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

As of September 2025, 222 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 50% of daily flights taking off at noon.

How long does it take to fly to Chicago?

Average flight duration from Kentucky to Chicago depends on which airport you fly into and out of. Flying from Louisville to Chicago O'Hare Intl Airport is 1h 31m on average, while flying from Lexington to Chicago O'Hare Intl Airport is 1h 36m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

As of September 2025, there are 1,558 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

What airlines fly to Chicago?

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

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

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

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

Prices for flights from Kentucky to Chicago are refreshed on a daily basis.

How many operators does momondo search for flights from Kentucky to Chicago?

As of September 2025, there are 7 operators available to choose from for flights from Kentucky to Chicago.

How old do you have to be to fly from Kentucky to Chicago?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Chicago.

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

The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$49 Cheap Flights from Kentucky to Chicago in 2025/26

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Find the cheapest flights from Kentucky to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:51 am - 10:42 amBNA-ORD

1h 51mnonstop

4:01 pm - 5:41 pmORD-BNA

1h 40mnonstop

$75Multiple Airlines

Find Deal

Mon, Nov 10 - Thu, Nov 13

6:46 pm - 8:31 pmBNA-ORD

1h 45mnonstop

6:20 am - 7:56 amORD-BNA

1h 36mnonstop

$77Multiple Airlines

Find Deal

Fri, Nov 14 - Mon, Nov 17

2:59 pm - 4:56 pmBNA-ORD

1h 57mnonstop

12:43 pm - 2:26 pmORD-BNA

1h 43mnonstop

$78Frontier

Find Deal

Fri, Oct 3 - Mon, Oct 6

3:11 pm - 5:16 pmBNA-ORD

2h 05mnonstop

7:25 pm - 9:09 pmORD-BNA

1h 44mnonstop

$79Frontier

Find Deal

Mon, Oct 6 - Mon, Oct 13

6:46 pm - 8:31 pmBNA-ORD

1h 45mnonstop

4:01 pm - 5:41 pmORD-BNA

1h 40mnonstop

$96Spirit Airlines

Find Deal

Thu, Nov 20 - Mon, Nov 24

5:05 am - 9:33 pmBNA-ORD

16h 28m1 stop

1:26 pm - 3:10 pmORD-BNA

1h 44mnonstop

$114Spirit Airlines

Find Deal

Fri, Oct 17 - Sun, Oct 19

12:43 pm - 1:21 pmSDF-ORD

1h 38mnonstop

8:25 pm - 10:55 pmORD-SDF

1h 30mnonstop

$137American Airlines

Find Deal

Tue, Nov 11 - Tue, Nov 11

8:15 pm - 8:30 pmSDF-MDW

1h 15mnonstop

8:35 pm - 10:45 pmMDW-SDF

1h 10mnonstop

$137Southwest

Find Deal

Mon, Oct 20 - Tue, Oct 21

9:45 pm - 11:15 pmBNA-MDW

1h 30mnonstop

6:45 pm - 8:10 pmMDW-BNA

1h 25mnonstop

$137Southwest

Find Deal

Mon, Oct 20 - Mon, Oct 27

6:45 am - 7:18 amSDF-ORD

1h 33mnonstop

11:21 am - 1:47 pmORD-SDF

1h 26mnonstop

$154American Airlines

Find Deal

Wed, Oct 15 - Sat, Oct 18

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

Frontier

Oct 3

BNA2:59 pmNashville Intl

1h 57m

ORD4:56 pmChicago O'Hare Intl

Oct 6

ORD12:43 pmChicago O'Hare Intl

1h 43m

BNA2:26 pmNashville Intl

$78

Find similar

Frontier

Oct 6

BNA3:11 pmNashville Intl

2h 05m

ORD5:16 pmChicago O'Hare Intl

Oct 13

ORD7:25 pmChicago O'Hare Intl

1h 44m

BNA9:09 pmNashville Intl

$79

Find similar

Frontier

Oct 3

BNA2:59 pmNashville Intl

1h 57m

ORD4:56 pmChicago O'Hare Intl

Oct 5

ORD12:43 pmChicago O'Hare Intl

1h 43m

BNA2:26 pmNashville Intl

$80

Find similar

Spirit Airlines flights from Kentucky to Chicago

Our best Spirit Airlines deals on Kentucky to Chicago flight tickets

Spirit Airlines

Nov 20

BNA6:46 pmNashville Intl

1h 45m

ORD8:31 pmChicago O'Hare Intl

Nov 24

ORD4:01 pmChicago O'Hare Intl

1h 40m

BNA5:41 pmNashville Intl

$96

Find similar

Spirit Airlines

Oct 17

BNA5:05 amNashville Intl

16h 28m

1 stop

ORD9:33 pmChicago O'Hare Intl

Oct 19

ORD1:26 pmChicago O'Hare Intl

1h 44m

BNA3:10 pmNashville Intl

$114

Find similar

Spirit Airlines

Oct 5

BNA9:02 pmNashville Intl

1h 47m

ORD10:49 pmChicago O'Hare Intl

Oct 10

ORD4:44 pmChicago O'Hare Intl

1h 40m

BNA6:24 pmNashville Intl

$120

Find similar

Fly from

Fly to

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Mon 11/10

8:51 am-10:42 am

Nonstop1h 51m

Chicago O'Hare Intl

Thu 11/13

4:01 pm-5:41 pm

