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Cheap flights from Chicago to Kentucky from $64

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 2/28. 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.
Frontier Logo
5:05 am - 5:32 pm
ORD
-
CVG
11h 27m
1 stop
Frontier Logo
1:07 pm - 10:30 am
CVG
-
ORD
22h 23m
1 stop
$150Frontier
Thu, Feb 12 - Mon, Feb 16
Frontier Logo
3:00 pm - 12:59 am
MDW
-
CVG
8h 59m
1 stop
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
$152Frontier
Thu, Feb 19 - Mon, Feb 23
American Airlines Logo
6:20 pm - 8:41 pm
ORD
-
CVG
1h 21mnonstop
American Airlines Logo
9:58 am - 10:30 am
CVG
-
ORD
1h 32mnonstop
$158American Airlines
Tue, Feb 17 - Wed, Feb 18
Allegiant Air Logo
2:48 pm - 5:18 pm
MDW
-
TYS
1h 30mnonstop
Allegiant Air Logo
1:22 pm - 1:58 pm
TYS
-
MDW
1h 36mnonstop
$160Allegiant Air
Thu, Jul 16 - Sun, Jul 19
Frontier Logo
6:15 am - 4:37 pm
MDW
-
CVG
9h 22m
1 stop
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
$160Frontier
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
5:55 pm - 8:13 pm
ORD
-
CVG
1h 18mnonstop
United Airlines Logo
4:25 pm - 5:00 pm
CVG
-
ORD
1h 35mnonstop
$164United Airlines
Sat, Mar 7 - Wed, Mar 11
American Airlines Logo
3:05 pm - 5:25 pm
ORD
-
CVG
1h 20mnonstop
American Airlines Logo
12:54 pm - 1:28 pm
CVG
-
ORD
1h 34mnonstop
$166American Airlines
Wed, Feb 18 - Thu, Feb 19
United Airlines Logo
1:01 pm - 3:28 pm
ORD
-
CVG
1h 27mnonstop
United Airlines Logo
7:00 am - 7:32 am
CVG
-
ORD
1h 32mnonstop
$171United Airlines
Thu, Feb 19 - Thu, Feb 26
Southwest Logo
6:05 pm - 8:15 pm
MDW
-
CVG
1h 10mnonstop
Southwest Logo
6:35 am - 6:55 am
CVG
-
MDW
1h 20mnonstop
$171Southwest
Thu, Feb 19 - Mon, Feb 23
Southwest Logo
6:05 pm - 8:15 pm
MDW
-
CVG
1h 10mnonstop
Southwest Logo
3:50 pm - 9:25 pm
CVG
-
MDW
6h 35m
1 stop
$181Southwest
Thu, Feb 19 - Mon, Feb 23

Spirit Airlines flights from Chicago to Kentucky

Our best Spirit Airlines deals on Chicago to Kentucky flight tickets
Spirit Airlines
Feb 16
ORD6:51 pmChicago O'Hare Intl
24h 57m
2 stops
BNA7:48 pmNashville Intl
Feb 23
BNA8:52 pmNashville Intl
14h 30m
1 stop
ORD11:22 amChicago O'Hare Intl
$184
Spirit Airlines
Feb 16
ORD10:44 amChicago O'Hare Intl
20h 41m
2 stops
BNA7:25 amNashville Intl
Feb 23
BNA8:52 pmNashville Intl
14h 30m
1 stop
ORD11:22 amChicago O'Hare Intl
$186
Spirit Airlines
Feb 6
ORD8:43 pmChicago O'Hare Intl
10h 42m
1 stop
BNA7:25 amNashville Intl
Feb 10
BNA8:12 pmNashville Intl
15h 10m
1 stop
ORD11:22 amChicago O'Hare Intl
$187

Frontier flights from Chicago to Kentucky

Our best Frontier deals on Chicago to Kentucky flight tickets
Frontier
Feb 12
ORD5:05 amChicago O'Hare Intl
11h 27m
1 stop
CVG5:32 pmCincinnati Cinci./N. Kentucky
Feb 16
CVG1:07 pmCincinnati Cinci./N. Kentucky
22h 23m
1 stop
ORD10:30 amChicago O'Hare Intl
$150
Frontier
Feb 19
MDW3:00 pmChicago Midway
8h 59m
1 stop
CVG12:59 amCincinnati Cinci./N. Kentucky
Feb 23
CVG1:07 pmCincinnati Cinci./N. Kentucky
7h 40m
1 stop
MDW7:47 pmChicago Midway
$152
Frontier
Feb 19
MDW6:15 amChicago Midway
9h 22m
1 stop
CVG4:37 pmCincinnati Cinci./N. Kentucky
Feb 23
CVG1:07 pmCincinnati Cinci./N. Kentucky
7h 40m
1 stop
MDW7:47 pmChicago Midway
$160

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 January 21, 2026.
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

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/12

5:05 am-5:32 pm

1 stop11h 27m

Cincinnati Cinci./N. Kentucky

Mon 2/16

1:07 pm-10:30 am

1 stop22h 23m

$150

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

3:00 pm-12:59 am

1 stop8h 59m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

$152

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 2/17

6:20 pm-8:41 pm

Nonstop1h 21m

Cincinnati Cinci./N. Kentucky

Wed 2/18

9:58 am-10:30 am

Nonstop1h 32m

$158

ChicagoKnoxville

MDW - TYS

MDWTYS

Chicago Midway

Thu 7/16

2:48 pm-5:18 pm

Nonstop1h 30m

Knoxville McGhee Tyson

Sun 7/19

1:22 pm-1:58 pm

Nonstop1h 36m

$160

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

6:15 am-4:37 pm

1 stop9h 22m

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

$160

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Sat 3/7

5:55 pm-8:13 pm

Nonstop1h 18m

Cincinnati Cinci./N. Kentucky

Wed 3/11

4:25 pm-5:00 pm

Nonstop1h 35m

$164

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 2/18

3:05 pm-5:25 pm

Nonstop1h 20m

Cincinnati Cinci./N. Kentucky

Thu 2/19

12:54 pm-1:28 pm

Nonstop1h 34m

$166

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 2/19

1:01 pm-3:28 pm

Nonstop1h 27m

Cincinnati Cinci./N. Kentucky

Thu 2/26

7:00 am-7:32 am

Nonstop1h 32m

$171

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

6:05 pm-8:15 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Mon 2/23

6:35 am-6:55 am

Nonstop1h 20m

$171

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Thu 2/19

6:05 pm-8:15 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Mon 2/23

3:50 pm-9:25 pm

1 stop6h 35m

$181

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 September is your next best option. Flight prices from Chicago to Kentucky during September average around $225.

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 Sunday because tickets tend to average around $423. 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 $308.

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 $306 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 $129 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

$55

Fastest flight time

1h 05m

Direct flights

Every day

Airports in Kentucky

43 airports
The best one-way flight to Kentucky from Chicago in the past 72 hours is $55. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $108.
The fastest flight from Chicago to Kentucky takes 1h 05m
Direct flights go from Chicago to Kentucky every day.
There are 43 airports in Kentucky. From Chicago there are direct flights to 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
8.0
4,266 reviews
Search Southwest flights
ContourPriceFrom $126Free CancellationRating
7.6
42 reviews
Search Contour flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
9,191 reviews
Search United Airlines flights
American AirlinesPriceFrom $136Free CancellationRating
7.2
11,174 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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