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$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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — ORD
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/10. 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.
Wed 12/39:00 pmBNA - ORD
Nonstop1h 50mSpirit Airlines
Sat 12/63:26 pmORD - BNA
1 stop7h 01mSpirit Airlines
Deal found 11/10$90
This United Airlines deal was found by Cheapflights users on 11/12. 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 12/249:05 amSDF - ORD
Nonstop1h 44mUnited Airlines
Wed 12/317:52 pmORD - SDF
Nonstop1h 38mUnited Airlines
Deal found 11/12$97
This Southwest deal was found by Cheapflights users on 11/12. 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 12/248:10 amBNA - MDW
Nonstop1h 45mSouthwest
Thu 12/256:35 amMDW - BNA
Nonstop1h 30mSouthwest
Deal found 11/12$97
This Southwest deal was found by Cheapflights users on 11/12. 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 12/248:10 amBNA - MDW
Nonstop1h 45mSouthwest
Wed 12/2412:15 pmMDW - BNA
1 stop4h 25mSouthwest
Deal found 11/12$107
This United Airlines deal was found by Cheapflights users on 11/11. 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 12/37:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
Tue 12/95:54 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 11/11$117
This Southwest deal was found by Cheapflights users on 11/12. 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 12/36:45 amSDF - MDW
Nonstop1h 15mSouthwest
Tue 12/98:50 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 11/12$117
This Southwest deal was found by Cheapflights users on 11/10. 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 12/38:55 pmBNA - MDW
Nonstop1h 40mSouthwest
Wed 12/176:20 pmMDW - BNA
Nonstop1h 35mSouthwest
Deal found 11/10$117
This United Airlines deal was found by Cheapflights users on 11/10. 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 12/1012:45 pmBNA - ORD
Nonstop1h 50mUnited Airlines
Wed 12/179:05 pmORD - BNA
Nonstop1h 44mUnited Airlines
Deal found 11/10$117
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Wed 12/36:30 amSDF - ORD
Nonstop1h 44mAmerican Airlines
Tue 12/98:20 pmORD - SDF
Nonstop1h 36mAmerican Airlines
Deal found 11/12$118
This Mytrip deal was found by Cheapflights users on 11/12. 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 12/39:00 pmBNA - ORD
Nonstop1h 50mSpirit Airlines
Mon 12/87:10 amORD - BNA
1 stop15h 17mSpirit Airlines
Deal found 11/12$121
This United Airlines deal was found by Cheapflights users on 11/12. 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 12/249:50 amBNA - ORD
Nonstop2h 04mUnited Airlines
Wed 12/245:50 pmORD - BNA
Nonstop1h 41mUnited Airlines
Deal found 11/12$125
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 11/258:45 amBNA - ORD
Nonstop1h 53mMultiple Airlines
Wed 12/33:43 pmORD - BNA
1 stop7h 59mMultiple Airlines
Deal found 11/11$126

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$90
(Kiwi.com)

One-way from

$49
(United Airlines)

Popular in

March

Cheapest in

November

Average price

$196

Good round-trip deal

$170 or less

Good one-way deal

$169 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
High demand for flights, 0% potential price rise
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 November 2025
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 November 13, 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

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 12/16

1:50 pm-2:28 pm

Nonstop1h 38m

Chicago O'Hare Intl

Wed 12/17

9:05 am-11:32 am

Nonstop1h 27m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 12/24

5:50 am-11:15 am

1 stop5h 25m

Chicago Midway

Wed 12/24

3:30 pm-7:55 pm

1 stop4h 25m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 12/10

11:05 am-12:45 pm

Nonstop1h 40m

Chicago Midway

Wed 12/17

5:35 am-7:05 am

Nonstop1h 30m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/3

4:48 pm-6:55 pm

Nonstop2h 07m

Chicago O'Hare Intl

Wed 12/17

2:00 pm-3:44 pm

Nonstop1h 44m

$117

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Wed 12/3

8:55 pm-10:35 pm

Nonstop1h 40m

Chicago Midway

Wed 12/17

6:20 pm-7:55 pm

Nonstop1h 35m

$117

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/24

9:50 am-11:54 am

Nonstop2h 04m

Chicago O'Hare Intl

Wed 12/24

5:50 pm-7:31 pm

Nonstop1h 41m

$125

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

1:50 pm-2:05 pm

Nonstop1h 15m

Chicago Midway

Tue 12/9

8:10 am-2:45 pm

1 stop5h 35m

$127

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 2/4

10:20 am-12:15 pm

Nonstop1h 55m

Chicago O'Hare Intl

Wed 2/4

2:15 pm-8:55 pm

1 stop6h 40m

$127

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sun 1/18

5:35 am-6:19 am

Nonstop1h 44m

Chicago O'Hare Intl

Mon 1/19

7:52 pm-10:30 pm

Nonstop1h 38m

$134

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/1

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Mon 1/5

2:40 pm-4:50 pm

Nonstop1h 10m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

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, January is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $73). 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 November 13, 2025.

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 11% 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 December 16, 2024.

Travelers seeking maximum savings on their Kentucky to Illinois flight should consider departing on Wednesday 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 November 13, 2025.

The most flights from USKY to USIL are scheduled on a Friday (39 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (34 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 November 13, 2025.
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
4,240 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
41 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
9,017 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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
11,051 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Food

7.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

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 38m. The distance between Kentucky and Illinois is about 287 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 Frontier 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, January is the cheapest month in which you can book a flight from Kentucky to Illinois (average of $73). 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$97Average$271FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$97Average$249FlexibilityNo cancel feeOn-time63%
ContourCheapest$116Average$155FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$123Average$313FlexibilityNo cancel feeOn-time69%

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