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

1,130 flights are operational weekly from Chicago to Kentucky as of July 2025. The most popular departure day for this route is Thu, with 20% of flights per week taking off on this day.

What airlines fly to Kentucky?

American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Kentucky from Chicago according to our data. American Airlines is the first choice among our users, with 42% 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 July 2025, there are 161 flights per day flying from Chicago to Kentucky. The most common time of day flights depart is 8:00PM, with 40% of flights taking off in the afternoon.

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

Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating 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 July 2025.

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.

$30 Cheap Flights from Chicago to Kentucky in 2025

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Find the cheapest flights from Chicago to Kentucky

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

4:01 pm - 5:41 pmORD-BNA

1h 40mnonstop

6:46 pm - 8:31 pmBNA-ORD

1h 45mnonstop

$64Spirit Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

12:05 pm - 1:35 pmORD-BNA

1h 30mnonstop

7:25 pm - 9:19 pmBNA-ORD

1h 54mnonstop

$66Spirit Airlines

Find Deal

Sun, Oct 19 - Thu, Oct 23

1:52 pm - 3:35 pmORD-BNA

1h 43mnonstop

4:20 pm - 6:15 pmBNA-ORD

1h 55mnonstop

$74Frontier

Find Deal

Thu, Oct 23 - Fri, Oct 24

1:52 pm - 3:35 pmORD-BNA

1h 43mnonstop

4:20 pm - 6:15 pmBNA-ORD

1h 55mnonstop

$75Frontier

Find Deal

Thu, Oct 30 - Mon, Nov 3

7:26 am - 10:00 amORD-SDF

1h 34mnonstop

7:36 pm - 8:25 pmSDF-ORD

1h 49mnonstop

$97United Airlines

Find Deal

Sat, Aug 23 - Sat, Aug 23

2:55 pm - 4:30 pmORD-BNA

1h 35mnonstop

10:50 am - 12:45 pmBNA-ORD

1h 55mnonstop

$97Southwest

Find Deal

Sat, Sep 13 - Tue, Sep 16

7:25 am - 8:50 amMDW-BNA

1h 25mnonstop

8:50 pm - 10:25 pmBNA-MDW

1h 35mnonstop

$97Southwest

Find Deal

Wed, Sep 17 - Wed, Sep 17

7:26 am - 10:02 amORD-SDF

1h 36mnonstop

10:55 am - 11:33 amSDF-ORD

1h 38mnonstop

$113United Airlines

Find Deal

Wed, Sep 10 - Wed, Sep 17

11:52 am - 2:19 pmORD-SDF

1h 27mnonstop

2:42 pm - 3:24 pmSDF-ORD

1h 42mnonstop

$124American Airlines

Find Deal

Sat, Aug 23 - Mon, Aug 25

3:17 pm - 5:43 pmORD-SDF

1h 26mnonstop

2:42 pm - 3:24 pmSDF-ORD

1h 42mnonstop

$138American Airlines

Find Deal

Sat, Aug 30 - Sun, Aug 31

Frontier flights from Chicago to Kentucky

Our best Frontier deals on Chicago to Kentucky flight tickets

Frontier

Oct 23

ORD1:52 pmChicago O'Hare Intl

1h 43m

BNA3:35 pmNashville Intl

Oct 24

BNA4:20 pmNashville Intl

1h 55m

ORD6:15 pmChicago O'Hare Intl

$74

Find similar

Frontier

Oct 30

ORD1:52 pmChicago O'Hare Intl

1h 43m

BNA3:35 pmNashville Intl

Nov 3

BNA4:20 pmNashville Intl

1h 55m

ORD6:15 pmChicago O'Hare Intl

$75

Find similar

Frontier

Sep 4

ORD12:53 pmChicago O'Hare Intl

1h 43m

BNA2:36 pmNashville Intl

Sep 8

BNA3:21 pmNashville Intl

2h 05m

ORD5:26 pmChicago O'Hare Intl

$77

Find similar

Spirit Airlines flights from Chicago to Kentucky

Our best Spirit Airlines deals on Chicago to Kentucky flight tickets

Spirit Airlines

Nov 10

ORD4:01 pmChicago O'Hare Intl

1h 40m

BNA5:41 pmNashville Intl

Nov 13

BNA6:46 pmNashville Intl

1h 45m

ORD8:31 pmChicago O'Hare Intl

$64

Find similar

Spirit Airlines

Oct 19

ORD12:05 pmChicago O'Hare Intl

1h 30m

BNA1:35 pmNashville Intl

Oct 23

BNA7:25 pmNashville Intl

1h 54m

ORD9:19 pmChicago O'Hare Intl

$66

Find similar

Spirit Airlines

Oct 19

ORD12:05 pmChicago O'Hare Intl

1h 30m

BNA1:35 pmNashville Intl

Oct 23

BNA7:25 pmNashville Intl

1h 54m

ORD9:19 pmChicago O'Hare Intl

$68

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Mon 11/10

4:01 pm-5:41 pm

Nonstop1h 40m

Nashville Intl

Thu 11/13

6:46 pm-8:31 pm

Nonstop1h 45m

$64

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sun 10/19

12:05 pm-1:35 pm

Nonstop1h 30m

Nashville Intl

Thu 10/23

7:25 pm-9:19 pm

Nonstop1h 54m

$66

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/23

1:52 pm-3:35 pm

Nonstop1h 43m

Nashville Intl

Fri 10/24

4:20 pm-6:15 pm

Nonstop1h 55m

$74

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Thu 10/30

1:52 pm-3:35 pm

Nonstop1h 43m

Nashville Intl

Mon 11/3

4:20 pm-6:15 pm

Nonstop1h 55m

$75

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 8/23

7:26 am-10:00 am

Nonstop1h 34m

Louisville Intl

Sat 8/23

7:36 pm-8:25 pm

Nonstop1h 49m

$97

ChicagoNashville

ORD - BNA

ORDBNA

Chicago O'Hare Intl

Sat 9/13

2:55 pm-4:30 pm

Nonstop1h 35m

Nashville Intl

Tue 9/16

10:50 am-12:45 pm

Nonstop1h 55m

$97

ChicagoNashville

MDW - BNA

MDWBNA

Chicago Midway

Wed 9/17

7:25 am-8:50 am

Nonstop1h 25m

Nashville Intl

Wed 9/17

8:50 pm-10:25 pm

Nonstop1h 35m

$97

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Wed 9/10

7:26 am-10:02 am

Nonstop1h 36m

Louisville Intl

