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Cheap flights from Chicago to Kentucky from $57

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kentucky departing on 1/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago to Kentucky

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
4:08 pm - 6:39 pm
ORD
-
SDF
1h 31mnonstop
American Airlines Logo
8:07 am - 9:00 am
SDF
-
ORD
1h 53mnonstop
$117American Airlines
Tue, Jan 6 - Tue, Jan 13
Frontier Logo
5:40 am - 11:55 am
ORD
-
CVG
5h 15m1 stop
Frontier Logo
1:22 pm - 10:46 pm
CVG
-
ORD
10h 24m1 stop
$128Frontier
Thu, Jan 22 - Mon, Jan 26
Southwest Logo
6:50 am - 1:35 pm
MDW
-
SDF
5h 45m1 stop
Southwest Logo
2:30 pm - 7:00 pm
SDF
-
MDW
5h 30m1 stop
$137Southwest
Tue, Jan 20 - Wed, Jan 21
Southwest Logo
6:10 am - 5:00 pm
MDW
-
SDF
9h 50m2 stops
Southwest Logo
12:50 pm - 7:00 pm
SDF
-
MDW
7h 10m1 stop
$142Southwest
Tue, Jan 20 - Wed, Jan 21
Multiple Airlines Logo
3:00 pm - 7:25 am
ORD
-
BNA
16h 25m1 stop
Multiple Airlines Logo
9:25 am - 4:19 pm
BNA
-
ORD
6h 54m1 stop
$142Multiple Airlines
Sun, Feb 8 - Wed, Feb 11
Allegiant Air Logo
2:47 pm - 5:13 pm
MDW
-
TYS
1h 26mnonstop
Allegiant Air Logo
1:22 pm - 1:57 pm
TYS
-
MDW
1h 35mnonstop
$144Allegiant Air
Thu, May 28 - Sun, May 31
Southwest Logo
1:45 pm - 3:20 pm
ORD
-
BNA
1h 35mnonstop
Southwest Logo
10:20 am - 12:15 pm
BNA
-
ORD
1h 55mnonstop
$144Southwest
Sat, Jan 10 - Tue, Jan 13
Multiple Airlines Logo
9:23 am - 3:12 pm
ORD
-
CVG
28h 49m1 stop
Multiple Airlines Logo
8:30 am - 7:38 pm
CVG
-
ORD
12h 08m1 stop
$145Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
United Airlines Logo
6:20 pm - 9:04 pm
ORD
-
LEX
1h 44mnonstop
United Airlines Logo
8:35 am - 9:30 am
LEX
-
ORD
1h 55mnonstop
$189United Airlines
Mon, Jan 5 - Mon, Jan 12
United Airlines Logo
6:00 pm - 8:45 pm
ORD
-
TYS
1h 45mnonstop
United Airlines Logo
7:00 am - 7:55 am
TYS
-
ORD
1h 55mnonstop
$218United Airlines
Fri, May 1 - Mon, May 4

Southwest flights from Chicago to Kentucky

Our best Southwest deals on Chicago to Kentucky flight tickets
Southwest
Jan 20
MDW6:50 amChicago Midway
5h 45m
1 stop
SDF1:35 pmLouisville Intl
Jan 21
SDF2:30 pmLouisville Intl
5h 30m
1 stop
MDW7:00 pmChicago Midway
$137
Find similar
Southwest
Jan 20
MDW6:10 amChicago Midway
9h 50m
2 stops
SDF5:00 pmLouisville Intl
Jan 21
SDF12:50 pmLouisville Intl
7h 10m
1 stop
MDW7:00 pmChicago Midway
$142
Find similar
Southwest
Jan 10
ORD1:45 pmChicago O'Hare Intl
1h 35m
BNA3:20 pmNashville Intl
Jan 13
BNA10:20 amNashville Intl
1h 55m
ORD12:15 pmChicago O'Hare Intl
$144
Find similar

United Airlines flights from Chicago to Kentucky

Our best United Airlines deals on Chicago to Kentucky flight tickets
United Airlines
Jan 8
ORD7:40 amChicago O'Hare Intl
1h 50m
BNA9:30 amNashville Intl
Jan 12
BNA8:00 amNashville Intl
1h 55m
ORD9:55 amChicago O'Hare Intl
$171
Find similar
United Airlines
Jan 5
ORD6:20 pmChicago O'Hare Intl
1h 44m
LEX9:04 pmLexington Blue Grass
Jan 12
LEX8:35 amLexington Blue Grass
1h 55m
ORD9:30 amChicago O'Hare Intl
$189
Find similar
United Airlines
Jan 17
ORD5:52 pmChicago O'Hare Intl
1h 41m
BNA7:33 pmNashville Intl
Jan 18
BNA8:00 amNashville Intl
1h 55m
ORD9:55 amChicago O'Hare Intl
$193
Find similar

momondo 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, momondo users made 832,500 searches. Data last updated December 9, 2025.
Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Tue 1/6

