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Illinois

$49+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:50 am
BNA
-
STL
Nonstop1h 25m
Southwest
Wed 2/258:15 am
STL
-
BNA
1 stop4h 25m
Southwest
Deal found 1/28$107
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 2/231:07 pm
CVG
-
MDW
1 stop7h 40m
Frontier
Thu 2/266:15 am
MDW
-
CVG
1 stop9h 22m
Frontier
Deal found 1/28$148
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 2/231:07 pm
CVG
-
ORD
1 stop10h 32m
Frontier
Thu 2/2611:41 am
ORD
-
CVG
1 stop12h 18m
Frontier
Deal found 1/28$148
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:07 pm
CVG
-
ORD
1 stop22h 39m
Frontier
Wed 3/46:02 pm
ORD
-
CVG
1 stop22h 30m
Frontier
Deal found 1/28$149
This Frontier deal was found by Cheapflights users on 1/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/191:07 pm
CVG
-
ORD
1 stop10h 32m
Frontier
Mon 2/233:40 pm
ORD
-
CVG
1 stop8h 19m
Frontier
Deal found 1/27$150
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/161:07 pm
CVG
-
ORD
1 stop22h 23m
Frontier
Fri 2/205:05 am
ORD
-
CVG
1 stop11h 27m
Frontier
Deal found 1/28$154
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/52:35 pm
BNA
-
STL
1 stop4h 01m
Southern / Mokulele
Mon 2/99:50 am
STL
-
BNA
1 stop3h 58m
Southern / Mokulele
Deal found 1/28$155
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:00 am
CVG
-
MDW
Nonstop1h 25m
Southwest
Wed 3/111:20 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Deal found 1/28$157
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/257:00 am
CVG
-
ORD
Nonstop1h 32m
United Airlines
Wed 3/46:00 pm
ORD
-
CVG
Nonstop1h 18m
United Airlines
Deal found 1/28$157
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:22 pm
CVG
-
ORD
1 stop10h 24m
Frontier
Wed 2/116:02 pm
ORD
-
CVG
1 stop22h 30m
Frontier
Deal found 1/28$160
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:07 pm
CVG
-
ORD
1 stop22h 39m
Frontier
Tue 2/248:30 am
ORD
-
CVG
1 stop11h 55m
Frontier
Deal found 1/28$163
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 2/191:07 pm
CVG
-
MDW
1 stop10h 30m
Frontier
Mon 2/238:15 am
MDW
-
CVG
1 stop15h 44m
Frontier
Deal found 1/27$164

Find flight deals from Kentucky to Illinois

Keep the following information in mind while searching for Kentucky to Illinois flight deals. Data was last updated January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$107
(Southwest)

One-way from

$49
(Southwest)

Popular in

March

Cheapest in

November

Average price

$257

Good round-trip deal

$107 or less

Good one-way deal

$207 or less
Provider with most accurate pricing for Louisville Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Louisville Intl-Chicago (CHI) flights.
Search Deals
From Kentucky to Illinois
Search Deals
One-way flight from Kentucky to Illinois
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Illinois.
Search Deals
Price to beat on a one-way flight from Kentucky to Illinois.
Search Deals

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 January 29, 2026.
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

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Tue 2/24

8:50 am-10:15 am

Nonstop1h 25m

Lambert-St Louis

Wed 2/25

6:50 am-1:30 pm

2 stops6h 40m

$112

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Fri 2/20

1:07 pm-10:46 am

1 stop22h 39m

Chicago O'Hare Intl

Tue 2/24

8:30 am-9:25 pm

1 stop11h 55m

$163

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 5/14

7:00 am-7:32 am

Nonstop1h 32m

Chicago O'Hare Intl

Tue 5/19

12:50 pm-3:18 pm

Nonstop1h 28m

$164

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 4/16

8:30 am-9:06 am

Nonstop1h 36m

Chicago O'Hare Intl

Tue 4/21

1:00 pm-3:25 pm

Nonstop1h 25m

$164

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Tue 2/24

3:20 pm-10:51 am

2 stops20h 31m

Chicago O'Hare Intl

Sat 2/28

4:42 pm-11:33 pm

1 stop5h 51m

$166

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Wed 3/4

2:54 pm-10:27 pm

1 stop7h 33m

Lambert-St Louis

Fri 3/6

9:50 am-1:48 pm

1 stop3h 58m

$167

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 2/26

12:54 pm-1:28 pm

Nonstop1h 34m

Chicago O'Hare Intl

Thu 3/5

6:55 am-9:16 am

Nonstop1h 21m

$171

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 2/21

6:05 am-6:30 am

Nonstop1h 25m

Chicago Midway

Mon 2/23

6:05 pm-8:15 pm

Nonstop1h 10m

$171

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 2/23

7:45 pm-8:20 pm

Nonstop1h 35m

Chicago O'Hare Intl

Thu 2/26

9:25 pm-11:49 pm

Nonstop1h 24m

$171

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 4/16

10:10 am-10:46 am

Nonstop1h 36m

Chicago O'Hare Intl

Mon 4/20

9:30 pm-11:58 pm

Nonstop1h 28m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, September is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $77). Flying from Kentucky to Illinois in July is currently the most expensive (average of $139). 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 January 29, 2026.

A simple way to save on the total cost of your ticket is to fly from Kentucky to Illinois in the morning. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight at noon.

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

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Illinois. Price data was last updated on January 24, 2026.

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

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 January 29, 2026.

The most flights from USKY to USIL are scheduled on a Thursday (36 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 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 January 29, 2026.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest, Contour, and United 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
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Contour
7.6
Good
42 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,216 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,206 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 25m. The distance between Kentucky and Illinois is about 272 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 $38 on Southwest. Other airlines that offer cheap prices include American Airlines from $48 and United Airlines from $48 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, September is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $77). Flying from Kentucky to Illinois in July is currently the most expensive (average of $139). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$266FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$262FlexibilityNo cancel feeOn-time63%
ContourCheapest$108Average$163FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$114Average$273FlexibilityNo cancel feeOn-time69%

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