Wed 9/17

10:55 am-11:33 am

Nonstop1h 38m

$113

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 8/23

11:52 am-2:19 pm

Nonstop1h 27m

Louisville Intl

Mon 8/25

2:42 pm-3:24 pm

Nonstop1h 42m

$124

ChicagoLouisville

ORD - SDF

ORDSDF

Chicago O'Hare Intl

Sat 8/30

3:17 pm-5:43 pm

Nonstop1h 26m

Louisville Intl

Sun 8/31

2:42 pm-3:24 pm

Nonstop1h 42m

$138

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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 August, then May is your next best option. Flight prices from Chicago to Kentucky during May average around $227.

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 $267. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $575. 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 $291. 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 morning when prices are around $321.

What is the cheapest Chicago to Kentucky flight route?

Fly from Chicago Midway to Louisville Intl 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 $340 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	$30
Fastest flight time	1h 05m
Direct flights	Every day
Airports in Kentucky	4 airports

The best one-way flight to Kentucky from Chicago in the past 72 hours is $30. The best round-trip flight deal from Chicago to Kentucky found on momondo in the last 72 hours is $64.

The fastest flight from Chicago to Kentucky takes 1h 05m

Direct flights go from Chicago to Kentucky every day.

There are 4 airports near Kentucky: Nashville Intl (BNA), Louisville Intl (SDF), Cincinnati Cinci./N. Kentucky (CVG), Knoxville McGhee Tyson (TYS)

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?
The number of operators available for flights from Chicago to Kentucky is 7 as of July 2025.
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 Embraer 175 (Enhanced Winglets), making up 19.22% of the total bookings. Other popular models include Canadair (Bombardier) Regional Jet CRJ-550 with 18.66%, Embraer 170 with 13.33%, and Embraer 175 with 9.77%.

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 $102	Free Cancellation	Rating 7.1 32 reviews	Search Contour flights
Southwest	PriceFrom $124	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
American Airlines	PriceFrom $132	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $137	Free Cancellation	Rating 7.4 8,900 reviews	Search United 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

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.

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Find better results for your trip to Kentucky

Popular cities in Kentucky

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Cheap flights from Chicago to Kentucky from $30

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 10/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

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Price Alerts

Find the cheapest flights from Chicago to Kentucky

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Chicago to Kentucky

Our best Frontier deals on Chicago to Kentucky flight tickets

Spirit Airlines flights from Chicago to Kentucky

Our best Spirit Airlines deals on Chicago to Kentucky flight tickets

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Use the filters below to find and compare flights from Chicago to Kentucky that are best for you.

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 May is your next best option. Flight prices from Chicago to Kentucky during May average around $227.

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?

Fly from Chicago Midway to Louisville Intl for the best Chicago - Kentucky flight prices

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

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.

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

Spirit Airlines, Frontier, and United Airlines are the most popular carriers operating from Chicago to Kentucky

What airlines fly to Kentucky?

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

As of July 2025, there are 161 flights per day flying from Chicago to Kentucky. The most common time of day flights depart is 8:00PM, with 40% of flights taking off in the afternoon.

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

1,130 flights are operational weekly from Chicago to Kentucky as of July 2025. The most popular departure day for this route is Thu, with 20% of flights per week taking off on this day.

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

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

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?

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

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

Why use momondo?

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

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

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

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

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