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Kentucky

$39+ Cheap flights from Chicago (CHI) to Kentucky

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 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SDF
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Chicago to Kentucky

Keep the following information in mind while searching for Chicago to Kentucky flight deals. Data was last updated August 14, 2025.

Round-trip from

$77
(United Airlines)

One-way from

$39
(United Airlines)

Popular in

February

Cheapest in

August

Average price

$173

Good round-trip deal

$151 or less

Good one-way deal

$38 or less
From Chicago (CHI) to Kentucky
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One-way flight from Chicago (CHI) to Kentucky
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Highest demand for flights based on searches. 16% potential increase in price ($60 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Kentucky.
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Price to beat on a one-way flight from Chicago (CHI) to Kentucky.
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Find flight deals from Chicago to Kentucky

Cheapest flights from Chicago to Kentucky
Explore the most affordable flight options available from Chicago to Kentucky. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This United Airlines deal was found by Cheapflights users on 8/12. 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.
Tue 9/97:44 pmORD - SDF
Nonstop1h 40mUnited Airlines
Tue 9/167:36 pmSDF - ORD
Nonstop1h 49mUnited Airlines
Deal found 8/12$77
This Southwest deal was found by Cheapflights users on 8/12. 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.
Tue 9/3010:05 amMDW - SDF
Nonstop1h 20mSouthwest
Sat 10/44:25 pmSDF - MDW
Nonstop1h 15mSouthwest
Deal found 8/12$77
This Frontier deal was found by Cheapflights users on 8/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:53 pmORD - BNA
Nonstop1h 43mFrontier
Mon 9/153:21 pmBNA - ORD
Nonstop2h 05mFrontier
Deal found 8/12$78
This Frontier deal was found by Cheapflights users on 8/12. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/412:53 pmORD - BNA
Nonstop1h 43mFrontier
Mon 9/83:21 pmBNA - ORD
Nonstop2h 05mFrontier
Deal found 8/12$79
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 11/64:01 pmORD - BNA
Nonstop1h 40mSpirit Airlines
Fri 11/76:46 pmBNA - ORD
Nonstop1h 45mSpirit Airlines
Deal found 8/13$81
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/611:57 amORD - BNA
1 stop10h 37mMultiple Airlines
Mon 9/83:21 pmBNA - ORD
Nonstop2h 05mMultiple Airlines
Deal found 8/13$82
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/134:01 pmORD - BNA
Nonstop1h 40mSpirit Airlines
Sun 11/166:46 pmBNA - ORD
Nonstop1h 45mSpirit Airlines
Deal found 8/12$83
This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/812:53 pmORD - BNA
Nonstop1h 43mMultiple Airlines
Sat 9/135:46 amBNA - ORD
1 stop11h 53mMultiple Airlines
Deal found 8/12$84
This Cheapflightsfares deal was found by Cheapflights users on 8/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1011:57 amORD - BNA
1 stop10h 37mSpirit Airlines
Wed 9/175:46 amBNA - ORD
1 stop11h 53mSpirit Airlines
Deal found 8/13$85
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/74:01 pmORD - BNA
Nonstop1h 40mSpirit Airlines
Mon 11/106:46 pmBNA - ORD
Nonstop1h 45mSpirit Airlines
Deal found 8/12$86
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/64:01 pmORD - BNA
Nonstop1h 40mSpirit Airlines
Sat 11/89:50 pmBNA - ORD
1 stop11h 33mSpirit Airlines
Deal found 8/11$87
This Southwest deal was found by Cheapflights users on 8/12. 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.
Thu 9/412:15 pmMDW - BNA
1 stop4h 40mSouthwest
Thu 9/49:15 pmBNA - MDW
Nonstop1h 35mSouthwest
Deal found 8/12$87

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Kentucky 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 August 14, 2025.
Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.

Fly from

Chicago

Fly to

Kentucky

Route

Depart

Return

Price

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 9/30

10:05 am-12:25 pm

Nonstop1h 20m

Louisville Intl

Sat 10/4

4:25 pm-4:40 pm

Nonstop1h 15m

$77

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 9/23

7:44 pm-10:24 pm

Nonstop1h 40m

Louisville Intl

Wed 9/24

7:36 pm-8:25 pm

Nonstop1h 49m

$77

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 9/9

7:44 pm-10:24 pm

Nonstop1h 40m

Louisville Intl

Tue 9/16

7:36 pm-8:25 pm

Nonstop1h 49m

$77

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 11/9

1:52 pm-3:35 pm

Nonstop1h 43m

Nashville Intl

Mon 11/10

4:20 pm-6:15 pm

Nonstop1h 55m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Fri 11/7

4:01 pm-5:41 pm

Nonstop1h 40m

Nashville Intl

Sun 11/9

6:46 pm-8:31 pm

Nonstop1h 45m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 9/8

12:53 pm-2:36 pm

Nonstop1h 43m

Nashville Intl

Thu 9/11

3:21 pm-5:26 pm

Nonstop2h 05m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/9

1:26 pm-3:10 pm

Nonstop1h 44m

Nashville Intl

Sun 10/12

8:59 pm-10:46 pm

Nonstop1h 47m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 11/3

1:52 pm-3:35 pm

Nonstop1h 43m

Nashville Intl

Mon 11/10

4:20 pm-6:15 pm

Nonstop1h 55m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 9/8

12:53 pm-2:36 pm

Nonstop1h 43m

Nashville Intl

Mon 9/15

3:21 pm-5:26 pm

Nonstop2h 05m

$78

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 11/3

1:52 pm-3:35 pm

Nonstop1h 43m

Nashville Intl

Thu 11/13

4:20 pm-6:15 pm

Nonstop1h 55m

$78

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Kentucky

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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 CHI to KY?

Find hourly flight availability from Chicago to Kentucky. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Chicago to Kentucky, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Chicago to Kentucky

Explore weekly flight availability from Chicago to Kentucky. 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 August 14, 2025.

The most flights from CHI to USKY are scheduled on a Thursday (43 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 on average).

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

Reviews of airlines servicing Kentucky

Get insights into the airlines that provide service to Kentucky. 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 Kentucky. Reviews last updated August 14, 2025.
Read reviews from past customers who have flown Southwest, United Airlines, and American Airlines from Chicago to Kentucky. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Overall

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kentucky. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $39. However, be on the lookout for offers from Southwest and Frontier, as they are both options that can get you from Chicago to Kentucky for a low price.

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

    The most popular route from Chicago to Kentucky is Chicago O'Hare Intl - Nashville Intl. You may also consider Chicago O'Hare Intl - Knoxville McGhee Tyson or Chicago Midway - Nashville Intl.

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

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Kentucky on time: GoJet (85%), Japan Airlines (84%), Piedmont Airlines (83%).

  • What are the cheapest flights from Chicago to Kentucky?

    Looking at all options, your cheapest flight can be booked for $75. While the most popular route (Chicago O'Hare Intl - Nashville Intl) can be booked for $68 on average our data indicates $201 when flying from Chicago to Kentucky.

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

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

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

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

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

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kentucky (average of $299). Flying from Chicago to Kentucky in April is currently the most expensive (average of $369). 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 Chicago to Kentucky

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Chicago to Kentucky

Discover the top 4 airlines that operate flights from Chicago to Kentucky. 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
ContourCheapest$104Average$148FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$124Average$532FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$132Average$272FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$137Average$344FlexibilityNo cancel feeOn-time69%

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