HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$79+ Cheap flights from Kentucky to Chicago (CHI)

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 9/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Kentucky to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Kentucky to Chicago

Cheapest flights from Kentucky to Chicago
Explore the most affordable flight options available from Kentucky to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 23, 2026.

This Southwest deal was found by Cheapflights users on 7/21. 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 8/123:30 pm
CVG
-
MDW
1 stop6h 15m
Southwest
Sat 8/155:55 am
MDW
-
CVG
1 stop5h 45m
Southwest
Deal found 7/21$177
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
CVG
-
MDW
2 stops10h 50m
Southwest
Mon 9/78:05 am
MDW
-
CVG
Nonstop1h 20m
Southwest
Deal found 7/22$178
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/2612:26 pm
CVG
-
ORD
1 stop20h 27m
Frontier
Sat 8/291:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/20$180
This Southwest deal was found by Cheapflights users on 7/18. 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.
Sat 9/56:40 am
CVG
-
MDW
2 stops7h 40m
Southwest
Sun 9/68:55 am
MDW
-
CVG
1 stop4h 05m
Southwest
Deal found 7/18$182
This Southwest deal was found by Cheapflights users on 7/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:05 am
CVG
-
MDW
2 stops9h 20m
Southwest
Mon 9/148:05 am
MDW
-
CVG
Nonstop1h 20m
Southwest
Deal found 7/22$183
This Kiwi.com deal was found by Cheapflights users on 7/20. 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 8/2112:26 pm
CVG
-
ORD
1 stop20h 27m
Multiple Airlines
Mon 8/248:05 am
ORD
-
CVG
2 stops10h 37m
Multiple Airlines
Deal found 7/20$183
This Kiwi.com deal was found by Cheapflights users on 7/20. 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.
Sun 8/3012:26 pm
CVG
-
ORD
1 stop20h 27m
Frontier
Mon 8/311:59 pm
ORD
-
CVG
1 stop20h 22m
Frontier
Deal found 7/20$184
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 9/1812:48 pm
CVG
-
ORD
1 stop7h 56m
Frontier
Sat 10/172:46 pm
ORD
-
CVG
2 stops19h 57m
Frontier
Deal found 7/19$185
This Southwest deal was found by Cheapflights users on 7/19. 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.
Sat 9/52:50 pm
CVG
-
MDW
1 stop6h 40m
Southwest
Mon 9/78:05 am
MDW
-
CVG
Nonstop1h 20m
Southwest
Deal found 7/19$186
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Mon 8/3110:09 am
CVG
-
ORD
2 stops27h 41m
Multiple Airlines
Fri 9/117:45 am
ORD
-
CVG
1 stop28h 29m
Multiple Airlines
Deal found 7/22$186
This Southwest deal was found by Cheapflights users on 7/21. 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.
Mon 8/247:05 am
CVG
-
MDW
2 stops6h 10m
Southwest
Wed 8/261:00 pm
MDW
-
CVG
2 stops6h 50m
Southwest
Deal found 7/21$187
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:10 pm
CVG
-
ORD
1 stop3h 19m
Delta
Sat 8/296:59 am
ORD
-
CVG
1 stop5h 43m
Delta
Deal found 7/21$187

Find flight deals from Kentucky to Chicago

Keep the following information in mind while searching for Kentucky to Chicago flight deals. Data was last updated July 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$177
(Southwest)

One-way from

$79
(Southwest)

Popular in

January

Cheapest in

November

Average price

$337

Good round-trip deal

$163 or less

Good one-way deal

$229 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 Chicago (CHI)
Search Deals
One-way flight from Kentucky to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Kentucky to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Kentucky to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Kentucky to Chicago 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 July 23, 2026.
Use the filters below to find and compare flights from Kentucky to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 8/19

