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$39+ 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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$77
(Priceline)

One-way from

$39
(Southwest)

Popular in

February

Cheapest in

August

Average price

$255

Good round-trip deal

$129 or less

Good one-way deal

$137 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. 16% potential increase in price ($61 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 September 2025
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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 September 29, 2025.

This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/137:25 pmORD - BNA
Nonstop1h 44mFrontier
Thu 10/163:24 pmBNA - ORD
Nonstop1h 55mFrontier
Deal found 9/29$77
This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/134:44 pmORD - BNA
Nonstop1h 40mMultiple Airlines
Fri 10/179:59 pmBNA - ORD
Nonstop1h 45mMultiple Airlines
Deal found 9/28$78
This Kiwi.com deal was found by Cheapflights users on 9/27. 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.
Thu 10/307:06 pmORD - BNA
Nonstop1h 44mFrontier
Sun 11/28:49 pmBNA - ORD
Nonstop1h 48mFrontier
Deal found 9/27$80
This Trip.com deal was found by Cheapflights users on 9/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:26 pmORD - BNA
Nonstop1h 44mMultiple Airlines
Mon 10/209:59 pmBNA - ORD
Nonstop1h 45mMultiple Airlines
Deal found 9/27$81
This Priceline deal was found by Cheapflights users on 9/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:41 amORD - BNA
Nonstop1h 40mFrontier
Mon 12/152:16 pmBNA - ORD
Nonstop1h 54mFrontier
Deal found 9/29$82
This Cheapflightsfares deal was found by Cheapflights users on 9/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/612:43 pmORD - BNA
Nonstop1h 43mFrontier
Thu 10/93:24 pmBNA - ORD
Nonstop1h 55mFrontier
Deal found 9/28$83
This Trip.com deal was found by Cheapflights users on 9/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/51:26 pmORD - BNA
Nonstop1h 44mMultiple Airlines
Mon 10/63:11 pmBNA - ORD
Nonstop2h 05mMultiple Airlines
Deal found 9/27$84
This Priceline deal was found by Cheapflights users on 9/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/247:20 pmORD - BNA
Nonstop1h 44mMultiple Airlines
Mon 10/272:01 pmBNA - ORD
Nonstop1h 48mMultiple Airlines
Deal found 9/27$85
This Trip.com deal was found by Cheapflights users on 9/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:53 pmORD - BNA
Nonstop1h 36mFrontier
Fri 10/109:59 pmBNA - ORD
Nonstop1h 45mFrontier
Deal found 9/27$87
This Frontier deal was found by Cheapflights users on 9/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:01 pmORD - BNA
Nonstop1h 48mFrontier
Thu 11/138:49 pmBNA - ORD
Nonstop1h 48mFrontier
Deal found 9/29$88
This Priceline deal was found by Cheapflights users on 9/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/912:53 pmORD - BNA
Nonstop1h 36mMultiple Airlines
Fri 10/102:01 pmBNA - ORD
Nonstop1h 48mMultiple Airlines
Deal found 9/28$89
This Southwest deal was found by Cheapflights users on 9/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/258:50 amMDW - BNA
Nonstop1h 30mSouthwest
Thu 1/19:00 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 9/29$97

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 September 29, 2025.
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

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 11/6

2:20 pm-12:15 am

1 stop8h 55m

Louisville Intl

Mon 11/10

12:25 pm-8:35 pm

2 stops9h 10m

$108

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/30

2:02 pm-3:46 pm

Nonstop1h 44m

Nashville Intl

Fri 10/31

8:00 am-9:50 am

Nonstop1h 50m

$127

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 10/31

12:55 pm-6:25 pm

1 stop5h 30m

Nashville Intl

Sun 11/2

5:40 am-7:20 am

Nonstop1h 40m

$137

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 12/6

7:35 pm-9:24 pm

Nonstop1h 49m

Nashville Intl

Tue 12/9

3:10 pm-5:08 pm

Nonstop1h 58m

$139

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Sat 11/8

5:50 am-7:20 am

Nonstop1h 30m

Nashville Intl

Sat 11/8

10:00 am-11:45 am

Nonstop1h 45m

$139

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 12/6

1:45 pm-3:20 pm

Nonstop1h 35m

Nashville Intl

Tue 12/9

10:20 am-12:15 pm

Nonstop1h 55m

$139

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/30

1:30 pm-9:00 pm

2 stops7h 30m

Nashville Intl

Fri 10/31

2:35 pm-4:25 pm

Nonstop1h 50m

$142

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 10/30

5:20 pm-10:15 pm

1 stop4h 55m

Nashville Intl

Fri 10/31

6:30 am-11:45 am

1 stop5h 15m

$147

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 11/1

2:02 pm-3:54 pm

Nonstop1h 52m

Nashville Intl

Mon 11/3

6:07 am-8:05 am

Nonstop1h 58m

$148

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 11/24

5:52 pm-7:33 pm

Nonstop1h 41m

Nashville Intl

Fri 11/28

6:21 pm-8:25 pm

Nonstop2h 04m

$148

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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 September 29, 2025.

When flying from Chicago to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 29, 2025.

The most flights from CHI to USKY are scheduled on a Friday (42 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 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 September 29, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American 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
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Contour
7.2
Good
36 reviews
Southwest
8.0
Very good
4,246 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 38m. The distance from Chicago to Kentucky is about 323 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 $39. However, be on the lookout for offers from Frontier 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 - Cincinnati Cinci./N. Kentucky.

  • 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: Alaska Airlines (90%), Envoy Air (89%), Japan Airlines (89%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $66. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $68 on average, our data indicates $294 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, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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.
O'Hare Intl to John F Kennedy Intl flights
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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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$106Average$141FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$121Average$279FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$124Average$548FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$331FlexibilityNo cancel feeOn-time69%

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