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 56 per day as of October 2026. The most frequent departure time is 9:00PM, with 45% of daily flights leaving in the afternoon.

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 394 per week as of October 2026. The most frequent departure day is Wed, with 16% of weekly flights leaving 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 O'Hare Intl Airport according to our data. United Airlines is the first choice among our users, with 55% 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.

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

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

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 3 operators available for flights from Chicago O'Hare Intl Airport to Kentucky as of October 2026.

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.

$98 Cheap Flights from Chicago O'Hare Intl Airport to Kentucky in 2026/27

Discover deals from 900+ travel sites with momondo.

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

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

11:59 am - 1:28 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 29mnonstop

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Wed, Jan 6 - Mon, Jan 18

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Thu, Oct 22 - Mon, Oct 26

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Fri, Oct 30 - Fri, Nov 6

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Tue, Nov 3 - Tue, Nov 10

7:08 am - 9:38 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 30mnonstop

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

$197American Airlines

Thu, Nov 5 - Tue, Nov 10

10:00 am - 12:40 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 40mnonstop

10:13 am - 11:00 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 47mnonstop

$197American Airlines

Thu, Dec 3 - Sat, Dec 5

2:42 pm - 5:13 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

$197American Airlines

Thu, Nov 5 - Mon, Nov 9

6:49 am - 2:16 pmORD Chicago O'Hare Intl-SDF Louisville Intl

6h 27m1 stop Atlanta Hartsfield-Jackson

10:59 am - 1:56 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

3h 57m1 stop Detroit Metropolitan Wayne County

$217Delta

Thu, Dec 3 - Sat, Dec 5

8:29 am - 1:53 pmORD Chicago O'Hare Intl-SDF Louisville Intl

4h 24m1 stop Detroit Metropolitan Wayne County

1:59 pm - 8:38 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

7h 39m1 stop Atlanta Hartsfield-Jackson

$227Delta

Thu, Oct 29 - Mon, Nov 2

6:16 pm - 12:09 amORD Chicago O'Hare Intl-SDF Louisville Intl

4h 53m1 stop Atlanta Hartsfield-Jackson

1:04 pm - 7:09 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

7h 05m1 stop Atlanta Hartsfield-Jackson

$227Delta

Mon, Dec 14 - Wed, Dec 16

Cheap last minute flights

Enter your travel dates to find the best prices.

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

$294United Airlines

Tue, Oct 13 - Sun, Oct 18

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

$334United Airlines

Thu, Oct 15 - Sun, Oct 18

5:50 pm - 8:28 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 38mnonstop

8:50 am - 9:35 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

$372United Airlines

Wed, Oct 14 - Thu, Oct 22

1:17 pm - 9:52 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

7h 35m1 stop Charlotte Douglas

11:14 am - 11:59 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

$382American Airlines

Wed, Oct 14 - Thu, Oct 22

9:35 pm - 12:09 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 34mnonstop

11:14 am - 11:59 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

$389American Airlines

Thu, Oct 15 - Sat, Oct 17

1:17 pm - 7:31 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

5h 14m1 stop Charlotte Douglas

8:03 pm - 12:08 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

5h 05m1 stop Charlotte Douglas

$392American Airlines

Wed, Oct 14 - Thu, Oct 22

5:50 pm - 8:28 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 38mnonstop

9:00 am - 9:40 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 40mnonstop

$396United Airlines

Sun, Oct 11 - Thu, Nov 12

9:51 am - 5:14 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

6h 23m1 stop Atlanta Hartsfield-Jackson

7:45 am - 10:29 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

3h 44m1 stop Detroit Metropolitan Wayne County

$409Delta

Thu, Oct 15 - Sun, Oct 18

8:05 am - 2:49 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

5h 44m1 stop Atlanta Hartsfield-Jackson

1:04 pm - 4:58 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

4h 54m1 stop Atlanta Hartsfield-Jackson

$409Delta

Thu, Oct 15 - Sat, Oct 17

8:05 am - 2:49 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

5h 44m1 stop Atlanta Hartsfield-Jackson

7:45 am - 12:59 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

6h 14m1 stop Detroit Metropolitan Wayne County

$409Delta

Thu, Oct 15 - Sun, Oct 18

Cheap direct flights

Enter your travel dates to find the best prices.

11:59 am - 1:28 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 29mnonstop

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Wed, Jan 6 - Mon, Jan 18

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Thu, Oct 22 - Mon, Oct 26

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Fri, Oct 30 - Fri, Nov 6

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Tue, Nov 3 - Tue, Nov 10

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

$194United Airlines

Thu, Oct 29 - Sun, Nov 1

9:30 pm - 11:05 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 35mnonstop

2:25 pm - 4:15 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

$196United Airlines

Thu, Oct 29 - Thu, Nov 5

7:08 am - 9:38 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 30mnonstop

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

$197American Airlines

Thu, Nov 5 - Tue, Nov 10

10:00 am - 12:40 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 40mnonstop

10:13 am - 11:00 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 47mnonstop

$197American Airlines

Thu, Dec 3 - Sat, Dec 5

4:00 pm - 6:32 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 32mnonstop

9:17 am - 10:00 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 43mnonstop

$197United Airlines

Fri, Nov 13 - Tue, Nov 17

2:42 pm - 5:13 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

$197American Airlines

Thu, Nov 5 - Mon, Nov 9

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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

