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$38+ Cheap flights from Illinois 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SDF
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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Cheap flight deals from Illinois to Kentucky

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) 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 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$38
(Frontier)

Popular in

April

Cheapest in

August

Average price

$275

Good round-trip deal

$219 or less

Good one-way deal

$85 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 Illinois to Kentucky
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Highest demand for flights based on searches. 10% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2025
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Price to beat on a round-trip flight from Illinois to Kentucky.
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Price to beat on a one-way flight from Illinois to Kentucky.
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Find flight deals from Illinois to Kentucky

Cheapest flights from Illinois to Kentucky
Explore the most affordable flight options available from Illinois to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2025.

This Frontier deal was found by Cheapflights users on 1/28. 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 3/313:22 pmORD - BNA
Nonstop1h 39mFrontier
Fri 4/42:08 pmBNA - ORD
Nonstop1h 53mFrontier
Deal found 1/28$53
This Priceline deal was found by Cheapflights users on 1/29. 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 2/263:50 pmORD - BNA
Nonstop1h 39mMultiple Airlines
Wed 3/59:15 pmBNA - ORD
1 stop10h 29mMultiple Airlines
Deal found 1/29$71
This Cheapflightsfares deal was found by Cheapflights users on 1/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/76:45 amMDW - BNA
1 stop6h 23mFrontier
Wed 4/96:00 pmBNA - MDW
1 stop6h 21mFrontier
Deal found 1/30$108
This Mytrip deal was found by Cheapflights users on 1/28. 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.
Thu 2/204:04 pmMDW - CVG
1 stop6h 22mFrontier
Mon 2/247:59 pmCVG - MDW
1 stop10h 32mFrontier
Deal found 1/28$109
This Frontier deal was found by Cheapflights users on 1/29. 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 2/206:20 amORD - CVG
1 stop16h 06mFrontier
Mon 2/247:04 pmCVG - ORD
1 stop6h 40mFrontier
Deal found 1/29$110
This Mytrip deal was found by Cheapflights users on 1/29. 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 2/267:07 amORD - BNA
2 stops14h 48mSpirit Airlines
Wed 3/59:15 pmBNA - ORD
1 stop10h 29mSpirit Airlines
Deal found 1/29$112
This Southwest deal was found by Cheapflights users on 1/29. 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 2/2610:25 amMDW - BNA
Nonstop1h 30mSouthwest
Wed 3/57:20 amBNA - MDW
Nonstop1h 35mSouthwest
Deal found 1/29$127
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Sat 3/15:30 pmORD - BNA
Nonstop1h 31mAmerican Airlines
Tue 3/45:00 pmBNA - ORD
Nonstop1h 44mAmerican Airlines
Deal found 1/29$128
This United Airlines deal was found by Cheapflights users on 1/30. 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 2/252:25 pmORD - CVG
Nonstop1h 20mUnited Airlines
Wed 2/262:10 pmCVG - ORD
Nonstop1h 25mUnited Airlines
Deal found 1/30$137
This Southwest deal was found by Cheapflights users on 1/29. 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 2/277:00 amORD - BNA
Nonstop1h 30mSouthwest
Mon 3/38:30 pmBNA - ORD
Nonstop1h 50mSouthwest
Deal found 1/29$137
This United Airlines deal was found by Cheapflights users on 1/29. 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 2/257:55 pmORD - SDF
Nonstop1h 31mUnited Airlines
Wed 2/2610:05 amSDF - ORD
Nonstop1h 48mUnited Airlines
Deal found 1/29$137
This Southwest deal was found by Cheapflights users on 1/29. 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 2/194:50 pmMDW - SDF
Nonstop1h 10mSouthwest
Thu 2/207:15 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 1/29$137

Find flights from Illinois to Kentucky within your budget

Customize your flight search to find flights from Illinois 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 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 3/5

3:50 pm-5:29 pm

Nonstop1h 39m

Nashville Intl

Mon 3/10

2:03 pm-4:01 pm

Nonstop1h 58m

$51

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/26

3:50 pm-5:29 pm

Nonstop1h 39m

Nashville Intl

Wed 3/5

9:15 pm-7:44 am

1 stop10h 29m

$71

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 4/7

6:45 am-1:08 pm

1 stop6h 23m

Nashville Intl

Wed 4/9

6:00 pm-12:21 am

1 stop6h 21m

$108

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/20

4:04 pm-11:26 pm

1 stop6h 22m

Cincinnati Cinci./N. Kentucky

Mon 2/24

7:59 pm-5:31 am

1 stop10h 32m

$109

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/20

6:20 am-11:26 pm

1 stop16h 06m

Cincinnati Cinci./N. Kentucky

Mon 2/24

7:04 pm-12:44 am

1 stop6h 40m

$110

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 2/26

3:14 pm-9:55 pm

1 stop6h 41m

Nashville Intl

Wed 3/5

9:15 pm-7:44 am

1 stop10h 29m

$123

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 3/1

10:01 am-11:36 am

Nonstop1h 35m

Nashville Intl

Tue 3/4

7:10 am-8:57 am

Nonstop1h 47m

$128

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 2/25

2:25 pm-4:45 pm

Nonstop1h 20m

Cincinnati Cinci./N. Kentucky

Wed 2/26

2:10 pm-2:35 pm

Nonstop1h 25m

$137

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 4/10

5:20 am-6:45 am

Nonstop1h 25m

Nashville Intl

Mon 4/14

4:30 pm-6:05 pm

Nonstop1h 35m

$137

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Tue 3/25

12:45 pm-2:26 pm

Nonstop1h 41m

Nashville Intl

Tue 4/1

8:00 am-9:51 am

Nonstop1h 51m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Kentucky

Have a flexible travel schedule? Discover the best time to fly to Kentucky from Illinois 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 Illinois to Kentucky

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

What is the cheapest month to book a flight from Illinois to Kentucky?

Currently, January is the cheapest month in which you can book a flight from Illinois to Kentucky (average of $299). Flying from Illinois 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 IL to KY?

Find hourly flight availability from Illinois 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 30, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Kentucky as you normally would.

Weekly flight availability from Illinois to Kentucky

Explore weekly flight availability from Illinois 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 30, 2025.

The most flights from USIL to USKY are scheduled on a Thursday (27 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 January 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue from Illinois to Kentucky to help guide your decision. 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
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

JetBlue
7.4
Good
3,153 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
8,906 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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
7.3
Good
790 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 Illinois 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 Illinois to Kentucky one-way?

    $49 is the cheapest one-way deal found within the past few days, from Sun Country Air. You may also be able to find cheap deals on Frontier and Spirit Airlines, with prices starting from $50 and $63, respectively.

  • Can I find deals for flights from Illinois to Kentucky that include hotel bookings?

    Yes. In addition to deals on Illinois to Kentucky flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Illinois to Kentucky?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Illinois to Kentucky.

  • Can I find deals for business class flights from Illinois to Kentucky?

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Kentucky?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Kentucky (average of $299). Flying from Illinois 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 Illinois 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 Illinois to Kentucky

Discover the top 4 airlines that operate flights from Illinois 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 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$141FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$105Average$300FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$276FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$118Average$532FlexibilityNo cancel feeOn-time63%
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