What is the cheapest airline that flies from Chicago to Kentucky?

Allegiant Air, Delta, and Southwest are the most popular carriers operating from Chicago to Kentucky

How many flights depart from Chicago to Kentucky on average per week?

1,406 flights are operational weekly from Chicago to Kentucky as of May 2026. The most popular departure day for this route is Tue, with 18% of flights per week taking off on this day.

What airlines fly to Kentucky?

United Airlines, American Airlines and Contour are the top three most popular airlines that fly to Kentucky from Chicago according to our data. United Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Kentucky. Keep in mind that there are 4 different airlines that fly to Kentucky on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Kentucky on average per day?

As of May 2026, there are 200 flights per day flying from Chicago to Kentucky. The most common time of day flights depart is 9:00PM, with 47% of flights taking off in the evening.

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?

The number of operators available for flights from Chicago to Kentucky is 7 as of May 2026.

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.

$57 Cheap Flights from Chicago to Kentucky in 2026

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Find the cheapest flights from Chicago to Kentucky

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:48 pm - 5:18 pm

MDW

TYS

1h 30mnonstop

1:22 pm - 1:58 pm

TYS

MDW

1h 36mnonstop

$137Allegiant Air

Thu, Jul 16 - Sun, Jul 19

12:27 pm - 11:41 am

MDW

CVG

22h 14m

1 stop

12:24 pm - 10:11 pm

CVG

MDW

10h 47m

1 stop

$139Frontier

Tue, Jun 2 - Tue, Jun 9

1:01 pm - 3:30 pm

ORD

CVG

1h 29mnonstop

6:01 am - 6:30 am

CVG

ORD

1h 29mnonstop

$157American Airlines

Tue, Jun 2 - Tue, Jun 9

6:10 pm - 8:20 pm

MDW

CVG

1h 10mnonstop

7:40 pm - 7:50 pm

CVG

MDW

1h 10mnonstop

$157Southwest

Tue, Jun 2 - Tue, Jun 9

12:50 pm - 3:00 pm

MDW

CVG

1h 10mnonstop

6:35 pm - 9:10 pm

CVG

MDW

3h 35m

1 stop

$167Southwest

Tue, Jun 2 - Tue, Jun 9

12:46 pm - 3:16 pm

ORD

CVG

1h 30mnonstop

9:08 am - 9:45 am

CVG

ORD

1h 37mnonstop

$174United Airlines

Wed, Jun 3 - Sat, Jun 6

10:17 am - 12:51 pm

ORD

CVG

1h 34mnonstop

8:59 pm - 9:41 pm

CVG

ORD

1h 42mnonstop

$191American Airlines

Thu, May 28 - Thu, May 28

12:30 pm - 4:10 pm

ORD

BNA

3h 40m

1 stop

8:00 am - 11:30 am

BNA

ORD

3h 30m

1 stop

$234Contour

Sun, Aug 2 - Wed, Aug 5

12:20 pm - 4:10 pm

ORD

BNA

3h 50m

1 stop

8:00 am - 11:30 am

BNA

ORD

3h 30m

1 stop

$236Contour

Sun, Jul 12 - Wed, Jul 15

8:40 am - 10:34 am

ORD

BNA

1h 54mnonstop

4:58 pm - 6:59 pm

BNA

ORD

2h 01mnonstop

$237United Airlines

Wed, May 27 - Wed, May 27

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Contour flights from Chicago to Kentucky

