastest flight time	1h 14m
Direct flights	Every day
Airports in Kentucky	4 airports

The best one-way flight to Kentucky from Chicago O'Hare Intl Airport in the past 72 hours is $130. The best round-trip flight deal from Chicago O'Hare Intl Airport to Kentucky found on momondo in the last 72 hours is $142.

The fastest flight from Chicago O'Hare Intl Airport to Kentucky takes 1h 14m

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

There are 4 airports near Kentucky: Evansville Dress Regional (EVV), Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG), Lexington Blue Grass (LEX)

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 September 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 21.56% of all bookings. The subsequent popular models are Canadair (Bombardier) Regional Jet CRJ-550 at 20.94%, Canadair (Bombardier) Regional Jet 700 at 11.77%, and Canadair (Bombardier) Regional Jet at 11.56%.

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 $106	Free Cancellation	Rating 7.2 36 reviews	Search Contour flights
American Airlines	PriceFrom $121	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $137	Free Cancellation	Rating 7.4 8,928 reviews	Search United 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

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.

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Popular cities in Kentucky

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Chicago O'Hare Intl Airport flight routes

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Cheap flights from Chicago O'Hare Intl Airport to Kentucky from $40

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Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

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

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Southwest flights from Chicago O'Hare Intl Airport to Kentucky

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

Frontier flights from Chicago O'Hare Intl Airport to Kentucky

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

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.

See travel insights to Kentucky from

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

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 $242.

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, Frontier, and Southwest 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 147 per day as of September 2025. The most frequent departure time is 8:00PM, with 41% 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 1,029 per week as of September 2025. The most frequent departure day is Mon, with 20% 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