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Kentucky

$49+ Cheap flights from Illinois 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SDF
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Illinois to Kentucky

Keep the following information in mind while searching for Illinois to Kentucky flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$83
(Frontier)

One-way from

$49
(United Airlines)

Popular in

February

Cheapest in

August

Average price

$291

Good round-trip deal

$106 or less

Good one-way deal

$58 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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One-way flight from Illinois to Kentucky
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Highest demand for flights based on searches. 16% potential increase in price ($61 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:06 pmORD - BNA
Nonstop1h 48mFrontier
Mon 11/248:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 10/28$77
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:20 amORD - BNA
Nonstop1h 36mFrontier
Mon 11/178:51 amBNA - ORD
Nonstop1h 51mFrontier
Deal found 10/28$81
This Frontier deal was found by Cheapflights users on 10/28. 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.
Thu 11/208:59 amORD - BNA
1 stop10h 52mFrontier
Mon 11/248:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 10/28$82
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/179:32 amORD - BNA
1 stop9h 39mFrontier
Mon 11/248:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 10/30$83
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:20 amORD - BNA
Nonstop1h 36mFrontier
Thu 11/208:46 pmBNA - ORD
1 stop11h 00mFrontier
Deal found 10/28$86
This Flightnetwork deal was found by Cheapflights users on 10/28. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:06 pmORD - BNA
Nonstop1h 48mFrontier
Mon 11/178:51 amBNA - ORD
Nonstop1h 51mFrontier
Deal found 10/28$91
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Mon 11/106:20 amORD - BNA
Nonstop1h 36mFrontier
Thu 11/138:49 pmBNA - ORD
Nonstop1h 48mFrontier
Deal found 10/27$92
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/158:00 amORD - BNA
1 stop26h 15mFrontier
Mon 11/178:51 amBNA - ORD
Nonstop1h 51mFrontier
Deal found 10/28$94
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:13 amORD - BNA
Nonstop1h 37mFrontier
Fri 11/288:45 amBNA - ORD
Nonstop1h 53mFrontier
Deal found 10/29$95
This Southwest deal was found by Cheapflights users on 10/29. 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 12/41:45 pmORD - BNA
Nonstop1h 35mSouthwest
Mon 12/810:20 amBNA - ORD
Nonstop1h 55mSouthwest
Deal found 10/29$97
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:30 pmMDW - BNA
Nonstop1h 30mSouthwest
Mon 12/87:40 amBNA - MDW
Nonstop1h 45mSouthwest
Deal found 10/28$97
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:20 pmORD - SDF
Nonstop1h 36mAmerican Airlines
Mon 12/86:21 pmSDF - ORD
Nonstop1h 55mAmerican Airlines
Deal found 10/30$97

Cheapflights Fare Finder

 
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 October 30, 2025.
Use the filters below to find and compare flights from Illinois to Kentucky that are best for you.

Fly from

Illinois

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 12/4

1:45 pm-3:20 pm

Nonstop1h 35m

Nashville Intl

Mon 12/8

10:20 am-12:15 pm

Nonstop1h 55m

$97

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 12/4

7:20 am-9:03 am

Nonstop1h 43m

Nashville Intl

Mon 12/8

11:19 am-1:15 pm

Nonstop1h 56m

$97

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 1/22

2:13 pm-3:54 pm

Nonstop1h 41m

Nashville Intl

Mon 1/26

8:00 am-9:55 am

Nonstop1h 55m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 1/22

10:05 am-11:40 am

Nonstop1h 35m

Nashville Intl

Mon 1/26

7:25 am-9:10 am

Nonstop1h 45m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Thu 12/4

5:50 am-7:20 am

Nonstop1h 30m

Nashville Intl

Mon 12/8

6:35 pm-8:15 pm

Nonstop1h 40m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 12/23

6:50 pm-8:20 pm

Nonstop1h 30m

Nashville Intl

Tue 12/30

3:45 pm-7:10 pm

1 stop3h 25m

$103

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Tue 12/9

5:35 am-7:05 am

Nonstop1h 30m

Nashville Intl

Wed 12/10

5:50 am-11:20 am

1 stop5h 30m

$107

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 1/26

2:15 pm-8:55 pm

1 stop6h 40m

Nashville Intl

Wed 1/28

6:05 am-1:00 pm

1 stop6h 55m

$117

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Tue 12/9

2:15 pm-9:25 pm

1 stop7h 10m

Nashville Intl

Wed 12/10

1:30 pm-9:50 pm

2 stops8h 20m

$122

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Mon 1/26

2:35 pm-7:35 pm

1 stop5h 00m

Nashville Intl

Wed 1/28

12:40 pm-7:00 pm

2 stops6h 20m

$122

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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.

Cheapflights Insights

Everything you need to know about your flight from Illinois to Kentucky

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

Currently, October is the cheapest month in which you can book a flight from Illinois to Kentucky (average of $95). Flying from Illinois to Kentucky in June is currently the most expensive (average of $177). 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 October 30, 2025.

It’s optimal to fly from Illinois to Kentucky in the evening. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight at noon.

What is the cheapest day to fly from Illinois to Kentucky?

Use this chart to determine the cheapest time to fly round-trip from Illinois to Kentucky. Price data was last updated on November 3, 2024.

Travelers seeking maximum savings on their Illinois to Kentucky flight should consider departing on Sunday mornings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Illinois 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 October 30, 2025.
Peruse reviews from past customers who have flown with Southwest, Contour, and United Airlines from Illinois to Kentucky to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Contour
7.5
Good
40 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,995 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,034 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Illinois to Kentucky?

    There are many flights that can get you from Illinois to Kentucky in 1h 35m. Fly via Southwest, United Airlines, or Delta to get the fastest option. The distance between Illinois and Kentucky is about 410 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 Southwest. You may also be able to find cheap deals on United Airlines and Allegiant Air, with prices starting from $49 and $60, 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, October is the cheapest month in which you can book a flight from Illinois to Kentucky (average of $95). Flying from Illinois to Kentucky in June is currently the most expensive (average of $177). 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$114Average$143FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$124Average$532FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$134Average$291FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$323FlexibilityNo cancel feeOn-time69%

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