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Illinois

$68+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Απρ 25 — Μαϊ 21
Σαβ 4/25
Σαβ 5/2
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 Μάρτιος 26, 2026.

This Frontier deal was found by Cheapflights users on 3/22. 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.
Δευ 4/1311:06 am
BNA
-
STL
1 stop12h 19m
Frontier
Παρ 4/178:39 am
STL
-
BNA
1 stop10h 02m
Frontier
Deal found 3/22$140
This CheapOair deal was found by Cheapflights users on 3/22. 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.
Δευ 4/1311:06 am
BNA
-
STL
1 stop12h 19m
Frontier
Σαβ 4/188:17 pm
STL
-
BNA
1 stop21h 11m
Frontier
Deal found 3/22$151
This Trip.com deal was found by Cheapflights users on 3/24. 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.
Πεμ 4/92:35 pm
BNA
-
STL
1 stop4h 01m
Southern / Mokulele
Δευ 4/139:50 am
STL
-
BNA
1 stop3h 58m
Southern / Mokulele
Deal found 3/24$154
This CheapOair deal was found by Cheapflights users on 3/24. 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.
Τρι 4/142:35 pm
BNA
-
STL
1 stop4h 01m
Multiple Airlines
Παρ 4/174:59 pm
STL
-
BNA
1 stop23h 59m
Multiple Airlines
Deal found 3/24$164
This CheapOair deal was found by Cheapflights users on 3/23. 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.
Δευ 4/1311:06 am
BNA
-
STL
1 stop12h 19m
Multiple Airlines
Πεμ 4/169:50 am
STL
-
BNA
1 stop3h 58m
Multiple Airlines
Deal found 3/23$169
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Παρ 4/102:35 pm
BNA
-
STL
1 stop4h 01m
Southern / Mokulele
Πεμ 4/169:50 am
STL
-
BNA
1 stop3h 58m
Southern / Mokulele
Deal found 3/22$171
This Southern / Mokulele deal was found by Cheapflights users on 3/26. 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 Southern / Mokulele is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Δευ 5/112:35 pm
BNA
-
STL
1 stop4h 01m
Southern / Mokulele
Σαβ 5/169:50 am
STL
-
BNA
1 stop3h 58m
Southern / Mokulele
Deal found 3/26$172
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Πεμ 4/96:00 am
CVG
-
ORD
1 stop17h 50m
Frontier
Τετ 4/156:08 pm
ORD
-
CVG
1 stop22h 25m
Frontier
Deal found 3/24$174
This United Airlines deal was found by Cheapflights users on 3/25. 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.
Τετ 4/2210:10 am
CVG
-
ORD
Nonstop1h 36m
United Airlines
Τετ 4/296:05 pm
ORD
-
CVG
Nonstop1h 24m
United Airlines
Deal found 3/25$175
This Southwest deal was found by Cheapflights users on 3/23. 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.
Τρι 6/27:35 pm
CVG
-
MDW
Nonstop1h 15m
Southwest
Τετ 6/36:10 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Deal found 3/23$176
This United Airlines deal was found by Cheapflights users on 3/24. 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.
Τρι 4/219:07 am
SDF
-
ORD
Nonstop1h 40m
United Airlines
Τρι 4/286:45 am
ORD
-
SDF
Nonstop1h 25m
United Airlines
Deal found 3/24$177
This Expedia deal was found by Cheapflights users on 3/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Παρ 6/512:46 pm
CVG
-
MDW
1 stop10h 16m
Frontier
Δευ 6/86:00 am
MDW
-
CVG
1 stop4h 41m
Frontier
Deal found 3/26$180

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 Μάρτιος 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Frontier)

One-way from

$68
(Kiwi.com)

Popular in

January

Cheapest in

November

Average price

$286

Good round-trip deal

$104 or less

Good one-way deal

$175 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. 19% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 Μάρτιος 26, 2026.
Use the filters below to find and compare flights from Kentucky to Illinois that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Τρι 4/14

2:35 pm-6:36 pm

1 stop4h 01m

Lambert-St Louis

Παρ 4/17

8:39 am-6:41 pm

1 stop10h 02m

$164

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Κυρ 4/5

2:35 pm-6:36 pm

1 stop4h 01m

Lambert-St Louis

Πεμ 4/9

9:50 am-1:48 pm

1 stop3h 58m

$171

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Δευ 5/11

2:35 pm-6:36 pm

1 stop4h 01m

Lambert-St Louis

Σαβ 5/16

9:50 am-1:48 pm

1 stop3h 58m

$172

NashvilleSt. Louis

BNA - STL

BNASTL

Nashville Intl

Δευ 4/6

2:35 pm-6:36 pm

1 stop4h 01m

Lambert-St Louis

Τρι 4/7

9:50 am-1:48 pm

1 stop3h 58m

$172

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Τρι 4/21

8:15 am-5:05 pm

2 stops9h 50m

Chicago Midway

Τρι 4/28

9:10 am-7:40 pm

2 stops9h 30m

$192

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Παρ 6/5

2:22 pm-9:17 am

1 stop18h 55m

Chicago Greater Rockford

Κυρ 6/7

9:19 am-10:44 am

Nonstop1h 25m

$194

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Σαβ 6/27

9:37 am-10:37 am

1 stop25h 00m

Chicago Greater Rockford

Κυρ 7/5

9:19 am-10:47 am

Nonstop1h 28m

$194

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Τετ 4/22

5:50 pm-10:15 pm

1 stop5h 25m

Chicago Midway

Τετ 4/29

8:00 am-12:40 pm

1 stop3h 40m

$195

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Παρ 5/22

5:13 pm-9:21 am

1 stop16h 08m

Chicago Greater Rockford

Κυρ 5/24

9:21 am-10:49 am

Nonstop1h 28m

$203

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Σαβ 6/6

1:35 pm-7:25 pm

1 stop6h 50m

Chicago Midway

Τρι 6/9

11:50 am-8:20 pm

1 stop7h 30m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/22

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, April is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $58). Flying from Kentucky to Illinois in March is currently the most expensive (average of $180). 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 Μάρτιος 26, 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 34% 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 March 23, 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. Monday 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 Μάρτιος 26, 2026.

The most flights from USKY to USIL are scheduled on a Thursday (35 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (14 on average).

How much does it cost to fly round-trip from Kentucky to Illinois?

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 Μάρτιος 26, 2026.
Read through reviews of airlines operating flights from Kentucky to Illinois, such as Southwest,Contour, andUnited 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
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,331 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Contour
7.6
Good
42 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,493 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,502 reviews
Southwest
8.0
Very good
4,331 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 4h 01m. 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 United Airlines from $48 and Contour from $52 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, April is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $58). Flying from Kentucky to Illinois in March is currently the most expensive (average of $180). 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 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 Μάρτιος 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$265FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$247FlexibilityNo cancel feeOn-time63%
ContourCheapest$104Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$114Average$264FlexibilityNo cancel feeOn-time69%

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