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Kentucky

$49+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
dic. 18 — dic. 251
jue. 12/18
jue. 12/25
1 adult, Economy
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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 noviembre 18, 2025.

This Super.com deal was found by Cheapflights users on 11/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/216:13 amORD - BNA
Nonstop1h 37mFrontier
mar. 11/258:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 11/17$84
This Kiwi.com deal was found by Cheapflights users on 11/18. 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.
mar. 11/256:13 amORD - BNA
Nonstop1h 37mFrontier
vie. 11/288:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 11/18$89
This Southwest deal was found by Cheapflights users on 11/16. 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.
jue. 12/251:45 pmORD - BNA
Nonstop1h 35mSouthwest
jue. 1/110:20 amBNA - ORD
Nonstop1h 55mSouthwest
Deal found 11/16$97
This Southwest deal was found by Cheapflights users on 11/17. 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.
jue. 12/256:35 amMDW - BNA
Nonstop1h 30mSouthwest
jue. 1/111:05 amBNA - MDW
Nonstop1h 40mSouthwest
Deal found 11/17$97
This Super.com deal was found by Cheapflights users on 11/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/246:13 amORD - BNA
Nonstop1h 37mFrontier
vie. 11/288:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 11/17$108
This Frontier deal was found by Cheapflights users on 11/18. 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.
jue. 12/42:18 pmORD - CVG
1 stop7h 30mFrontier
lun. 12/811:53 amCVG - ORD
1 stop11h 31mFrontier
Deal found 11/18$110
This Super.com deal was found by Cheapflights users on 11/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/216:13 amORD - BNA
Nonstop1h 37mFrontier
vie. 11/288:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 11/17$120
This Kiwi.com deal was found by Cheapflights users on 11/16. 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.
vie. 11/216:13 amORD - BNA
Nonstop1h 37mMultiple Airlines
lun. 11/243:28 pmBNA - ORD
1 stop7h 38mMultiple Airlines
Deal found 11/16$122
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
vie. 11/216:13 amORD - BNA
Nonstop1h 37mFrontier
dom. 11/231:34 pmBNA - ORD
1 stop21h 37mFrontier
Deal found 11/17$123
This Southwest deal was found by Cheapflights users on 11/17. 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.
mié. 12/178:30 pmMDW - BNA
Nonstop1h 30mSouthwest
mié. 12/2411:05 amBNA - MDW
Nonstop1h 40mSouthwest
Deal found 11/17$127
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
jue. 12/116:15 amORD - CVG
1 stop13h 15mMultiple Airlines
lun. 12/152:23 pmCVG - ORD
1 stop21h 45mMultiple Airlines
Deal found 11/17$143
This Kiwi.com deal was found by Cheapflights users on 11/17. 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.
vie. 12/121:34 pmORD - CVG
1 stop8h 14mMultiple Airlines
lun. 12/152:23 pmCVG - ORD
1 stop21h 45mMultiple Airlines
Deal found 11/17$149

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 noviembre 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$97
(Southwest)

One-way from

$49
(United Airlines)

Popular in

February

Cheapest in

August

Average price

$275

Good round-trip deal

$151 or less

Good one-way deal

$79 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 (CHI) to Kentucky
Search Deals
One-way flight from Chicago (CHI) to Kentucky
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($55 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Kentucky.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Kentucky.
Search Deals

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 noviembre 18, 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

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

sáb. 1/17

12:45 pm-6:05 pm

1 stop5h 20m

Nashville Intl

mar. 1/20

4:25 pm-6:05 pm

Nonstop1h 40m

$107

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

sáb. 1/17

1:45 pm-3:20 pm

Nonstop1h 35m

Nashville Intl

mar. 1/20

4:05 pm-9:50 pm

1 stop5h 45m

$107

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

mié. 12/17

12:45 pm-2:28 pm

Nonstop1h 43m

Nashville Intl

mié. 12/24

8:00 am-9:55 am

Nonstop1h 55m

$127

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

jue. 1/15

2:15 pm-9:00 pm

1 stop6h 45m

Nashville Intl

sáb. 1/17

10:20 am-12:15 pm

Nonstop1h 55m

$144

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

jue. 12/4

5:05 am-10:49 am

1 stop4h 44m

Cincinnati Cinci./N. Kentucky

sáb. 12/6

5:05 am-1:16 pm

1 stop9h 11m

$150

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

jue. 1/15

2:15 pm-9:00 pm

1 stop6h 45m

Nashville Intl

dom. 1/18

6:05 am-1:00 pm

1 stop6h 55m

$154

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

jue. 12/25

3:25 pm-10:47 pm

1 stop6h 22m

Louisville Intl

mié. 12/31

1:52 pm-5:26 pm

1 stop4h 34m

$157

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

jue. 12/25

4:01 pm-11:03 pm

1 stop6h 02m

Louisville Intl

mié. 12/31

7:25 am-12:54 pm

1 stop6h 29m

$157

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

jue. 12/25

5:54 pm-8:32 pm

Nonstop1h 38m

Louisville Intl

mié. 12/31

9:05 am-9:49 am

Nonstop1h 44m

$157

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

sáb. 1/10

5:50 am-9:50 pm

2 stops15h 00m

Cincinnati Cinci./N. Kentucky

lun. 1/12

9:20 pm-12:42 pm

1 stop16h 22m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

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 $106). Flying from Chicago to Kentucky in January is currently the most expensive (average of $191). 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 noviembre 18, 2025.

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 11% 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 December 16, 2024.

Travelers seeking maximum savings on their Chicago to Kentucky flight should consider departing on Sunday mornings 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 noviembre 18, 2025.

The most flights from CHI to USKY are scheduled on a Monday (39 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 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 noviembre 18, 2025.
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
4,246 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
7.5
Good
41 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
9,019 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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
11,046 reviews
Southwest
8.0
Very good
4,246 reviews

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

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 43m. The distance from Chicago to Kentucky is about 410 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 $49. However, be on the lookout for offers from United Airlines and Frontier, 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 O'Hare Intl - Knoxville McGhee Tyson 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: Japan Airlines (93%), Envoy Air (89%), Alaska Airlines (87%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $45. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $97 on average, our data indicates $248 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 $106). Flying from Chicago to Kentucky in January is currently the most expensive (average of $191). 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 noviembre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$114Average$144FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$129Average$511FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$134Average$285FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$329FlexibilityNo cancel feeOn-time69%

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