5:30 pm-10:20 pm

1 stop5h 50m

Chicago Midway

Sat 8/22

2:25 pm-6:50 pm

1 stop3h 25m

$177

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/5

6:40 am-1:20 pm

2 stops7h 40m

Chicago Midway

Sun 9/6

8:55 am-2:00 pm

1 stop4h 05m

$182

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 8/22

2:50 pm-8:30 pm

1 stop6h 40m

Chicago Midway

Wed 8/26

10:10 am-8:50 pm

2 stops9h 40m

$182

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 8/10

7:54 pm-8:34 pm

Nonstop1h 40m

Chicago O'Hare Intl

Wed 8/12

6:50 am-9:16 am

Nonstop1h 26m

$195
Quickest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 8/11

9:05 am-9:10 am

Nonstop1h 05m

Chicago Midway

Wed 8/12

5:55 pm-8:10 pm

Nonstop1h 15m

$195

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 9/11

2:10 pm-6:15 pm

1 stop5h 05m

Chicago Midway

Mon 9/14

2:35 pm-10:20 pm

2 stops6h 45m

$201

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 10/6

7:30 pm-7:45 pm

Nonstop1h 15m

Chicago Midway

Wed 10/14

9:30 am-2:50 pm

1 stop4h 20m

$205

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 8/20

6:00 am-12:20 pm

2 stops7h 20m

Chicago Midway

Thu 8/27

2:35 pm-10:20 pm

2 stops6h 45m

$206

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 8/29

8:14 am-12:39 pm

1 stop5h 25m

Chicago Midway

Mon 8/31

5:45 pm-10:40 pm

1 stop3h 55m

$215

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Fri 8/21

2:23 pm-6:29 pm

1 stop5h 06m

Chicago O'Hare Intl

Sat 8/22

2:30 pm-7:54 pm

1 stop4h 24m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Kentucky to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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 Chicago

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

Currently, October is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $227). Flying from Kentucky to Chicago in June is currently the most expensive (average of $367). 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 CHI?

Find hourly flight availability from Kentucky to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 23, 2026.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the morning could potentially save you up to 34% on airfare.

Weekly flight availability from Kentucky to Chicago

Explore weekly flight availability from Kentucky to Chicago. 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 July 23, 2026.

The most flights from USKY to CHI are scheduled on a Wednesday (41 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (20 on average).

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

Airfare is below average for this route at the moment.
Kentucky to Chicago flights typically cost between $275 and $402 in August.
The cheapest round-trip price found within the last 5 days was $217 on United Airlines (Aug 15-Aug 18).

How far ahead should I book a flight from Kentucky to Chicago?

To ensure you get the cheapest price possible for a flight from Kentucky to Chicago, you should look to book at least 78 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Use this chart to determine the cheapest time to fly round-trip from Kentucky to Chicago. Price data was last updated on July 18, 2026.

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

Related info for your journey

Find useful and relevant information for your journey from Kentucky to Chicago. 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 Chicago?

    There are many flights that can get you from Kentucky to Chicago in 1h 40m. Fly via Southwest, United Airlines, or Delta to get the fastest option. The distance from Kentucky to Chicago is about 265 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $38. Contour flights start at $44 while deals on United Airlines start at $53 one-way.

  • What are the most popular routes from Kentucky to Chicago?

    The most popular flight routes from Kentucky to Chicago are Nashville Intl - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl and Louisville Intl - Chicago O'Hare Intl.

  • What are the most reliable airlines from Kentucky to Chicago?

    Before booking your flight to Chicago from Kentucky, check out the most reliable airlines to get you to your destination on time: Japan Airlines (91%), Qatar Airways (87%), Republic Airways( 86%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $3,657 for a flight from Kentucky to Chicago. The cheapest flight overall is $148 while the most popular route, (Nashville Intl - Chicago O'Hare Intl) is currently priced at $217.

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

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

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

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

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

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

    Currently, October is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $227). Flying from Kentucky to Chicago in June is currently the most expensive (average of $367). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to Midway flights
Baltimore to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Ontario to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
San Francisco to O'Hare Intl flights
Denver to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Tampa to O'Hare Intl flights
Orlando to O'Hare Intl flights
Atlanta to O'Hare Intl flights
LaGuardia to Midway flights
Fort Lauderdale to O'Hare Intl flights
Hobby to O'Hare Intl flights
Austin to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to Midway flights
George Bush Intcntl to O'Hare Intl flights
Miami to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Los Angeles to Midway flights
Atlanta to Midway flights
Minneapolis to Midway flights
Minneapolis to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Hobby to Midway flights
Seattle to Midway flights
San Diego to O'Hare Intl flights
Newark to St. Louis flights
Portland to O'Hare Intl flights
Philadelphia to Midway flights
San Francisco to Midway flights
Cleveland to O'Hare Intl flights
Salt Lake City to O'Hare Intl flights
LaGuardia to St. Louis flights
San Jose to O'Hare Intl flights
Boston to Midway flights
Hartford to O'Hare Intl flights
Burbank to O'Hare Intl flights

Top 4 airlines flying from Kentucky to Chicago

Discover the top 4 airlines that operate flights from Kentucky to Chicago. 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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$77Average$269FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$97Average$288FlexibilityNo cancel feeOn-time71%
ContourCheapest$104Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$287FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.