Our best Contour deals on Chicago to Kentucky flight tickets

Contour

Aug 2

ORD12:30 pmChicago O'Hare Intl

3h 40m

1 stop

BNA4:10 pmNashville Intl

Aug 5

BNA8:00 amNashville Intl

3h 30m

1 stop

ORD11:30 amChicago O'Hare Intl

$234

Contour

Jul 12

ORD12:20 pmChicago O'Hare Intl

3h 50m

1 stop

BNA4:10 pmNashville Intl

Jul 15

BNA8:00 amNashville Intl

3h 30m

1 stop

ORD11:30 amChicago O'Hare Intl

$236

Contour

Jul 23

ORD12:20 pmChicago O'Hare Intl

3h 50m

1 stop

BNA4:10 pmNashville Intl

Jul 26

BNA8:00 amNashville Intl

3h 30m

1 stop

ORD11:30 amChicago O'Hare Intl

$238

Southwest flights from Chicago to Kentucky

Our best Southwest deals on Chicago to Kentucky flight tickets

Southwest

Jun 2

MDW6:10 pmChicago Midway

1h 10m

CVG8:20 pmCincinnati Cinci./N. Kentucky

Jun 9

CVG7:40 pmCincinnati Cinci./N. Kentucky

1h 10m

MDW7:50 pmChicago Midway

$157

Southwest

Jun 2

MDW12:50 pmChicago Midway

1h 10m

CVG3:00 pmCincinnati Cinci./N. Kentucky

Jun 9

CVG6:35 pmCincinnati Cinci./N. Kentucky

3h 35m

1 stop

MDW9:10 pmChicago Midway

$167

Southwest

Jun 3

MDW12:50 pmChicago Midway

1h 10m

CVG3:00 pmCincinnati Cinci./N. Kentucky

Jun 6

CVG7:10 pmCincinnati Cinci./N. Kentucky

1h 10m

MDW7:20 pmChicago Midway

$174

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

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

$137

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 6/2

12:27 pm-11:41 am

1 stop22h 14m

Cincinnati Cinci./N. Kentucky

Tue 6/9

12:24 pm-10:11 pm

1 stop10h 47m

$139

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Tue 6/2

1:01 pm-3:30 pm

Nonstop1h 29m

Cincinnati Cinci./N. Kentucky

Tue 6/9

6:01 am-6:30 am

Nonstop1h 29m

$157

Quickest round-trip

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 6/2

6:10 pm-8:20 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Tue 6/9

7:40 pm-7:50 pm

Nonstop1h 10m

$157

ChicagoCincinnati

MDW - CVG

MDWCVG

Chicago Midway

Tue 6/2

12:50 pm-3:00 pm

Nonstop1h 10m

Cincinnati Cinci./N. Kentucky

Tue 6/9

6:35 pm-9:10 pm

1 stop3h 35m

$167

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Wed 6/3

12:46 pm-3:16 pm

Nonstop1h 30m

Cincinnati Cinci./N. Kentucky

Sat 6/6

9:08 am-9:45 am

Nonstop1h 37m

$174

ChicagoCincinnati

ORD - CVG

ORDCVG

Chicago O'Hare Intl

Thu 5/28

10:17 am-12:51 pm

Nonstop1h 34m

Cincinnati Cinci./N. Kentucky

Thu 5/28

8:59 pm-9:41 pm

Nonstop1h 42m

$191

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 8/2

12:30 pm-4:10 pm

1 stop3h 40m

Nashville Intl

Wed 8/5

8:00 am-11:30 am

1 stop3h 30m

$234

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 7/12

12:20 pm-4:10 pm

1 stop3h 50m

Nashville Intl

Wed 7/15

8:00 am-11:30 am

1 stop3h 30m

$236

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Wed 5/27

8:40 am-10:34 am

Nonstop1h 54m

Nashville Intl

Wed 5/27

4:58 pm-6:59 pm

Nonstop2h 01m

$237

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Kentucky?

If you’re not able to fly to Kentucky in July, then October is your next best option. Flight prices from Chicago to Kentucky during October average around $77.

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 $236. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $471. 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 $308. 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 $383.

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 $339 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 $220 on momondo.

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	$103
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 $103. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $206.

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), 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?
The number of operators available for flights from Chicago to Kentucky is 7 as of May 2026.
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?
Based on momondo bookings for flights between Chicago and Kentucky, the leading plane model is Canadair (Bombardier) Regional Jet CRJ-550, making up 23.22% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 20.21%, Embraer 175 with 18.37%, and Embraer 170 with 11.54%.

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
Contour	PriceFrom $104	Free Cancellation	Rating 7.7 41 reviews	Search Contour flights
Southwest	PriceFrom $124	Free Cancellation	Rating 7.9 4,305 reviews	Search Southwest flights
United Airlines	PriceFrom $133	Free Cancellation	Rating 7.4 9,684 reviews	Search United Airlines flights
American Airlines	PriceFrom $136	Free Cancellation	Rating 7.1 11,667 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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Popular cities in Kentucky

Flights to New Yorkfrom $72

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Flights to Las Vegasfrom $56

Flights to Washington, D.C.from $55

Flights to Bostonfrom $92

Flights to Atlantafrom $55

Flights to Dallasfrom $76

Flights to Fort Lauderdalefrom $56

Cheap flights from Chicago to Kentucky from $52

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 8/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Contour flights from Chicago to Kentucky

Our best Contour deals on Chicago to Kentucky flight tickets

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Our best Southwest deals on Chicago to Kentucky flight tickets

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See travel insights to Kentucky from

How to get the cheapest flight ticket from Chicago to Kentucky

What is the cheapest month to fly to Kentucky?

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

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

What is the cheapest Chicago to Kentucky flight route?

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

Can stopping save me money on Chicago to Kentucky flights?

What is the cheapest airline that flies from Chicago to Kentucky?

What airlines fly to Kentucky?

How many flights depart from Chicago to Kentucky on average per day?

How many flights depart from Chicago to Kentucky on average per week?

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

Fastest flight time

Direct flights

Airports in Kentucky

Frequently asked questions about flying 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

Why use momondo?

An easier way to manage your Kentucky trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Kentucky

Popular cities in Kentucky

Popular flights according to clicks in the last 7 days on momondo

Chicago flight routes

According to popular flight searches on momondo this year

Kentucky flight routes

According to popular flight searches on momondo this year

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