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Cheap flights from Chicago to Kentucky from $99

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.
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$157Contour
Thu, Oct 8 - Mon, Oct 12
Contour Logo
11:30 am - 1:00 pmORD  Chicago O'Hare Intl-OWB Owensboro Daviess County
1h 30mnonstop
Contour Logo
9:00 am - 10:50 amOWB  Owensboro Daviess County-ORD Chicago O'Hare Intl
1h 50mnonstop
$158Contour
Wed, Oct 7 - Sun, Oct 11
United Airlines Logo
12:02 pm - 1:32 pmORD  Chicago O'Hare Intl-PAH Paducah Barkley Regional
1h 30mnonstop
United Airlines Logo
5:00 am - 6:28 amPAH  Paducah Barkley Regional-ORD Chicago O'Hare Intl
1h 28mnonstop
$194United Airlines
Fri, Oct 9 - Tue, Oct 13
United Airlines Logo
12:00 pm - 1:38 pmORD  Chicago O'Hare Intl-PAH Paducah Barkley Regional
1h 38mnonstop
United Airlines Logo
5:00 am - 6:52 amPAH  Paducah Barkley Regional-ORD Chicago O'Hare Intl
1h 52mnonstop
$194United Airlines
Wed, Jan 6 - Mon, Jan 18
American Airlines Logo
6:59 pm - 9:36 pmORD  Chicago O'Hare Intl-SDF Louisville Intl
1h 37mnonstop
American Airlines Logo
1:32 pm - 2:15 pmSDF  Louisville Intl-ORD Chicago O'Hare Intl
1h 43mnonstop
$197American Airlines
Sat, Nov 7 - Sat, Nov 14
American Airlines Logo
6:59 am - 9:32 amORD  Chicago O'Hare Intl-SDF Louisville Intl
1h 33mnonstop
American Airlines Logo
6:07 pm - 7:05 pmSDF  Louisville Intl-ORD Chicago O'Hare Intl
1h 58mnonstop
$197American Airlines
Tue, Oct 20 - Tue, Oct 20
Southwest Logo
8:05 am - 10:20 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
Southwest Logo
5:05 pm - 5:25 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
$197Southwest
Sat, Oct 24 - Sat, Oct 24
Southwest Logo
8:15 am - 10:30 amMDW  Chicago Midway-SDF Louisville Intl
1h 15mnonstop
Southwest Logo
2:05 pm - 2:25 pmSDF  Louisville Intl-MDW Chicago Midway
1h 20mnonstop
$197Southwest
Wed, Dec 9 - Thu, Dec 10
Delta Logo
6:04 am - 12:54 pmMDW  Chicago Midway-SDF Louisville Intl
5h 50m1 stop Atlanta Hartsfield-Jackson
Delta Logo
12:40 pm - 4:47 pmSDF  Louisville Intl-MDW Chicago Midway
5h 07m1 stop Minneapolis St Paul
$217Delta
Wed, Oct 21 - Mon, Oct 26
Delta Logo
5:31 pm - 10:51 pmMDW  Chicago Midway-SDF Louisville Intl
4h 20m1 stop Minneapolis St Paul
Delta Logo
2:36 pm - 6:00 pmSDF  Louisville Intl-MDW Chicago Midway
4h 24m1 stop Detroit Metropolitan Wayne County
$217Delta
Mon, Oct 12 - Tue, Oct 13

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Delta flights from Chicago to Kentucky

Our best Delta deals on Chicago to Kentucky flight tickets
Delta
Oct 12
MDW5:31 pmChicago Midway
4h 20m
1 stop
SDF10:51 pmLouisville Intl
Oct 13
SDF2:36 pmLouisville Intl
4h 24m
1 stop
MDW6:00 pmChicago Midway
$217
Delta
Oct 15
ORD8:29 amChicago O'Hare Intl
4h 24m
1 stop
SDF1:53 pmLouisville Intl
Oct 19
SDF5:38 pmLouisville Intl
3h 52m
1 stop
ORD8:30 pmChicago O'Hare Intl
$218
Delta
Nov 4
ORD5:05 pmChicago O'Hare Intl
4h 42m
1 stop
SDF10:47 pmLouisville Intl
Nov 5
SDF5:57 pmLouisville Intl
7h 00m
1 stop
ORD11:57 pmChicago O'Hare Intl
$234

