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Kentucky

$64+ Cheap flights from Chicago (CHI) 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.
CHI — SDF
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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Cheap flight deals from Chicago to Kentucky

Keep the following information in mind while searching for Chicago to Kentucky flight deals. Data was last updated January 6, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$132
(Kiwi.com)

One-way from

$64
(Expedia)

Popular in

February

Cheapest in

August

Average price

$276

Good round-trip deal

$215 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Chicago (CHI)-Louisville Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Louisville Intl flights.
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From Chicago (CHI) to Kentucky
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One-way flight from Chicago (CHI) to Kentucky
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Highest demand for flights based on searches. 18% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Price to beat on a round-trip flight from Chicago (CHI) to Kentucky.
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Price to beat on a one-way flight from Chicago (CHI) to Kentucky.
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Find flight deals from Chicago to Kentucky

Cheapest flights from Chicago to Kentucky
Explore the most affordable flight options available from Chicago to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/6. 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 6/252:46 pmMDW - TYS
Nonstop1h 28mAllegiant Air
Sun 6/281:22 pmTYS - MDW
Nonstop1h 34mAllegiant Air
Deal found 1/6$132
This United Airlines deal was found by Cheapflights users on 1/6. 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 1/297:30 amORD - CVG
Nonstop1h 30mUnited Airlines
Thu 1/295:55 pmCVG - ORD
Nonstop1h 36mUnited Airlines
Deal found 1/6$143
This United Airlines deal was found by Cheapflights users on 1/6. 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 2/37:52 pmORD - SDF
Nonstop1h 38mUnited Airlines
Tue 2/108:29 amSDF - ORD
Nonstop1h 44mUnited Airlines
Deal found 1/6$143
This Frontier deal was found by Cheapflights users on 1/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:15 amORD - CVG
1 stop12h 10mFrontier
Mon 2/231:07 pmCVG - ORD
1 stop10h 32mFrontier
Deal found 1/5$144
This American Airlines deal was found by Cheapflights users on 1/6. 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.
Thu 1/2910:01 amORD - SDF
Nonstop1h 31mAmerican Airlines
Mon 2/28:07 amSDF - ORD
Nonstop1h 53mAmerican Airlines
Deal found 1/6$144
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/298:43 pmORD - CVG
1 stop16h 45mMultiple Airlines
Mon 2/25:39 pmCVG - ORD
1 stop29h 05mMultiple Airlines
Deal found 1/6$145
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 1/298:10 amORD - TYS
1 stop8h 43mMultiple Airlines
Sun 2/11:39 pmTYS - ORD
1 stop25h 28mMultiple Airlines
Deal found 1/4$149
This Kiwi.com deal was found by Cheapflights users on 1/3. 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 2/612:07 pmORD - CVG
1 stop7h 46mFrontier
Sun 2/85:47 pmCVG - ORD
1 stop7h 12mFrontier
Deal found 1/3$151
This Frontier deal was found by Cheapflights users on 1/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/193:00 pmMDW - CVG
1 stop8h 59mFrontier
Mon 2/231:07 pmCVG - MDW
1 stop10h 22mFrontier
Deal found 1/5$160
This Frontier deal was found by Cheapflights users on 1/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1911:41 amORD - CVG
1 stop12h 18mFrontier
Mon 2/231:07 pmCVG - ORD
1 stop10h 32mFrontier
Deal found 1/5$160
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/297:20 amORD - BNA
1 stop12h 23mSpirit Airlines
Mon 2/28:12 pmBNA - ORD
1 stop15h 10mSpirit Airlines
Deal found 1/5$160
This Frontier deal was found by Cheapflights users on 1/5. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:15 amMDW - CVG
1 stop9h 22mFrontier
Thu 2/265:20 amCVG - MDW
1 stop10h 06mFrontier
Deal found 1/5$161

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago 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 6, 2026.
Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.

