HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Kentucky

$38+ Cheap flights from Chicago (CHI) to Kentucky

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/19. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Kentucky with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Kentucky

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kentucky (USKY). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$38
(Trip.com)

Good round-trip deal

$197 or less

Good one-way deal

$99 or less
From Chicago (CHI) to Kentucky
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

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 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/263:50 pmORD - BNA
Nonstop1h 39mFrontier
Sat 3/14:54 pmBNA - ORD
Nonstop1h 58mFrontier
Deal found 1/20$52
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/275:15 amORD - BNA
1 stop8h 54mMultiple Airlines
Wed 3/56:29 pmBNA - ORD
Nonstop1h 58mMultiple Airlines
Deal found 1/20$106
This Frontier deal was found by Cheapflights users on 1/20. 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 3/1012:49 pmMDW - CVG
1 stop11h 33mFrontier
Tue 3/117:10 amCVG - MDW
1 stop9h 03mFrontier
Deal found 1/20$110
This Frontier deal was found by Cheapflights users on 1/20. 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 4/76:40 amMDW - BNA
1 stop6h 28mFrontier
Thu 4/1012:58 pmBNA - MDW
1 stop11h 23mFrontier
Deal found 1/20$110
This Mytrip deal was found by Cheapflights users on 1/19. 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 3/57:18 pmORD - CVG
1 stop14h 40mFrontier
Wed 3/125:36 amCVG - ORD
1 stop6h 21mFrontier
Deal found 1/19$115
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/196:25 amMDW - BNA
Nonstop1h 35mSouthwest
Wed 2/262:30 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 1/20$117
This United Airlines deal was found by Cheapflights users on 1/21. 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 2/187:43 pmORD - BNA
Nonstop1h 39mUnited Airlines
Tue 2/2510:05 amBNA - ORD
Nonstop2h 00mUnited Airlines
Deal found 1/21$127
This Southwest deal was found by Cheapflights users on 1/21. 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 2/138:20 pmMDW - CVG
Nonstop1h 10mSouthwest
Mon 2/177:00 amCVG - MDW
Nonstop1h 15mSouthwest
Deal found 1/21$137
This United Airlines deal was found by Cheapflights users on 1/21. 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.
Mon 3/1010:55 amORD - CVG
Nonstop1h 17mUnited Airlines
Tue 3/1111:23 amCVG - ORD
Nonstop1h 31mUnited Airlines
Deal found 1/21$137
This Southwest deal was found by Cheapflights users on 1/19. 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.
Tue 2/187:00 amORD - BNA
Nonstop1h 30mSouthwest
Fri 2/218:30 pmBNA - ORD
Nonstop1h 50mSouthwest
Deal found 1/19$137
This American Airlines deal was found by Cheapflights users on 1/21. 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.
Tue 2/255:55 pmORD - SDF
Nonstop1h 19mAmerican Airlines
Thu 2/2712:36 pmSDF - ORD
Nonstop1h 40mAmerican Airlines
Deal found 1/21$137
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Mon 3/108:09 pmORD - CVG
Nonstop1h 23mAmerican Airlines
Tue 3/117:04 amCVG - ORD
Nonstop1h 26mAmerican Airlines
Deal found 1/20$138

Find flights from Chicago to Kentucky within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 2/15

2:15 pm-3:54 pm

Nonstop1h 39m

Nashville Intl

Wed 2/19

6:29 pm-8:27 pm

Nonstop1h 58m

$49

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 2/27

5:15 am-2:09 pm

1 stop8h 54m

Nashville Intl

Wed 3/5

6:29 pm-8:27 pm

Nonstop1h 58m

$106

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Mon 3/10

12:49 pm-1:22 am

1 stop11h 33m

Cincinnati Cinci./N. Kentucky

Tue 3/11

7:10 am-3:13 pm

1 stop9h 03m

$110

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 4/7

6:40 am-1:08 pm

1 stop6h 28m

Nashville Intl

Thu 4/10

12:58 pm-12:21 am

1 stop11h 23m

$110

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 3/5

7:18 pm-10:58 am

1 stop14h 40m

Cincinnati Cinci./N. Kentucky

Wed 3/12

5:36 am-10:57 am

1 stop6h 21m

$115

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/19

3:10 pm-4:40 pm

Nonstop1h 30m

Nashville Intl

Wed 2/26

2:55 pm-4:45 pm

Nonstop1h 50m

$117

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 2/19

6:25 am-8:00 am

Nonstop1h 35m

Nashville Intl

Wed 2/26

2:30 pm-4:05 pm

Nonstop1h 35m

$117

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Tue 2/25

10:01 am-11:36 am

Nonstop1h 35m

Nashville Intl

Thu 2/27

5:30 am-7:15 am

Nonstop1h 45m

$127

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Mon 3/10

10:55 am-1:12 pm

Nonstop1h 17m

Cincinnati Cinci./N. Kentucky

Tue 3/11

11:23 am-11:54 am

Nonstop1h 31m

$137

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 2/25

5:55 pm-8:14 pm

Nonstop1h 19m

Louisville Intl

Thu 2/27

12:36 pm-1:16 pm

Nonstop1h 40m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Chicago to Kentucky

Get recent, data-driven insights about flights from Chicago to Kentucky including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.

The most flights from CHI to USKY are scheduled on a Monday (32 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).

Rainfall in Kentucky by month

Plan your trip to Kentucky by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kentucky ranges from 3.1 - 5.3 inches per month. May is typically the wettest month, when rainfall can reach 5.3 in. September is typically the driest time to visit Kentucky when rainfall is around 3.1 in.

Temperature in Kentucky by month

Plan your trip to Kentucky by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kentucky, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 78.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 35.6 F).

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 21, 2025.
To help decide which airline to fly from Chicago to Kentucky, see what other customers have to say about Frontier, United Airlines and Southwest. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,984 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.2

Crew

8.7

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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.

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

    The cheapest airline one-way is Frontier, with whom users have recently found tickets for as low as $55. However, be on the lookout for offers from Southwest 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 O'Hare Intl - Knoxville McGhee Tyson or Chicago Midway - Nashville Intl.

  • 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: Envoy Air (92%), Iberia (91%), Qatar Airways (90%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $98. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $105 on average our data indicates $278 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 Las Vegas flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
O'Hare Intl to LaGuardia flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Boston flights
Midway to Las Vegas flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Newark flights
Midway to Orlando flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Atlanta flights
Midway to Miami flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Austin flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to San Diego flights
Midway to Newark flights
Midway to Los Angeles flights
O'Hare Intl to Nashville flights
O'Hare Intl to West Palm Beach flights
Midway to Atlanta flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Philadelphia flights
Midway to Hobby flights
Midway to Tampa flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Charleston flights
O'Hare Intl to Reagan-National flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
Midway to Denver flights
O'Hare Intl to Palm Springs flights
St. Louis to Las Vegas flights
O'Hare Intl to Hobby flights
O'Hare Intl to Ontario flights
Midway to Fort Myers flights
Midway to San Francisco flights

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 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$141FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$105Average$300FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$261FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.