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Illinois

$46+ Cheap flights from Kentucky to Illinois

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Kentucky to Illinois

Keep the following information in mind while searching for Kentucky to Illinois flight deals. Data was last updated September 17, 2025.

Round-trip from

$78
(Kiwi.com)

One-way from

$46
(Booking.com)

Popular in

March

Cheapest in

April

Average price

$275

Good round-trip deal

$138 or less

Good one-way deal

$95 or less
From Kentucky to Illinois
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One-way flight from Kentucky to Illinois
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High demand for flights, 3% potential price rise
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Kentucky to Illinois.
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Price to beat on a one-way flight from Kentucky to Illinois.
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Find flight deals from Kentucky to Illinois

Cheapest flights from Kentucky to Illinois
Explore the most affordable flight options available from Kentucky to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/312:01 pmBNA - ORD
Nonstop1h 48mMultiple Airlines
Sun 11/26:06 pmORD - BNA
Nonstop1h 48mMultiple Airlines
Deal found 9/15$78
This Orbitz deal was found by Cheapflights users on 9/16. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/239:02 pmBNA - ORD
Nonstop1h 47mMultiple Airlines
Sun 10/2612:41 pmORD - BNA
Nonstop1h 36mMultiple Airlines
Deal found 9/16$79
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/263:21 pmBNA - ORD
Nonstop2h 05mMultiple Airlines
Sun 10/261:26 pmORD - BNA
Nonstop1h 44mMultiple Airlines
Deal found 9/17$80
This Frontier deal was found by Cheapflights users on 9/15. 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 10/63:11 pmBNA - ORD
Nonstop2h 05mFrontier
Thu 10/912:53 pmORD - BNA
Nonstop1h 36mFrontier
Deal found 9/15$87
This Frontier deal was found by Cheapflights users on 9/15. 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 10/212:48 pmBNA - ORD
Nonstop2h 00mFrontier
Mon 10/612:43 pmORD - BNA
Nonstop1h 43mFrontier
Deal found 9/15$88
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/32:59 pmBNA - ORD
Nonstop1h 57mFrontier
Sun 10/512:43 pmORD - BNA
Nonstop1h 43mFrontier
Deal found 9/17$90
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
Sun 11/28:49 pmBNA - ORD
Nonstop1h 48mFrontier
Thu 11/66:06 pmORD - BNA
Nonstop1h 48mFrontier
Deal found 9/15$91
This Frontier deal was found by Cheapflights users on 9/17. 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 11/13:42 pmBNA - ORD
1 stop8h 30mFrontier
Sun 11/26:06 pmORD - BNA
Nonstop1h 48mFrontier
Deal found 9/17$92
This Frontier deal was found by Cheapflights users on 9/16. 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 10/163:24 pmBNA - ORD
Nonstop1h 55mFrontier
Thu 10/2312:53 pmORD - BNA
Nonstop1h 36mFrontier
Deal found 9/16$94
This Priceline deal was found by Cheapflights users on 9/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/32:59 pmBNA - ORD
Nonstop1h 57mFrontier
Mon 10/612:43 pmORD - BNA
Nonstop1h 43mFrontier
Deal found 9/17$96
This Southwest deal was found by Cheapflights users on 9/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/118:55 pmBNA - MDW
Nonstop1h 40mSouthwest
Tue 11/186:15 pmMDW - BNA
Nonstop1h 35mSouthwest
Deal found 9/17$97
This United Airlines deal was found by Cheapflights users on 9/17. 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.
Sat 11/112:10 pmBNA - ORD
Nonstop1h 50mUnited Airlines
Tue 11/49:05 pmORD - BNA
Nonstop1h 44mUnited Airlines
Deal found 9/17$97

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Illinois 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 September 17, 2025.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.

Fly from

Kentucky

Fly to

Illinois

Route

Depart

Return

Price

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 11/1

5:50 am-7:25 am

Nonstop1h 35m

Chicago Midway

Sat 11/1

3:50 pm-5:15 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Tue 11/11

8:00 am-9:50 am

Nonstop1h 50m

Chicago O'Hare Intl

Tue 11/18

10:58 am-12:34 pm

Nonstop1h 36m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 11/12

6:35 pm-8:15 pm

Nonstop1h 40m

Chicago Midway

Tue 11/18

12:25 pm-1:55 pm

Nonstop1h 30m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Sat 11/8

5:40 am-7:20 am

Nonstop1h 40m

Chicago Midway

Mon 11/10

9:35 pm-11:00 pm

Nonstop1h 25m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/10

10:20 am-12:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Sat 12/13

1:45 pm-3:20 pm

Nonstop1h 35m

$97

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 12/4

10:20 am-12:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Tue 12/9

1:45 pm-3:20 pm

Nonstop1h 35m

$97

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 11/19

1:10 pm-4:35 pm

1 stop3h 25m

Chicago Midway

Sat 11/22

5:35 pm-7:05 pm

Nonstop1h 30m

$103

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Thu 12/4

1:10 pm-4:35 pm

1 stop3h 25m

Chicago Midway

Tue 12/9

5:35 am-7:05 am

Nonstop1h 30m

$103

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 11/12

1:10 pm-4:35 pm

1 stop3h 25m

Chicago Midway

Wed 11/19

8:50 am-10:20 am

Nonstop1h 30m

$103

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Tue 11/11

11:05 am-12:45 pm

Nonstop1h 40m

Chicago Midway

Tue 11/18

2:10 pm-5:50 pm

1 stop3h 40m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

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

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

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

Currently, August is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $245). Flying from Kentucky to Illinois in March is currently the most expensive (average of $321). 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 KY to IL?

Find hourly flight availability from Kentucky to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

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

Weekly flight availability from Kentucky to Illinois

Explore weekly flight availability from Kentucky to Illinois. 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 September 17, 2025.

The most flights from USKY to USIL are scheduled on a Monday (42 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (33 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest, United Airlines, and American Airlines. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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
7.2
Good
36 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Food

7.0

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 Kentucky to Illinois. 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 Kentucky to Illinois?

    Departing from Kentucky to Illinois will take you 1h 35m. The distance between Kentucky and Illinois is about 395 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Kentucky to Illinois one-way?

    One-way options have recently been found by users for as low as $49 on United Airlines. Other airlines that offer cheap prices include Southwest from $49 and Allegiant Air from $55 one-way.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $245). Flying from Kentucky to Illinois in March is currently the most expensive (average of $321). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Kentucky to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Kentucky to Illinois

Discover the top 4 airlines that operate flights from Kentucky to Illinois. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$264FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$260FlexibilityNo cancel feeOn-time63%
ContourCheapest$113Average$144FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$123Average$320FlexibilityNo cancel feeOn-time69%

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