Nov 5

ORD7:08 amChicago O'Hare Intl

1h 30m

SDF9:38 amLouisville Intl

Nov 10

SDF6:27 amLouisville Intl

1h 48m

ORD7:15 amChicago O'Hare Intl

$197

American Airlines

Oct 29

ORD9:39 amChicago O'Hare Intl

1h 31m

SDF12:10 pmLouisville Intl

Nov 2

SDF10:13 amLouisville Intl

1h 47m

ORD11:00 amChicago O'Hare Intl

$208

American Airlines

Nov 21

ORD6:54 amChicago O'Hare Intl

1h 34m

SDF9:28 amLouisville Intl

Nov 22

SDF6:31 pmLouisville Intl

1h 59m

ORD7:30 pmChicago O'Hare Intl

$231

Delta flights from Chicago O'Hare Intl Airport to Kentucky

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

Delta

Dec 3

ORD6:49 amChicago O'Hare Intl

6h 27m

1 stop

SDF2:16 pmLouisville Intl

Dec 5

SDF10:59 amLouisville Intl

3h 57m

1 stop

ORD1:56 pmChicago O'Hare Intl

$217

Delta

Oct 29

ORD8:29 amChicago O'Hare Intl

4h 24m

1 stop

SDF1:53 pmLouisville Intl

Nov 2

SDF1:59 pmLouisville Intl

7h 39m

1 stop

ORD8:38 pmChicago O'Hare Intl

$227

Delta

Oct 27

ORD12:30 pmChicago O'Hare Intl

4h 29m

1 stop

SDF5:59 pmLouisville Intl

Oct 30

SDF1:59 pmLouisville Intl

7h 39m

1 stop

ORD8:38 pmChicago O'Hare Intl

$239

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

Cheapest round-trip

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Wed 1/6

11:59 am-1:28 pm

Nonstop1h 29m

Paducah Barkley Regional

Mon 1/18

5:00 am-6:29 am

Nonstop1h 29m

$194

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Thu 10/22

12:02 pm-1:32 pm

Nonstop1h 30m

Paducah Barkley Regional

Mon 10/26

5:30 am-6:59 am

Nonstop1h 29m

$194

Quickest round-trip

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Fri 10/30

12:14 pm-1:41 pm

Nonstop1h 27m

Paducah Barkley Regional

Fri 11/6

5:30 am-6:59 am

Nonstop1h 29m

$194

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Tue 11/3

12:14 pm-1:41 pm

Nonstop1h 27m

Paducah Barkley Regional

Tue 11/10

5:30 am-6:59 am

Nonstop1h 29m

$194

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Thu 11/5

7:08 am-9:38 am

Nonstop1h 30m

Louisville Intl

Tue 11/10

6:27 am-7:15 am

Nonstop1h 48m

$197

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Thu 12/3

10:00 am-12:40 pm

Nonstop1h 40m

Louisville Intl

Sat 12/5

10:13 am-11:00 am

Nonstop1h 47m

$197

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Thu 11/5

2:42 pm-5:13 pm

Nonstop1h 31m

Louisville Intl

Mon 11/9

6:27 am-7:15 am

Nonstop1h 48m

$197

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Thu 12/3

6:49 am-2:16 pm

1 stop6h 27m

Louisville Intl

Sat 12/5

10:59 am-1:56 pm

1 stop3h 57m

$217

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Thu 10/29

8:29 am-1:53 pm

1 stop4h 24m

Louisville Intl

Mon 11/2

1:59 pm-8:38 pm

1 stop7h 39m

$227

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Mon 12/14

6:16 pm-12:09 am

1 stop4h 53m

Louisville Intl

Wed 12/16

1:04 pm-7:09 pm

1 stop7h 05m

$227

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 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 December, then November is your next best option. Flight prices from Chicago O'Hare Intl Airport to Kentucky during November average around $288.

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

Our data shows that Thursday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $326. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $501. 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 O'Hare Intl Airport to Kentucky in the morning for as low as $373. 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 $494.

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 from Chicago O'Hare Intl Airport 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 $406 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 $222 on momondo.

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

There are 4 cabin classes available to choose from on Chicago O'Hare Intl Airport 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	$98
Fastest flight time	1h 20m
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 $98. The best round-trip flight deal from Chicago O'Hare Intl Airport to Kentucky found on momondo in the last 72 hours is $194.

The fastest flight from Chicago O'Hare Intl Airport to Kentucky takes 1h 20m

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 Louisville Intl (SDF), Paducah Barkley Regional (PAH), Owensboro Daviess County (OWB), Lexington Blue Grass (LEX).

Search flight deals

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Kentucky

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 3 operators available for flights from Chicago O'Hare Intl Airport to Kentucky as of October 2026.
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 Canadair (Bombardier) Regional Jet CRJ-550, representing 24.33% of all bookings. The subsequent popular models are Embraer 175 (Enhanced Winglets) at 23.08%, Canadair (Bombardier) Regional Jet 700 at 14.85%, and Embraer 175 at 14.37%.

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 $89	Free Cancellation	Rating 7.5 43 reviews	Search Contour flights
United Airlines	PriceFrom $143	Free Cancellation	Rating 7.4 10,319 reviews	Search United Airlines flights
American Airlines	PriceFrom $189	Free Cancellation	Rating 7.0 12,145 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.