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O'Hare Intl

$72+ Cheap flights from Kentucky to O'Hare Intl (ORD)

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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Aug 29 — Sep 51
Sat 8/29
Sat 9/5
1 adult, Economy
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Cheap flight deals from Kentucky to O'Hare Intl

Cheapest flights from Kentucky to O'Hare Intl
Explore the most affordable flight options available from Kentucky to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2026.

This American Airlines deal was found by Cheapflights users on 7/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:34 am
CVG
-
ORD
Nonstop1h 43m
American Airlines
Fri 9/116:30 pm
ORD
-
CVG
Nonstop1h 34m
American Airlines
Deal found 7/29$167
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1910:53 am
CVG
-
ORD
1 stop6h 24m
Delta
Sat 8/226:59 am
ORD
-
CVG
1 stop5h 43m
Delta
Deal found 7/28$177
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2911:50 am
CVG
-
ORD
1 stop5h 27m
Delta
Sun 9/66:59 am
ORD
-
CVG
1 stop5h 43m
Delta
Deal found 7/27$182
This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Sun 8/2312:26 pm
CVG
-
ORD
1 stop20h 27m
Frontier
Tue 8/251:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/29$183
This Delta deal was found by Cheapflights users on 7/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:27 am
CVG
-
ORD
1 stop5h 15m
Delta
Mon 8/175:20 pm
ORD
-
CVG
1 stop4h 20m
Delta
Deal found 7/25$187
This Kiwi.com deal was found by Cheapflights users on 7/29. 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 10/2912:48 pm
CVG
-
ORD
1 stop7h 56m
Frontier
Fri 10/302:03 pm
ORD
-
CVG
1 stop20h 40m
Frontier
Deal found 7/29$188
This Kiwi.com deal was found by Cheapflights users on 7/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/612:43 pm
CVG
-
ORD
1 stop6h 40m
Frontier
Wed 10/77:28 pm
ORD
-
CVG
1 stop15h 15m
Frontier
Deal found 7/26$190
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
Mon 8/2412:26 pm
CVG
-
ORD
1 stop8h 33m
Frontier
Tue 8/251:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/25$192
This Kiwi.com deal was found by Cheapflights users on 7/28. 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.
Fri 8/2812:26 pm
CVG
-
ORD
1 stop8h 33m
Frontier
Sat 8/291:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/28$193
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/135:00 am
PAH
-
ORD
Nonstop1h 28m
United Airlines
Mon 8/1711:40 am
ORD
-
PAH
Nonstop1h 30m
United Airlines
Deal found 7/29$194
This United Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 8/2712:29 pm
CVG
-
ORD
Nonstop1h 34m
United Airlines
Sun 8/309:25 pm
ORD
-
CVG
Nonstop1h 28m
United Airlines
Deal found 7/27$196
This Kiwi.com deal was found by Cheapflights users on 7/25. 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 8/2912:26 pm
CVG
-
ORD
1 stop8h 42m
Frontier
Sat 9/51:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/25$197

Find flight deals from Kentucky to O'Hare Intl

Keep the following information in mind while searching for Kentucky to O'Hare Intl flight deals. Data was last updated July 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$167
(American Airlines)

One-way from

$72
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$337

Good round-trip deal

$163 or less

Good one-way deal

$263 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Chicago O'Hare Intl
Search Deals
One-way flight from Kentucky to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago O'Hare Intl.
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago O'Hare Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to O'Hare Intl 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 July 30, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 8/29

8:14 am-10:42 am

1 stop3h 28m

Chicago O'Hare Intl

Mon 8/31

5:20 pm-10:40 pm

1 stop4h 20m

$187
Quickest round-trip

PaducahChicago

PAH - ORD

PAHORD

Paducah Barkley Regional

Thu 8/13

5:00 am-6:28 am

Nonstop1h 28m

Chicago O'Hare Intl

Mon 8/17

11:40 am-1:10 pm

Nonstop1h 30m

$194

PaducahChicago

PAH - ORD

PAHORD

Paducah Barkley Regional

Thu 12/3

5:00 am-6:43 am

Nonstop1h 43m

Chicago O'Hare Intl

Sun 12/6

12:00 pm-1:30 pm

Nonstop1h 30m

$194

PaducahChicago

PAH - ORD

PAHORD

Paducah Barkley Regional

Sun 8/23

5:00 am-6:28 am

Nonstop1h 28m

Chicago O'Hare Intl

Sun 8/30

11:40 am-1:10 pm

Nonstop1h 30m

$194

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Tue 11/3

11:10 am-4:32 pm

1 stop6h 22m

Chicago O'Hare Intl

Thu 11/5

7:10 am-1:36 pm

1 stop5h 26m

$208

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 8/27

2:23 pm-6:29 pm

1 stop5h 06m

Chicago O'Hare Intl

Thu 9/3

8:48 am-3:28 pm

1 stop5h 40m

$216

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 8/20

2:23 pm-6:29 pm

1 stop5h 06m

Chicago O'Hare Intl

Mon 8/24

1:59 pm-7:54 pm

1 stop4h 55m

$216

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 11/5

6:24 am-8:35 am

Nonstop2h 11m

Chicago O'Hare Intl

Mon 11/9

8:50 pm-10:28 pm

Nonstop1h 38m

$217

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 8/24

9:00 am-9:41 am

Nonstop1h 41m

Chicago O'Hare Intl

Thu 8/27

10:35 am-1:11 pm

Nonstop1h 36m

$217

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 11/26

8:55 am-9:35 am

Nonstop1h 40m

Chicago O'Hare Intl

Mon 11/30

6:50 am-9:20 am

Nonstop1h 30m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Kentucky to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Kentucky 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 Kentucky to Chicago O'Hare Intl Airport