Fly from

Chicago

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 1/29

7:30 am-10:00 am

Nonstop1h 30m

Cincinnati Cinci./N. Kentucky

Thu 1/29

5:55 pm-6:31 pm

Nonstop1h 36m

$143

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 2/17

9:05 am-11:30 am

Nonstop1h 25m

Louisville Intl

Tue 2/17

6:12 pm-7:00 pm

Nonstop1h 48m

$143

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 1/27

10:45 am-1:24 pm

Nonstop1h 39m

Louisville Intl

Wed 1/28

2:05 pm-2:49 pm

Nonstop1h 44m

$143

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Thu 3/5

10:43 am-1:17 pm

Nonstop1h 34m

Louisville Intl

Mon 3/9

1:58 pm-2:45 pm

Nonstop1h 47m

$143

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Fri 2/6

11:45 am-11:26 pm

1 stop10h 41m

Cincinnati Cinci./N. Kentucky

Mon 2/9

5:39 pm-3:52 pm

1 stop23h 13m

$145

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/19

12:44 pm-12:59 am

1 stop11h 15m

Cincinnati Cinci./N. Kentucky

Thu 2/26

6:54 pm-2:54 pm

1 stop21h 00m

$156

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

3:00 pm-12:59 am

1 stop8h 59m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:29 pm

1 stop10h 22m

$160

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/19

11:41 am-12:59 am

1 stop12h 18m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-10:39 pm

1 stop10h 32m

$160

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 1/29

6:00 am-11:15 am

1 stop4h 15m

Cincinnati Cinci./N. Kentucky

Mon 2/2

6:04 pm-10:22 pm

1 stop5h 18m

$163

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 2/17

6:00 am-11:08 am

1 stop4h 08m

Cincinnati Cinci./N. Kentucky

Wed 2/18

6:06 pm-10:31 pm

1 stop5h 25m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/4

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Chicago 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 to Kentucky

What is the cheapest month to book a flight from Chicago to Kentucky?

Currently, December is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $98). Flying from Chicago to Kentucky in June is currently the most expensive (average of $177). 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 CHI to KY?

Find hourly flight availability from Chicago 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 6, 2026.

When flying from Chicago to Kentucky, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 21% versus a flight at noon.

What is the cheapest day to fly from Chicago to Kentucky?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kentucky. Price data was last updated on January 3, 2026.

Travelers seeking maximum savings on their Chicago 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 to Kentucky

Explore weekly flight availability from Chicago 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 6, 2026.

The most flights from CHI to USKY are scheduled on a Monday (40 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Chicago to Kentucky?

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 6, 2026.
Read reviews from past customers who have flown Southwest, Contour, and United Airlines from Chicago to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Contour
7.6
Good
42 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,132 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,083 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago 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 to Kentucky?

    Departing from Chicago to Kentucky will take you 1h 25m. The distance from Chicago to Kentucky is about 287 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Chicago to Kentucky one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $38. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago to Kentucky for a low price.

  • What are the most popular routes from Chicago to Kentucky?

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

  • What are the most reliable airlines from Chicago to Kentucky?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Kentucky on time: Japan Airlines (77%), Lufthansa (73%), Republic Airways (73%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $102. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $143 on average, our data indicates $909 when flying from Chicago to Kentucky.

  • Can I find deals for flights from Chicago to Kentucky that include hotel bookings?

    Yes. In addition to deals on Chicago to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kentucky?

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

  • Can I find deals for business class flights from Chicago to Kentucky?

    Yes. Cheapflights offers flight deals from Chicago 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 to Kentucky?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $98). Flying from Chicago to Kentucky in June is currently the most expensive (average of $177). 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 Chicago to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Kentucky

Discover the top 4 airlines that operate flights from Chicago 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 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$124Average$404FlexibilityNo cancel feeOn-time63%
ContourCheapest$126Average$148FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$127Average$319FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$287FlexibilityNo cancel feeOn-time71%

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