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Kentucky

$44+ 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 8/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
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 July 11, 2025.

Round-trip from

$86
(Frontier)

One-way from

$44
(Cheapflightsfares)

Popular in

February

Cheapest in

August

Average price

$292

Good round-trip deal

$148 or less

Good one-way deal

$64 or less
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 ($58 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 July 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 July 11, 2025.

This Frontier deal was found by Cheapflights users on 7/9. 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 7/2812:35 pmORD - BNA
Nonstop1h 39mFrontier
Thu 7/313:07 pmBNA - ORD
Nonstop2h 04mFrontier
Deal found 7/9$86
This Expedia deal was found by Cheapflights users on 7/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/265:38 pmORD - BNA
1 stop6h 03mSpirit Airlines
Fri 8/17:27 pmBNA - ORD
Nonstop2h 03mSpirit Airlines
Deal found 7/10$87
This Southwest deal was found by Cheapflights users on 7/10. 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 8/216:45 pmMDW - CVG
Nonstop1h 10mSouthwest
Mon 8/256:40 amCVG - MDW
Nonstop1h 10mSouthwest
Deal found 7/10$91
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/612:55 pmORD - CVG
Nonstop1h 26mUnited Airlines
Thu 8/77:00 amCVG - ORD
Nonstop1h 35mUnited Airlines
Deal found 7/8$91
This Southwest deal was found by Cheapflights users on 7/10. 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 8/143:30 pmMDW - SDF
Nonstop1h 10mSouthwest
Sun 8/177:10 pmSDF - MDW
Nonstop1h 20mSouthwest
Deal found 7/10$91
This Southwest deal was found by Cheapflights users on 7/10. 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.
Fri 8/85:40 amMDW - BNA
Nonstop1h 25mSouthwest
Mon 8/115:25 amBNA - MDW
Nonstop1h 35mSouthwest
Deal found 7/10$91
This Southwest deal was found by Cheapflights users on 7/9. 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.
Fri 9/52:55 pmORD - BNA
Nonstop1h 35mSouthwest
Mon 9/82:35 pmBNA - ORD
Nonstop1h 50mSouthwest
Deal found 7/9$91
This American Airlines deal was found by Cheapflights users on 7/10. 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.
Wed 8/63:13 pmORD - SDF
Nonstop1h 25mAmerican Airlines
Sat 8/96:44 amSDF - ORD
Nonstop1h 46mAmerican Airlines
Deal found 7/10$97
This CheapOair deal was found by Cheapflights users on 7/10. 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 8/215:16 pmORD - BNA
1 stop6h 04mMultiple Airlines
Fri 8/229:54 pmBNA - ORD
Nonstop2h 01mMultiple Airlines
Deal found 7/10$100
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Wed 9/33:31 pmORD - CVG
Nonstop1h 20mAmerican Airlines
Sat 9/67:00 amCVG - ORD
Nonstop1h 26mAmerican Airlines
Deal found 7/9$101
This American Airlines deal was found by Cheapflights users on 7/9. 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 8/51:17 pmORD - BNA
Nonstop1h 35mAmerican Airlines
Tue 8/121:21 pmBNA - ORD
Nonstop1h 56mAmerican Airlines
Deal found 7/9$102
This Southwest deal was found by Cheapflights users on 7/10. 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 10/11:50 pmORD - CVG
1 stop7h 35mSouthwest
Wed 10/85:40 amCVG - ORD
1 stop7h 10mSouthwest
Deal found 7/10$111

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 July 11, 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 7/28

12:35 pm-2:14 pm

Nonstop1h 39m

Nashville Intl

Thu 7/31

3:07 pm-5:11 pm

Nonstop2h 04m

$86

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 7/26

5:38 pm-11:41 pm

1 stop6h 03m

Nashville Intl

Fri 8/1

7:27 pm-9:30 pm

Nonstop2h 03m

$87

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 7/28

12:35 pm-2:14 pm

Nonstop1h 39m

Nashville Intl

Sat 8/2

1:58 pm-11:27 pm

1 stop9h 29m

$89

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 8/21

6:45 pm-8:55 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Mon 8/25

6:40 am-6:50 am

Nonstop1h 10m

$91

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 8/6

12:55 pm-3:21 pm

Nonstop1h 26m

Cincinnati Cinci./N. Kentucky

Thu 8/7

7:00 am-7:35 am

Nonstop1h 35m

$91

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Thu 8/14

3:30 pm-5:40 pm

Nonstop1h 10m

Louisville Intl

Sun 8/17

7:10 pm-7:30 pm

Nonstop1h 20m

$91

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Fri 8/8

9:45 pm-11:10 pm

Nonstop1h 25m

Nashville Intl

Mon 8/11

5:25 am-7:00 am

Nonstop1h 35m

$91

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 9/5

2:55 pm-4:30 pm

Nonstop1h 35m

Nashville Intl

Mon 9/8

2:35 pm-4:25 pm

Nonstop1h 50m

$91

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 8/6

3:13 pm-5:38 pm

Nonstop1h 25m

Louisville Intl

Sat 8/9

6:44 am-7:30 am

Nonstop1h 46m

$97

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 9/3

3:31 pm-5:51 pm

Nonstop1h 20m

Cincinnati Cinci./N. Kentucky

Sat 9/6

7:00 am-7:26 am

Nonstop1h 26m

$101

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

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 July 11, 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 July 11, 2025.

The most flights from CHI to USKY are scheduled on a Thursday (43 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 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 July 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, 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
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,951 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,846 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Allegiant Air
7.2
Good
704 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Allegiant Air, with whom users have recently found tickets for as low as $44. However, be on the lookout for offers from Southwest and Spirit 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 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: GoJet (90%), Copa Airlines (89%), Japan Airlines (89%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $60 on average our data indicates $318 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 July 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$102Average$148FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$117Average$270FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$124Average$532FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$137Average$339FlexibilityNo cancel feeOn-time69%

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