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

Currently, October is the cheapest month in which you can book a flight from Kentucky to Chicago O'Hare Intl Airport (average of $228). Flying from Kentucky to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $365). 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 KY to ORD?

Find hourly flight availability from Kentucky to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2026.

One of the essential ways to save on airfare from Kentucky to Chicago O'Hare Intl Airport is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 45% on airfare.

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

Explore weekly flight availability from Kentucky to O'Hare Intl. 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 July 30, 2026.

The most flights from USKY to ORD are scheduled on a Wednesday (38 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (18 on average).

How much does it cost to fly round-trip from Kentucky to Chicago O'Hare Intl Airport?

Airfare is below average for this route at the moment.
Kentucky to Chicago O'Hare Intl Airport flights typically cost between $227 and $349 in September.
The cheapest round-trip price found within the last 5 days was $217 on United Airlines (Sep 10-Sep 12).

How far ahead should I book a flight from Kentucky to Chicago O'Hare Intl Airport?

Booking 65 days in advance of your planned departure date is, on average, the best time to get cheap flights from Kentucky to Chicago O'Hare Intl Airport. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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

Use this chart to determine the cheapest time to fly round-trip from Kentucky to O'Hare Intl. Price data was last updated on July 25, 2026.

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

Related info for your journey

Find useful and relevant information for your journey from Kentucky to O'Hare Intl. 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 Kentucky to Chicago O'Hare Intl Airport?

    A quick flight from Kentucky to Chicago O'Hare Intl Airport can take about 1h 28m. Delta provides one of the quickest options available for as low as $194. There are 343 mi between Kentucky and Chicago O'Hare Intl Airport. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kentucky to Chicago O'Hare Intl Airport one-way?

    The cheapest airline one-way is Contour, with whom users have recently found tickets for as low as $44. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Kentucky to Chicago O'Hare Intl Airport for a low price.

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

    The most popular route from Kentucky to Chicago O'Hare Intl Airport is Nashville Intl - Chicago O'Hare Intl. You may also consider Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl or Knoxville McGhee Tyson - Chicago O'Hare Intl.

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

    The top 3 most reliable airlines when flying from Kentucky to Chicago O'Hare Intl Airport are Japan Airlines (91%), Qatar Airways (87%) and Republic Airways (86%).

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

    The cheapest flight price from Kentucky to Chicago O'Hare Intl Airport is $148. On average you can expect to pay $1,401. The most popular route, (Nashville Intl - Chicago O'Hare Intl), can usually be booked for $207.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kentucky to O'Hare Intl 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 Kentucky to Chicago O'Hare Intl Airport?

    Currently, October is the cheapest month in which you can book a flight from Kentucky to Chicago O'Hare Intl Airport (average of $228). Flying from Kentucky to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $365). 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Benton Harbor
Rosemont
Schaumburg
Naperville
Lake Geneva
Oak Brook
Delavan
Oakbrook Terrace
Gurnee
South Holland
Libertyville
Orland Park
Hoffman Estates
Beloit
Downers Grove
Rockford
Aurora
Racine
Great Lakes
Janesville

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Alternative routes for Kentucky to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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Baltimore to O'Hare Intl flights
Newark to Midway flights
Boston to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
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Philadelphia to O'Hare Intl flights
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Atlanta to O'Hare Intl flights
Hobby to O'Hare Intl flights
Orlando to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Tampa to O'Hare Intl flights
John F Kennedy Intl to Midway flights
George Bush Intcntl to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
LaGuardia to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Miami to O'Hare Intl flights
Dulles Intl to Midway flights
Los Angeles to Midway flights
Fort Lauderdale to O'Hare Intl flights
Hobby to Midway flights
Atlanta to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Philadelphia to Midway flights
Santa Ana to O'Hare Intl flights
Portland to O'Hare Intl flights
San Diego to O'Hare Intl flights
Minneapolis to Midway flights
George Bush Intcntl to Midway flights
Detroit to O'Hare Intl flights
Baltimore to Midway flights
Salt Lake City to O'Hare Intl flights
Reagan-National to Midway flights
Hartford to O'Hare Intl flights
Nashville to O'Hare Intl flights
Burbank to O'Hare Intl flights
White Plains to O'Hare Intl flights
Boston to Midway flights
Las Vegas to O'Hare Intl flights

Top 3 airlines flying from Kentucky to O'Hare Intl

Discover the top 3 airlines that operate flights from Kentucky to O'Hare Intl. 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 July 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$288FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$127Average$288FlexibilityNo cancel feeOn-time71%

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