4:08 pm-6:39 pm

Nonstop1h 31m

Louisville Intl

Tue 1/13

8:07 am-9:00 am

Nonstop1h 53m

$117

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 1/22

5:40 am-11:55 am

1 stop5h 15m

Cincinnati Cinci./N. Kentucky

Mon 1/26

1:22 pm-10:46 pm

1 stop10h 24m

$128

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 1/20

6:50 am-1:35 pm

1 stop5h 45m

Louisville Intl

Wed 1/21

2:30 pm-7:00 pm

1 stop5h 30m

$137

ChicagoLouisville

MDW - SDF

MDWSDF

Chicago Midway

Tue 1/20

6:10 am-5:00 pm

2 stops9h 50m

Louisville Intl

Wed 1/21

12:50 pm-7:00 pm

1 stop7h 10m

$142

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 2/8

3:00 pm-7:25 am

1 stop16h 25m

Nashville Intl

Wed 2/11

9:25 am-4:19 pm

1 stop6h 54m

$142

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 5/28

2:47 pm-5:13 pm

Nonstop1h 26m

Knoxville McGhee Tyson

Sun 5/31

1:22 pm-1:57 pm

Nonstop1h 35m

$144

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 1/10

1:45 pm-3:20 pm

Nonstop1h 35m

Nashville Intl

Tue 1/13

10:20 am-12:15 pm

Nonstop1h 55m

$144

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 1/21

9:23 am-3:12 pm

1 stop28h 49m

Cincinnati Cinci./N. Kentucky

Mon 1/26

8:30 am-7:38 pm

1 stop12h 08m

$145

ChicagoLexington

ORD - LEX

ORDLEX

Chicago O'Hare Intl

Mon 1/5

6:20 pm-9:04 pm

Nonstop1h 44m

Lexington Blue Grass

Mon 1/12

8:35 am-9:30 am

Nonstop1h 55m

$189

ChicagoKnoxville

ORD - TYS

ORDTYS

Chicago O'Hare Intl

Fri 5/1

6:00 pm-8:45 pm

Nonstop1h 45m

Knoxville McGhee Tyson

Mon 5/4

7:00 am-7:55 am

Nonstop1h 55m

$218

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Kentucky from

How to get the cheapest flight ticket from Chicago to Kentucky

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in August, then January is your next best option. Flight prices from Chicago to Kentucky during January average around $216.

What is the cheapest day to depart on your flight to Kentucky?

Our data shows that Saturday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $249. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $390. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.

What is the cheapest time of day to depart on your flight to Kentucky?

According to our data, the cheapest time of day to fly to Kentucky is in the evening. momondo users have found flights departing from Chicago to Kentucky in the evening for as low as $275. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Kentucky is at noon when prices are around $303.

What is the cheapest Chicago to Kentucky flight route?

Fly from Chicago O'Hare Intl to Owensboro Daviess County for the best Chicago - Kentucky flight prices

How far in advance should I book a flight to Kentucky?

You are more likely to see cheaper flights to Kentucky from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Kentucky for around $308 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kentucky from Chicago for as low as $186 on momondo.

What cabin class options are available on Chicago to Kentucky flights?

There are 4 cabin classes available to choose from on Chicago to Kentucky flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Kentucky flights?

No. A direct flight is the cheapest option for a flight between Chicago to Kentucky.

Cheap Chicago to Kentucky flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Kentucky

Best Price Found

$128

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Kentucky

2 airports
The best one-way flight to Kentucky from Chicago in the past 72 hours is $128. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $148.
The fastest flight from Chicago to Kentucky takes 1h 05m
Direct flights go from Chicago to Kentucky every day.
There are 2 airports near Kentucky: Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG)
Search flight deals

  • When did momondo last update prices for flights from Chicago to Kentucky?

    Prices for flights from Chicago to Kentucky were last updated today.

  • How many operators does momondo search for flights from Chicago to Kentucky?

  • How old do you have to be to fly from Chicago to Kentucky?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Kentucky.

  • What documentation or ID do you need to fly to Kentucky?

    The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago to Kentucky?

Best airlines flying from Chicago to Kentucky

Compare and see reviews for airlines that fly from Chicago to Kentucky with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $124Free CancellationRating
7.9
4,252 reviews
Search Southwest flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights
ContourPriceFrom $127Free CancellationRating
7.6
43 reviews
Search Contour flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
11,046 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kentucky?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Kentucky from Chicago.

Can I find flights from Chicago to Kentucky with flexible booking policies on momondo?

momondo does allow users to show only those flights to Kentucky from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to Kentucky?

Once all potential Chicago to Kentucky flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Kentucky right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Kentucky flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Kentucky trip

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