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$61+ Cheap flights from O'Hare Intl (ORD) to Kentucky

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SDF
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Kentucky

Cheapest flights from O'Hare Intl to Kentucky
Explore the most affordable flight options available from O'Hare Intl to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Mytrip deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:30 pm
ORD
-
OWB
Nonstop1h 30m
Contour
Sun 2/158:40 am
OWB
-
ORD
Nonstop1h 35m
Contour
Deal found 1/27$104
This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/149:40 am
ORD
-
OWB
Nonstop1h 30m
Contour
Mon 2/168:40 am
OWB
-
ORD
Nonstop1h 35m
Contour
Deal found 1/28$105
This Booking.com deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2911:20 am
ORD
-
OWB
Nonstop1h 35m
Contour
Sun 5/39:00 am
OWB
-
ORD
Nonstop1h 40m
Contour
Deal found 1/26$111
This Booking.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/319:40 am
ORD
-
OWB
Nonstop1h 30m
Contour
Sun 2/13:10 pm
OWB
-
ORD
Nonstop1h 35m
Contour
Deal found 1/27$117
This Contour deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Contour is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:40 am
ORD
-
OWB
Nonstop1h 30m
Contour
Tue 2/241:55 pm
OWB
-
ORD
Nonstop1h 35m
Contour
Deal found 1/28$118
This Kiwi.com deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:05 am
ORD
-
CVG
1 stop17h 28m
Frontier
Mon 2/231:07 pm
CVG
-
ORD
1 stop22h 44m
Frontier
Deal found 1/28$138
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/195:05 am
ORD
-
CVG
1 stop11h 27m
Frontier
Mon 2/231:07 pm
CVG
-
ORD
1 stop22h 44m
Frontier
Deal found 1/29$145
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/186:02 pm
ORD
-
CVG
1 stop22h 30m
Frontier
Sun 2/221:07 pm
CVG
-
ORD
1 stop22h 44m
Frontier
Deal found 1/27$152
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/144:42 pm
ORD
-
CVG
1 stop5h 51m
Frontier
Mon 2/161:07 pm
CVG
-
ORD
1 stop28h 50m
Frontier
Deal found 1/27$154
This United Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2410:50 am
ORD
-
CVG
Nonstop1h 27m
United Airlines
Tue 3/34:15 pm
CVG
-
ORD
Nonstop1h 35m
United Airlines
Deal found 1/27$157
This KAYAK deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:01 pm
ORD
-
CVG
Nonstop1h 27m
United Airlines
Thu 2/197:00 am
CVG
-
ORD
Nonstop1h 32m
United Airlines
Deal found 1/27$162
This Kiwi.com deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:02 pm
ORD
-
CVG
1 stop22h 30m
Frontier
Wed 3/43:20 pm
CVG
-
ORD
1 stop20h 26m
Frontier
Deal found 1/27$163

Find flight deals from O'Hare Intl to Kentucky

Keep the following information in mind while searching for O'Hare Intl to Kentucky flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$104
(Mytrip)

One-way from

$61
(Kiwi.com)

Popular in

June

Cheapest in

August

Average price

$319

Good round-trip deal

$108 or less

Good one-way deal

$55 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
Search Deals
From Chicago O'Hare Intl to Kentucky
Search Deals
One-way flight from Chicago O'Hare Intl to Kentucky
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago O'Hare Intl to Kentucky.
Search Deals
Price to beat on a one-way flight from Chicago O'Hare Intl to Kentucky.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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, Cheapflights users made 2,558,603 searches. Data last updated January 29, 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

