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$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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — CHI
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
1 adult, Economy
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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 May 27, 2026.

This Southwest deal was found by Cheapflights users on 5/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:40 pm
CVG
-
MDW
Nonstop1h 10m
Southwest
Wed 6/246:15 pm
MDW
-
CVG
Nonstop1h 10m
Southwest
Deal found 5/25$192
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:00 am
CVG
-
MDW
2 stops7h 35m
Southwest
Wed 6/1711:25 am
MDW
-
CVG
2 stops9h 25m
Southwest
Deal found 5/26$193
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/264:10 pm
CVG
-
ORD
1 stop5h 17m
Delta
Mon 8/316:51 am
ORD
-
CVG
1 stop5h 51m
Delta
Deal found 5/26$194
This Southwest deal was found by Cheapflights users on 5/22. 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.
Mon 8/177:00 pm
CVG
-
MDW
Nonstop1h 10m
Southwest
Thu 8/206:10 pm
MDW
-
CVG
Nonstop1h 15m
Southwest
Deal found 5/22$195
This American Airlines deal was found by Cheapflights users on 5/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/86:00 am
CVG
-
ORD
Nonstop1h 36m
American Airlines
Mon 8/106:58 am
ORD
-
CVG
Nonstop1h 25m
American Airlines
Deal found 5/22$195
This Delta deal was found by Cheapflights users on 5/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/102:23 pm
CVG
-
ORD
1 stop5h 05m
Delta
Tue 8/188:48 am
ORD
-
CVG
1 stop3h 54m
Delta
Deal found 5/26$196
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:10 pm
CVG
-
MDW
1 stop5h 15m
Delta
Tue 8/49:24 am
MDW
-
CVG
1 stop3h 18m
Delta
Deal found 5/25$197
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:25 am
CVG
-
ORD
1 stop5h 12m
Delta
Tue 7/288:52 am
ORD
-
CVG
1 stop3h 38m
Delta
Deal found 5/25$197
This Southwest deal was found by Cheapflights users on 5/22. 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.
Sat 9/52:50 pm
CVG
-
MDW
1 stop6h 30m
Southwest
Mon 9/76:10 pm
MDW
-
CVG
Nonstop1h 15m
Southwest
Deal found 5/22$201
This Southwest deal was found by Cheapflights users on 5/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:35 pm
CVG
-
MDW
1 stop5h 40m
Southwest
Tue 7/2811:25 am
MDW
-
CVG
2 stops9h 30m
Southwest
Deal found 5/25$202
This Delta deal was found by Cheapflights users on 5/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:23 pm
CVG
-
ORD
1 stop5h 05m
Delta
Wed 8/198:48 am
ORD
-
CVG
1 stop3h 54m
Delta
Deal found 5/25$204
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/107:05 am
CVG
-
MDW
2 stops6h 10m
Southwest
Tue 8/182:00 pm
MDW
-
CVG
2 stops5h 50m
Southwest
Deal found 5/26$206

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 May 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$192
(Southwest)

One-way from

$79
(Southwest)

Popular in

January

Cheapest in

November

Average price

$380

Good round-trip deal

$118 or less

Good one-way deal

$203 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. 11% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 May 27, 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

Tue 7/21

6:35 pm-11:15 pm

1 stop5h 40m

Chicago Midway

Tue 7/28

11:25 am-9:55 pm

2 stops9h 30m

$202

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 8/10

7:05 am-12:15 pm

2 stops6h 10m

Chicago Midway

Tue 8/18

2:00 pm-8:50 pm

2 stops5h 50m

$206

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/12

5:50 am-10:40 am

1 stop5h 50m

Chicago Midway

Mon 9/14

2:35 pm-10:20 pm

2 stops6h 45m

$216

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 8/17

5:25 pm-10:20 pm

1 stop5h 55m

Chicago Midway

Thu 8/20

2:35 pm-10:20 pm

2 stops6h 45m

$220
Quickest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 7/8

7:40 pm-7:50 pm

Nonstop1h 10m

Chicago Midway

Sat 7/11

5:45 pm-8:00 pm

Nonstop1h 15m

$225

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 8/26

10:50 am-5:20 pm

1 stop6h 30m

Chicago O'Hare Intl

Fri 8/28

9:39 am-5:05 pm

1 stop7h 26m

$233

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 7/14

7:00 am-11:00 am

1 stop5h 00m

Chicago Midway

Fri 7/17

1:00 pm-3:10 pm

Nonstop1h 10m

$239

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Wed 6/17

7:00 am-7:28 am

Nonstop1h 28m

Chicago O'Hare Intl

Sun 6/21

12:46 pm-3:16 pm

Nonstop1h 30m

$243

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 7/29

6:25 am-9:08 am

1 stop3h 43m

Chicago Midway

Sat 8/1

6:35 pm-10:47 pm

1 stop3h 12m

$245

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 7/28

2:10 pm-6:25 pm

1 stop5h 15m

Chicago Midway

Sat 8/1

6:35 pm-10:47 pm

1 stop3h 12m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $58). Flying from Kentucky to Chicago in February is currently the most expensive (average of $118). 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 May 27, 2026.

One of the essential ways to save on airfare from Kentucky to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 32% 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 May 27, 2026.

The most flights from USKY to CHI are scheduled on a Tuesday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (26 on average).

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

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 68 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 May 23, 2026.

Travelers seeking maximum savings on their Kentucky to Chicago flight should consider departing on Saturday at noon 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 30m. Fly via Southwest, United Airlines, or JetBlue 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 Contour, which is currently one of the cheapest options available, starting at $43. United Airlines flights start at $53 while deals on American 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 Knoxville McGhee Tyson - 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: Republic Airways (82%), British Airways (82%), Finnair( 81%).

  • What are the cheapest flights from Kentucky to Chicago?

    On average you can expect to pay $1,192 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 $202.

  • 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, April is the cheapest month in which you can book a flight from Kentucky to Chicago (average of $58). Flying from Kentucky to Chicago in February is currently the most expensive (average of $118). 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
Hammond
Porter

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Alternative routes for Kentucky to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Orlando to Midway 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 May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$77Average$231FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$97Average$275FlexibilityNo cancel feeOn-time71%
ContourCheapest$108Average$170FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$288FlexibilityNo cancel feeOn-time69%

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