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$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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$38
(Cheapflightsfares)

Popular in

April

Cheapest in

August

Average price

$322

Good round-trip deal

$120 or less

Good one-way deal

$61 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
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
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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.
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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 February 20, 2025.

This Frontier deal was found by Cheapflights users on 2/20. 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.
Wed 4/23:22 pmORD - BNA
Nonstop1h 38mFrontier
Fri 4/112:09 pmBNA - ORD
Nonstop1h 53mFrontier
Deal found 2/20$53
This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/123:22 pmORD - BNA
Nonstop1h 39mMultiple Airlines
Wed 3/199:50 pmBNA - ORD
1 stop9h 44mMultiple Airlines
Deal found 2/20$57
This Mytrip deal was found by Cheapflights users on 2/19. 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 3/55:22 pmORD - BNA
1 stop14h 38mSpirit Airlines
Wed 3/129:15 pmBNA - ORD
1 stop10h 29mSpirit Airlines
Deal found 2/19$96
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/26:40 amMDW - BNA
1 stop6h 27mFrontier
Wed 4/166:00 pmBNA - MDW
1 stop6h 21mFrontier
Deal found 2/20$106
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/71:10 pmMDW - CVG
1 stop10h 04mFrontier
Thu 4/1012:23 pmCVG - MDW
1 stop6h 08mFrontier
Deal found 2/19$110
This Frontier deal was found by Cheapflights users on 2/20. 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.
Tue 4/19:22 amORD - CVG
1 stop9h 59mFrontier
Thu 4/37:54 pmCVG - ORD
1 stop10h 00mFrontier
Deal found 2/20$110
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Wed 4/22:45 pmORD - CVG
Nonstop1h 14mAmerican Airlines
Wed 4/92:39 pmCVG - ORD
Nonstop1h 26mAmerican Airlines
Deal found 2/20$117
This Southwest deal was found by Cheapflights users on 2/20. 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 4/234:00 pmORD - BNA
Nonstop1h 40mSouthwest
Mon 4/2810:50 amBNA - ORD
Nonstop1h 55mSouthwest
Deal found 2/20$117
This Southwest deal was found by Cheapflights users on 2/19. 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.
Wed 3/125:40 amMDW - BNA
Nonstop1h 30mSouthwest
Wed 3/199:15 pmBNA - MDW
Nonstop1h 30mSouthwest
Deal found 2/19$117
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/86:01 pmORD - SDF
Nonstop1h 28mUnited Airlines
Thu 4/1011:04 amSDF - ORD
Nonstop1h 36mUnited Airlines
Deal found 2/19$117
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/67:15 amORD - CVG
Nonstop1h 22mUnited Airlines
Mon 3/106:00 amCVG - ORD
Nonstop1h 30mUnited Airlines
Deal found 2/20$118
This Southwest deal was found by Cheapflights users on 2/20. 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.
Tue 4/13:35 pmMDW - CVG
1 stop7h 20mSouthwest
Thu 4/36:30 amCVG - MDW
Nonstop1h 10mSouthwest
Deal found 2/20$127

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 February 20, 2025.

Fly from

Chicago

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 4/2

3:22 pm-5:00 pm

Nonstop1h 38m

Nashville Intl

Fri 4/11

2:09 pm-4:02 pm

Nonstop1h 53m

$53

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 3/12

3:22 pm-5:01 pm

Nonstop1h 39m

Nashville Intl

Wed 3/19

9:50 pm-7:34 am

1 stop9h 44m

$57

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 3/5

5:22 pm-8:00 am

1 stop14h 38m

Nashville Intl

Wed 3/12

9:15 pm-7:44 am

1 stop10h 29m

$96

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 4/2

6:40 am-1:07 pm

1 stop6h 27m

Nashville Intl

Wed 4/16

6:00 pm-12:21 am

1 stop6h 21m

$106

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Mon 4/7

1:10 pm-12:14 am

1 stop10h 04m

Cincinnati Cinci./N. Kentucky

Thu 4/10

12:23 pm-5:31 pm

1 stop6h 08m

$110

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 4/1

9:22 am-8:21 pm

1 stop9h 59m

Cincinnati Cinci./N. Kentucky

Thu 4/3

7:54 pm-4:54 am

1 stop10h 00m

$110

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 4/2

2:45 pm-4:59 pm

Nonstop1h 14m

Cincinnati Cinci./N. Kentucky

Wed 4/9

2:39 pm-3:05 pm

Nonstop1h 26m

$117

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 4/23

4:00 pm-5:40 pm

Nonstop1h 40m

Nashville Intl

Mon 4/28

10:50 am-12:45 pm

Nonstop1h 55m

$117

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 4/8

6:01 pm-8:29 pm

Nonstop1h 28m

Louisville Intl

Thu 4/10

11:04 am-11:40 am

Nonstop1h 36m

$117

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 4/2

8:55 pm-10:25 pm

Nonstop1h 30m

Nashville Intl

Wed 4/9

7:30 pm-9:05 pm

Nonstop1h 35m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

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.

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 February 20, 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 February 20, 2025.

The most flights from CHI to USKY are scheduled on a Thursday (31 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 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 February 20, 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
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $50. However, be on the lookout for offers from Spirit Airlines and Southwest, 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: Iberia (89%), American Airlines (84%), Emirates (83%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $83. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $57 on average our data indicates $287 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$141FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$297FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$263FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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