O'Hare Intl

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Thu 2/12

10:55 am-12:25 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 2/16

3:10 pm-4:45 pm

Nonstop1h 35m

$104

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 2/11

5:30 pm-7:00 pm

Nonstop1h 30m

Owensboro Daviess County

Sun 2/15

8:40 am-10:15 am

Nonstop1h 35m

$104

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Fri 3/20

10:55 am-12:30 pm

Nonstop1h 35m

Owensboro Daviess County

Tue 3/24

1:50 pm-3:30 pm

Nonstop1h 40m

$105

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 3/21

9:40 am-11:15 am

Nonstop1h 35m

Owensboro Daviess County

Tue 3/24

1:50 pm-3:30 pm

Nonstop1h 40m

$105

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 2/14

9:40 am-11:10 am

Nonstop1h 30m

Owensboro Daviess County

Mon 2/16

8:40 am-10:15 am

Nonstop1h 35m

$105

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Wed 4/29

11:20 am-12:55 pm

Nonstop1h 35m

Owensboro Daviess County

Sun 5/3

9:00 am-10:40 am

Nonstop1h 40m

$111

ChicagoOwensboro

ORD - OWB

ORDOWB

Chicago O'Hare Intl

Sat 2/21

9:40 am-11:10 am

Nonstop1h 30m

Owensboro Daviess County

Tue 2/24

1:55 pm-3:30 pm

Nonstop1h 35m

$118

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/19

5:05 am-5:32 pm

1 stop11h 27m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:39 pm

1 stop10h 32m

$148

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 2/25

6:00 pm-8:18 pm

Nonstop1h 18m

Cincinnati Cinci./N. Kentucky

Wed 3/4

2:10 pm-2:45 pm

Nonstop1h 35m

$157

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 3/26

3:05 pm-5:25 pm

Nonstop1h 20m

Cincinnati Cinci./N. Kentucky

Tue 3/31

6:51 pm-7:27 pm

Nonstop1h 36m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 60 results
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Best time to book a flight from O'Hare Intl to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Kentucky

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Kentucky?

Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kentucky (average of $98). Flying from Chicago O'Hare Intl Airport to Kentucky in November is currently the most expensive (average of $189). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to KY?

Find hourly flight availability from O'Hare Intl to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.

It’s optimal to fly from Chicago O'Hare Intl Airport to Kentucky in the morning. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Kentucky?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Kentucky. Price data was last updated on January 24, 2026.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Kentucky flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago O'Hare Intl Airport to Kentucky

Explore weekly flight availability from O'Hare Intl to Kentucky. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 29, 2026.

The most flights from ORD to USKY are scheduled on a Monday (30 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kentucky. Reviews last updated January 29, 2026.
See what other customers who have flown with Contour, United Airlines, and American Airlines from Chicago O'Hare Intl Airport to Kentucky have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Contour
7.6
Good
42 reviews

Food

6.8

Boarding

7.6

Comfort

7.3

Overall

7.6

Crew

7.9

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
Contour
7.6
Good
42 reviews
Contour
7.6
Good
42 reviews

Food

6.8

Boarding

7.6

Comfort

7.3

Overall

7.6

Crew

7.9

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
United Airlines
7.4
Good
9,214 reviews
Contour
7.6
Good
42 reviews

Food

6.8

Boarding

7.6

Comfort

7.3

Overall

7.6

Crew

7.9

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo
American Airlines
7.2
Good
11,206 reviews
Contour
7.6
Good
42 reviews

Food

6.8

Boarding

7.6

Comfort

7.3

Overall

7.6

Crew

7.9

Entertainment

6.1

Reviews

1 / 2
10.0
Excellent

Anonymous,Oct 2025

CLT - PAH

The steward on my flight from Charlotte to Paducah was the kindest person I’ve ever met. He made everyone feel comfortable, and even laugh a little. Not to mention his hair was top tier. He deserves a raise. Xoxo

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago O'Hare Intl Airport to Kentucky?

    For as low as $157, Contour can have you in Kentucky from Chicago O'Hare Intl Airport in 1h 18m. Airlines will cover a distance of 265 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago O'Hare Intl Airport to Kentucky?

    Most travelers choose Chicago O'Hare Intl - Nashville Intl, Chicago O'Hare Intl - Cincinnati Cinci./N. Kentucky or Chicago O'Hare Intl - Knoxville McGhee Tyson when deciding on the best route from Chicago O'Hare Intl Airport to Kentucky.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Kentucky?

    Before booking your flight to Kentucky from Chicago O'Hare Intl Airport, check out the most reliable airlines to get you to your destination on time: Lufthansa (77%), SkyWest Airlines (76%), Japan Airlines( 75%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Kentucky?

    Looking at all options, your cheapest flight can be booked for $86. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $138 on average, our data indicates $804 when flying from Chicago O'Hare Intl Airport to Kentucky.

  • Can I find deals for flights from O'Hare Intl to Kentucky that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Kentucky.

  • Can I find deals for business class flights from O'Hare Intl to Kentucky?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Kentucky by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Kentucky?

    Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Kentucky (average of $98). Flying from Chicago O'Hare Intl Airport to Kentucky in November is currently the most expensive (average of $189). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for O'Hare Intl to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Orlando flights
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Midway to Los Angeles flights
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O'Hare Intl to Dulles Intl flights
O'Hare Intl to Boston flights
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O'Hare Intl to Honolulu flights
Midway to John F Kennedy Intl flights
Midway to Tampa flights
Midway to Hobby flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Love Field flights
O'Hare Intl to Key West flights
O'Hare Intl to Palm Springs flights
Midway to Newark flights
Midway to Fort Myers flights
O'Hare Intl to Charleston flights
Midway to Denver flights

Top 3 airlines flying from O'Hare Intl to Kentucky

Discover the top 3 airlines that operate flights from O'Hare Intl to Kentucky. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$108Average$148FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$127Average$323FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$287FlexibilityNo cancel feeOn-time71%

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