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Cheap flights from Chicago O'Hare Intl Airport to Kentucky from $51

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 O'Hare Intl Airport to Kentucky departing on 2/25. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Kentucky

Cheap round-trip flights

Enter your travel dates to find the best prices.
Contour Logo
10:55 am - 12:30 pm
ORD
-
OWB
1h 35mnonstop
Contour Logo
8:35 am - 10:15 am
OWB
-
ORD
1h 40mnonstop
$101Contour
Fri, Mar 6 - Mon, Mar 9
Contour Logo
9:40 am - 11:10 am
ORD
-
OWB
1h 30mnonstop
Contour Logo
1:55 pm - 3:30 pm
OWB
-
ORD
1h 35mnonstop
$102Contour
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
7:00 am - 9:21 am
ORD
-
CVG
1h 21mnonstop
American Airlines Logo
5:00 am - 5:31 am
CVG
-
ORD
1h 31mnonstop
$157American Airlines
Fri, Mar 27 - Sun, Mar 29
Delta Logo
5:25 am - 12:17 pm
ORD
-
TRI
5h 52m
1 stop
Delta Logo
7:17 pm - 11:54 pm
TRI
-
ORD
5h 37m
1 stop
$159Delta
Wed, Mar 4 - Mon, Mar 9
Frontier Logo
1:27 pm - 9:54 pm
ORD
-
CVG
7h 27m
1 stop
Frontier Logo
1:05 pm - 12:52 am
CVG
-
ORD
12h 47m
1 stop
$160Frontier
Fri, Apr 24 - Sun, Apr 26
Frontier Logo
8:24 pm - 1:05 pm
ORD
-
CVG
15h 41m
1 stop
Frontier Logo
4:26 pm - 9:15 am
CVG
-
ORD
17h 49m
1 stop
$161Frontier
Thu, May 7 - Sat, May 9
United Airlines Logo
6:05 pm - 8:29 pm
ORD
-
CVG
1h 24mnonstop
United Airlines Logo
6:10 pm - 6:51 pm
CVG
-
ORD
1h 41mnonstop
$164United Airlines
Tue, Apr 7 - Sat, Apr 11
Delta Logo
9:52 am - 5:03 pm
ORD
-
CVG
6h 11m
1 stop
Delta Logo
6:05 am - 10:25 am
CVG
-
ORD
5h 20m
1 stop
$167Delta
Tue, Mar 3 - Sat, Mar 7
American Airlines Logo
2:01 pm - 4:21 pm
ORD
-
CVG
1h 20mnonstop
American Airlines Logo
6:26 pm - 7:02 pm
CVG
-
ORD
1h 36mnonstop
$171American Airlines
Thu, Mar 5 - Mon, Mar 9
United Airlines Logo
7:40 pm - 10:13 pm
ORD
-
SDF
1h 33mnonstop
United Airlines Logo
9:00 am - 9:44 am
SDF
-
ORD
1h 44mnonstop
$177United Airlines
Tue, Mar 3 - Wed, Mar 4

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
Mar 7
ORD12:44 pmChicago O'Hare Intl
17h 41m
2 stops
BNA6:25 amNashville Intl
Mar 9
BNA8:52 pmNashville Intl
14h 30m
1 stop
ORD11:22 amChicago O'Hare Intl
$200
Spirit Airlines
Mar 7
ORD8:16 pmChicago O'Hare Intl
10h 09m
1 stop
BNA6:25 amNashville Intl
Mar 9
BNA8:52 pmNashville Intl
20h 54m
3 stops
ORD5:46 pmChicago O'Hare Intl
$212
Spirit Airlines
Feb 23
ORD12:44 pmChicago O'Hare Intl
7h 13m
1 stop
BNA7:57 pmNashville Intl
Feb 24
BNA8:30 amNashville Intl
10h 41m
1 stop
ORD7:11 pmChicago O'Hare Intl
$213

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
Mar 11
ORD2:40 pmChicago O'Hare Intl
4h 25m
1 stop
TYS8:05 pmKnoxville McGhee Tyson
Mar 17
TYS12:30 pmKnoxville McGhee Tyson
7h 05m
1 stop
ORD6:35 pmChicago O'Hare Intl
$209
Southwest
Mar 16
ORD2:40 pmChicago O'Hare Intl
1h 45m
BNA4:25 pmNashville Intl
Mar 18
BNA11:00 amNashville Intl
1h 50m
ORD12:50 pmChicago O'Hare Intl
$217
Southwest
Mar 7
ORD2:40 pmChicago O'Hare Intl
1h 45m
BNA4:25 pmNashville Intl
Mar 9
BNA3:45 pmNashville Intl
6h 10m
1 stop
ORD9:55 pmChicago O'Hare Intl
$226

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to Kentucky that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 11, 2026.
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

Fri 3/6

10:55 am-12:30 pm

Nonstop1h 35m

Owensboro Daviess County

Mon 3/9

8:35 am-10:15 am

Nonstop1h 40m

$101

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Tue 2/24

9:40 am-11:10 am

Nonstop1h 30m

Owensboro Daviess County

Sat 2/28

1:55 pm-3:30 pm

Nonstop1h 35m

$102

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Fri 3/27

7:00 am-9:21 am

Nonstop1h 21m

Cincinnati Cinci./N. Kentucky

Sun 3/29

5:00 am-5:31 am

Nonstop1h 31m

$157

ChicagoBlountville

ORD - TRI

ORDTRI

Chicago O'Hare Intl

Wed 3/4

5:25 am-12:17 pm

1 stop5h 52m

Blountville Tri Cities TN/VA

Mon 3/9

7:17 pm-11:54 pm

1 stop5h 37m

$159

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Fri 4/24

1:27 pm-9:54 pm

1 stop7h 27m

Cincinnati Cinci./N. Kentucky

Sun 4/26

1:05 pm-12:52 am

1 stop12h 47m

$160

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 5/7

8:24 pm-1:05 pm

1 stop15h 41m

Cincinnati Cinci./N. Kentucky

Sat 5/9

4:26 pm-9:15 am

1 stop17h 49m

$161

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 4/7

6:05 pm-8:29 pm

Nonstop1h 24m

Cincinnati Cinci./N. Kentucky

Sat 4/11

6:10 pm-6:51 pm

Nonstop1h 41m

$164

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 3/3

9:52 am-5:03 pm

1 stop6h 11m

Cincinnati Cinci./N. Kentucky

Sat 3/7

6:05 am-10:25 am

1 stop5h 20m

$167

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 3/5

2:01 pm-4:21 pm

Nonstop1h 20m

Cincinnati Cinci./N. Kentucky

Mon 3/9

6:26 pm-7:02 pm

Nonstop1h 36m

$171

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 3/3

7:40 pm-10:13 pm

Nonstop1h 33m

Louisville Intl

Wed 3/4

9:00 am-9:44 am

Nonstop1h 44m

$177

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 December is your next best option. Flight prices from Chicago O'Hare Intl Airport to Kentucky during December average around $240.

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 Sunday because tickets tend to average around $449. 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 $295. 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 $330.

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 $321 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 $124 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

$53

Fastest flight time

1h 16m

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 $53. The best round-trip flight deal from Chicago O'Hare Intl Airport to Kentucky found on momondo in the last 72 hours is $108.
The fastest flight from Chicago O'Hare Intl Airport to Kentucky takes 1h 16m
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), 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?

  • 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?

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
ContourPriceFrom $108Free CancellationRating
7.6
42 reviews
Search Contour flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
9,274 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
11,266 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.

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