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Cheap flights from Chicago to Kentucky from $47

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 11/13. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Kentucky

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:55 pm - 9:18 pmORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 23mnonstop
American Airlines Logo
6:00 am - 6:36 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 36mnonstop
$157American Airlines
Sat, Sep 5 - Sun, Sep 6
United Airlines Logo
9:00 am - 11:26 amORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 26mnonstop
United Airlines Logo
6:26 pm - 7:00 pmCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 34mnonstop
$157United Airlines
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
8:00 am - 10:25 amMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
1h 25mnonstop
Southwest Logo
7:30 pm - 7:40 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
1h 10mnonstop
$157Southwest
Sat, Sep 5 - Sun, Sep 6
Southwest Logo
3:25 pm - 5:40 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
1h 15mnonstop
Southwest Logo
7:30 pm - 7:40 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
1h 10mnonstop
$157Southwest
Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
6:55 pm - 9:18 pmORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 23mnonstop
American Airlines Logo
6:00 am - 6:36 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 36mnonstop
$158American Airlines
Sat, Sep 5 - Sun, Sep 6
Delta Logo
6:59 am - 1:42 pmORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
5h 43m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 10:42 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
5h 32m1 stop Detroit Metropolitan Wayne County
$177Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
5:45 pm - 10:40 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
3h 55m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:10 am - 9:17 amCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
$177Delta
Sat, Sep 5 - Sun, Sep 6
Frontier Logo
1:02 pm - 11:59 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
9h 57m1 stop Dallas/Fort Worth
Frontier Logo
12:48 pm - 9:58 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
$180Frontier
Sat, Oct 10 - Mon, Oct 12
United Airlines Logo
12:50 pm - 3:21 pmORD  Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky
1h 31mnonstop
United Airlines Logo
7:00 am - 7:38 amCVG  Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl
1h 38mnonstop
$181United Airlines
Sat, Sep 5 - Sat, Sep 12
Frontier Logo
1:02 pm - 11:59 pmMDW  Chicago Midway-CVG Cincinnati Cinci./N. Kentucky
9h 57m1 stop Dallas/Fort Worth
Frontier Logo
12:48 pm - 9:58 pmCVG  Cincinnati Cinci./N. Kentucky-MDW Chicago Midway
10h 10m1 stop Atlanta Hartsfield-Jackson
$200Frontier
Sat, Oct 10 - Tue, Oct 13

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Contour flights from Chicago to Kentucky

Our best Contour deals on Chicago to Kentucky flight tickets
Contour
Aug 21
ORD12:30 pmChicago O'Hare Intl
3h 40m
1 stop
BNA4:10 pmNashville Intl
Aug 24
BNA8:00 amNashville Intl
3h 40m
1 stop
ORD11:40 amChicago O'Hare Intl
$208
Contour
Sep 3
ORD12:30 pmChicago O'Hare Intl
3h 40m
1 stop
BNA4:10 pmNashville Intl
Sep 7
BNA8:00 amNashville Intl
3h 40m
1 stop
ORD11:40 amChicago O'Hare Intl
$209
Contour
Sep 3
ORD12:30 pmChicago O'Hare Intl
3h 40m
1 stop
BNA4:10 pmNashville Intl
Sep 7
BNA8:00 amNashville Intl
3h 40m
1 stop
ORD11:40 amChicago O'Hare Intl
$212

American Airlines flights from Chicago to Kentucky

Our best American Airlines deals on Chicago to Kentucky flight tickets
American Airlines
Sep 5
ORD6:55 pmChicago O'Hare Intl
1h 23m
CVG9:18 pmCincinnati Cinci./N. Kentucky
Sep 6
CVG6:00 amCincinnati Cinci./N. Kentucky
1h 36m
ORD6:36 amChicago O'Hare Intl
$158
American Airlines
Sep 19
ORD6:30 pmChicago O'Hare Intl
1h 34m
CVG9:04 pmCincinnati Cinci./N. Kentucky
Sep 26
CVG5:34 amCincinnati Cinci./N. Kentucky
1h 43m
ORD6:17 amChicago O'Hare Intl
$206
American Airlines
Sep 4
ORD9:15 pmChicago O'Hare Intl
1h 31m
LEX11:46 pmLexington Blue Grass
Sep 7
LEX6:34 amLexington Blue Grass
1h 56m
ORD7:30 amChicago O'Hare Intl
$215