Southwest flights from Chicago to Kentucky

Our best Southwest deals on Chicago to Kentucky flight tickets
Southwest
Oct 12
MDW7:55 amChicago Midway
1h 15m
SDF10:10 amLouisville Intl
Oct 13
SDF2:05 pmLouisville Intl
1h 15m
MDW2:20 pmChicago Midway
$197
Southwest
Oct 12
MDW7:55 amChicago Midway
1h 15m
SDF10:10 amLouisville Intl
Oct 13
SDF3:55 pmLouisville Intl
6h 30m
1 stop
MDW9:25 pmChicago Midway
$207
Southwest
Nov 5
MDW7:45 amChicago Midway
1h 20m
SDF10:05 amLouisville Intl
Nov 10
SDF7:20 amLouisville Intl
8h 10m
2 stops
MDW2:30 pmChicago Midway
$212

momondo Fare Finder

 
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

ChicagoOwensboro

ORD Chicago O'Hare Intl - OWB Owensboro Daviess County

ORDOWB

Chicago O'Hare Intl

Thu 10/8

11:30 am-1:00 pm

Nonstop1h 30m

Owensboro Daviess County

Mon 10/12

9:00 am-10:50 am

Nonstop1h 50m

$157

ChicagoOwensboro

ORD Chicago O'Hare Intl - OWB Owensboro Daviess County

ORDOWB

Chicago O'Hare Intl

Wed 10/7

11:30 am-1:00 pm

Nonstop1h 30m

Owensboro Daviess County

Sun 10/11

9:00 am-10:50 am

Nonstop1h 50m

$158

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Fri 10/9

12:02 pm-1:32 pm

Nonstop1h 30m

Paducah Barkley Regional

Tue 10/13

5:00 am-6:28 am

Nonstop1h 28m

$194

ChicagoPaducah

ORD Chicago O'Hare Intl - PAH Paducah Barkley Regional

ORDPAH

Chicago O'Hare Intl

Wed 1/6

12:00 pm-1:38 pm

Nonstop1h 38m

Paducah Barkley Regional

Mon 1/18

5:00 am-6:52 am

Nonstop1h 52m

$194

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Sat 11/7

6:59 pm-9:36 pm

Nonstop1h 37m

Louisville Intl

Sat 11/14

1:32 pm-2:15 pm

Nonstop1h 43m

$197

ChicagoLouisville

ORD Chicago O'Hare Intl - SDF Louisville Intl

ORDSDF

Chicago O'Hare Intl

Tue 10/20

6:59 am-9:32 am

Nonstop1h 33m

Louisville Intl

Tue 10/20

6:07 pm-7:05 pm

Nonstop1h 58m

$197
Quickest round-trip

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Sat 10/24

8:05 am-10:20 am

Nonstop1h 15m

Louisville Intl

Sat 10/24

5:05 pm-5:25 pm

Nonstop1h 20m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Wed 12/9

8:15 am-10:30 am

Nonstop1h 15m

Louisville Intl

Thu 12/10

2:05 pm-2:25 pm

Nonstop1h 20m

$197

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Wed 10/21

6:04 am-12:54 pm

1 stop5h 50m

Louisville Intl

Mon 10/26

12:40 pm-4:47 pm

1 stop5h 07m

$217

ChicagoLouisville

MDW Chicago Midway - SDF Louisville Intl

MDWSDF

Chicago Midway

Mon 10/12

5:31 pm-10:51 pm

1 stop4h 20m

Louisville Intl

Tue 10/13

2:36 pm-6:00 pm

1 stop4h 24m

$217

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 $287.

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

Our data shows that Thursday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $325. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $499. 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 at noon. momondo users have found flights departing from Chicago to Kentucky at noon for as low as $385. 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 $489.

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 $402 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

$99

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 $99. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $157.
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), Paducah Barkley Regional (PAH), Owensboro Daviess County (OWB), Lexington Blue Grass (LEX).
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 $89Free CancellationRating
7.5
43 reviews
Search Contour flights
United AirlinesPriceFrom $143Free CancellationRating
7.4
10,234 reviews
Search United Airlines flights
American AirlinesPriceFrom $189Free CancellationRating
7.0
12,085 reviews
Search American Airlines flights
SouthwestPriceFrom $206Free CancellationRating
8.0
4,199 reviews
Search Southwest 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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