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$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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$94
(Booking.com)

One-way from

$49
(Southwest)

Popular in

February

Cheapest in

August

Average price

$343

Good round-trip deal

$201 or less

Good one-way deal

$63 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. 17% potential increase in price ($62 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 April 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 April 17, 2025.

This Booking.com deal was found by Cheapflights users on 4/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/125:20 pmORD - BNA
Nonstop1h 32mSpirit Airlines
Mon 5/197:39 pmBNA - ORD
1 stop13h 11mSpirit Airlines
Deal found 4/16$94
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/122:10 pmORD - BNA
Nonstop1h 44mUnited Airlines
Wed 5/146:05 amBNA - ORD
Nonstop2h 00mUnited Airlines
Deal found 4/17$97
This Southwest deal was found by Cheapflights users on 4/16. 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.
Mon 5/125:20 amMDW - BNA
Nonstop1h 25mSouthwest
Mon 5/199:25 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 4/16$97
This CheapOair deal was found by Cheapflights users on 4/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/812:35 pmORD - BNA
Nonstop1h 42mMultiple Airlines
Mon 6/92:28 pmBNA - ORD
Nonstop1h 57mMultiple Airlines
Deal found 4/17$100
This Southwest deal was found by Cheapflights users on 4/16. 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.
Wed 5/145:45 pmORD - BNA
1 stop5h 20mSouthwest
Wed 5/2110:50 amBNA - ORD
Nonstop1h 55mSouthwest
Deal found 4/16$107
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/52:36 pmORD - BNA
Nonstop1h 36mFrontier
Mon 5/125:02 pmBNA - ORD
Nonstop2h 04mFrontier
Deal found 4/16$109
This American Airlines deal was found by Cheapflights users on 4/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/610:14 pmORD - BNA
Nonstop1h 34mAmerican Airlines
Mon 6/95:36 amBNA - ORD
Nonstop1h 51mAmerican Airlines
Deal found 4/17$149
This Frontier deal was found by Cheapflights users on 4/16. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/151:19 pmMDW - CVG
1 stop10h 40mFrontier
Fri 5/165:45 amCVG - MDW
1 stop7h 39mFrontier
Deal found 4/16$160
This Frontier deal was found by Cheapflights users on 4/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/109:19 amORD - CVG
1 stop10h 33mFrontier
Sun 5/117:51 pmCVG - ORD
1 stop10h 19mFrontier
Deal found 4/17$160
This CheapOair deal was found by Cheapflights users on 4/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:19 pmMDW - BNA
1 stop19h 50mFrontier
Sun 5/117:52 pmBNA - MDW
1 stop23h 16mFrontier
Deal found 4/16$161
This United Airlines deal was found by Cheapflights users on 4/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/47:00 amORD - SDF
Nonstop1h 33mUnited Airlines
Wed 6/42:05 pmSDF - ORD
Nonstop1h 40mUnited Airlines
Deal found 4/17$171
This Southwest deal was found by Cheapflights users on 4/16. 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.
Wed 6/256:55 amMDW - SDF
1 stop5h 25mSouthwest
Sat 6/286:00 pmSDF - MDW
Nonstop1h 20mSouthwest
Deal found 4/16$171

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 April 17, 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

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 5/12

5:20 pm-6:52 pm

Nonstop1h 32m

Nashville Intl

Mon 5/19

7:39 pm-8:50 am

1 stop13h 11m

$94

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 5/12

4:00 pm-5:40 pm

Nonstop1h 40m

Nashville Intl

Tue 5/13

10:50 am-12:45 pm

Nonstop1h 55m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 5/12

5:20 am-6:45 am

Nonstop1h 25m

Nashville Intl

Mon 5/19

9:25 pm-11:00 pm

Nonstop1h 35m

$97

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 6/8

12:35 pm-2:17 pm

Nonstop1h 42m

Nashville Intl

Mon 6/9

2:28 pm-4:25 pm

Nonstop1h 57m

$100

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 5/5

2:36 pm-4:12 pm

Nonstop1h 36m

Nashville Intl

Mon 5/12

5:02 pm-7:06 pm

Nonstop2h 04m

$109

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 5/9

3:40 pm-5:28 pm

Nonstop1h 48m

Nashville Intl

Tue 5/13

9:58 am-11:50 am

Nonstop1h 52m

$121

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 6/6

10:14 pm-11:48 pm

Nonstop1h 34m

Nashville Intl

Mon 6/9

5:36 am-7:27 am

Nonstop1h 51m

$149

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 5/15

1:19 pm-12:59 am

1 stop10h 40m

Cincinnati Cinci./N. Kentucky

Fri 5/16

5:45 am-12:24 pm

1 stop7h 39m

$160

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Sat 5/10

9:19 am-8:52 pm

1 stop10h 33m

Cincinnati Cinci./N. Kentucky

Sun 5/11

7:51 pm-5:10 am

1 stop10h 19m

$160

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 5/8

1:19 pm-9:09 am

1 stop19h 50m

Nashville Intl

Sun 5/11

7:52 pm-7:08 pm

1 stop23h 16m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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, 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 April 17, 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 April 17, 2025.

The most flights from CHI to USKY are scheduled on a Wednesday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 April 17, 2025.
To help decide which airline to fly from Chicago to Kentucky, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,916 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,667 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,280 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 Southwest, with whom users have recently found tickets for as low as $49. However, be on the lookout for offers from American 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 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: Copa Airlines (94%), Air Wisconsin (86%), Royal Jordanian (81%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $60. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $70 on average our data indicates $271 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.
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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$102Average$145FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$303FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$275FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$157Average$539FlexibilityNo cancel feeOn-time63%

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