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 August 10, 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

Cheapest round-trip

ChicagoCincinnati

ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky

ORDCVG

Chicago O'Hare Intl

Sat 9/5

6:55 pm-9:18 pm

Nonstop1h 23m

Cincinnati Cinci./N. Kentucky

Sun 9/6

6:00 am-6:36 am

Nonstop1h 36m

$157

ChicagoCincinnati

ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky

ORDCVG

Chicago O'Hare Intl

Sat 9/5

9:00 am-11:26 am

Nonstop1h 26m

Cincinnati Cinci./N. Kentucky

Sun 9/6

6:26 pm-7:00 pm

Nonstop1h 34m

$157

ChicagoCincinnati

MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky

MDWCVG

Chicago Midway

Sat 9/5

8:00 am-10:25 am

Nonstop1h 25m

Cincinnati Cinci./N. Kentucky

Sun 9/6

7:30 pm-7:40 pm

Nonstop1h 10m

$157
Quickest round-trip

ChicagoCincinnati

MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky

MDWCVG

Chicago Midway

Sat 9/5

3:25 pm-5:40 pm

Nonstop1h 15m

Cincinnati Cinci./N. Kentucky

Sun 9/6

7:30 pm-7:40 pm

Nonstop1h 10m

$157

ChicagoCincinnati

ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky

ORDCVG

Chicago O'Hare Intl

Sat 9/5

6:55 pm-9:18 pm

Nonstop1h 23m

Cincinnati Cinci./N. Kentucky

Sun 9/6

6:00 am-6:36 am

Nonstop1h 36m

$158

ChicagoCincinnati

ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky

ORDCVG

Chicago O'Hare Intl

Sat 9/5

6:59 am-1:42 pm

1 stop5h 43m

Cincinnati Cinci./N. Kentucky

Sun 9/6

6:10 am-10:42 am

1 stop5h 32m

$177

ChicagoCincinnati

MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky

MDWCVG

Chicago Midway

Sat 9/5

5:45 pm-10:40 pm

1 stop3h 55m

Cincinnati Cinci./N. Kentucky

Sun 9/6

6:10 am-9:17 am

1 stop4h 07m

$177

ChicagoCincinnati

MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky

MDWCVG

Chicago Midway

Sat 10/10

1:02 pm-11:59 pm

1 stop9h 57m

Cincinnati Cinci./N. Kentucky

Mon 10/12

12:48 pm-9:58 pm

1 stop10h 10m

$180

ChicagoCincinnati

ORD Chicago O'Hare Intl - CVG Cincinnati Cinci./N. Kentucky

ORDCVG

Chicago O'Hare Intl

Sat 9/5

12:50 pm-3:21 pm

Nonstop1h 31m

Cincinnati Cinci./N. Kentucky

Sat 9/12

7:00 am-7:38 am

Nonstop1h 38m

$181

ChicagoCincinnati

MDW Chicago Midway - CVG Cincinnati Cinci./N. Kentucky

MDWCVG

Chicago Midway

Sat 10/10

1:02 pm-11:59 pm

1 stop9h 57m

Cincinnati Cinci./N. Kentucky

Tue 10/13

12:48 pm-9:58 pm

1 stop10h 10m

$200

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 December, then November is your next best option. Flight prices from Chicago to Kentucky during November average around $273.

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 $295. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $501. 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 morning. momondo users have found flights departing from Chicago to Kentucky in the morning for as low as $360. 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 in the afternoon when prices are around $486.

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 from Chicago 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 $389 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 $228 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

$134

Fastest flight time

1h 10m

Direct flights

Every day

Airports in Kentucky

43 airports
The best one-way flight to Kentucky from Chicago in the past 72 hours is $134. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $194.
The fastest flight from Chicago to Kentucky takes 1h 10m
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), Nashville Intl (BNA), Cincinnati Cinci./N. Kentucky (CVG).
Search flight deals

Frequently asked questions about flying from Chicago to Kentucky

  • 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
ContourPriceFrom $104Free CancellationRating
7.7
42 reviews
Search Contour flights
SouthwestPriceFrom $129Free CancellationRating
8.0
4,218 reviews
Search Southwest flights
United AirlinesPriceFrom $137Free CancellationRating
7.4
10,101 reviews
Search United Airlines flights
American AirlinesPriceFrom $139Free CancellationRating
7.1
11,904 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.

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