Nonstop1h 40m

$75

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 11/14

6:46 pm-8:31 pm

Nonstop1h 45m

Chicago O'Hare Intl

Mon 11/17

6:20 am-7:56 am

Nonstop1h 36m

$77

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 10/3

2:59 pm-4:56 pm

Nonstop1h 57m

Chicago O'Hare Intl

Mon 10/6

12:43 pm-2:26 pm

Nonstop1h 43m

$78

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Mon 10/6

3:11 pm-5:16 pm

Nonstop2h 05m

Chicago O'Hare Intl

Mon 10/13

7:25 pm-9:09 pm

Nonstop1h 44m

$79

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 11/20

6:46 pm-8:31 pm

Nonstop1h 45m

Chicago O'Hare Intl

Mon 11/24

4:01 pm-5:41 pm

Nonstop1h 40m

$96

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 10/17

5:05 am-9:33 pm

1 stop16h 28m

Chicago O'Hare Intl

Sun 10/19

1:26 pm-3:10 pm

Nonstop1h 44m

$114

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 11/11

12:43 pm-1:21 pm

Nonstop1h 38m

Chicago O'Hare Intl

Tue 11/11

8:25 pm-10:55 pm

Nonstop1h 30m

$137

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Mon 10/20

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Tue 10/21

8:35 pm-10:45 pm

Nonstop1h 10m

$137

NashvilleChicago

BNA - MDW

BNAMDW

Nashville Intl

Mon 10/20

9:45 pm-11:15 pm

Nonstop1h 30m

Chicago Midway

Mon 10/27

6:45 pm-8:10 pm

Nonstop1h 25m

$137

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 10/15

6:45 am-7:18 am

Nonstop1h 33m

Chicago O'Hare Intl

Sat 10/18

11:21 am-1:47 pm

Nonstop1h 26m

$154

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How to get the cheapest flight ticket from Kentucky to Chicago

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 Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $196. If you’re not able to fly to Chicago in November, then April is your next best option. Flight prices from Kentucky to Chicago during April average around $207.

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

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $495. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Kentucky to Chicago for around $721.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Kentucky to Chicago during this time can be as low as $528. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $850.

What is the cheapest Kentucky to Chicago flight route?

Fly from Owensboro Daviess County to Chicago O'Hare Intl for the best Kentucky - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $288 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Kentucky for as low as $196 on momondo.

What cabin class options are available on Kentucky to Chicago flights?

There are 4 cabin classes available to choose from on Kentucky to Chicago 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 Kentucky to Chicago flights?

You could potentially save up to 1% on your flight if you consider stops on a Kentucky to Chicago flight.

Cheap Kentucky to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kentucky to Chicago

Best Price Found	$95
Fastest flight time	1h 05m
Direct flights	Every day
Airports in Chicago	1 airport

The best one-way flight to Chicago from Kentucky in the past 72 hours is $95. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $144.

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

Direct flights go from Kentucky to Chicago every day.

There is 1 airport near Chicago: Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Kentucky to Chicago?
Prices for flights from Kentucky to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Kentucky to Chicago?
As of September 2025, there are 7 operators available to choose from for flights from Kentucky to Chicago.
How old do you have to be to fly from Kentucky to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Kentucky to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Kentucky to Chicago is Embraer 175 (Enhanced Winglets) (18.24% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (15.41%), Embraer 175 (12.66%), and Embraer 170 (8.82%).

Best airlines flying from Kentucky to Chicago

Compare and see reviews for airlines that fly from Kentucky to Chicago with momondo

Airline	Rating	Free Cancellation	Price
American Airlines	PriceFrom $97	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights
Contour	PriceFrom $113	Free Cancellation	Rating 7.2 36 reviews	Search Contour flights
United Airlines	PriceFrom $114	Free Cancellation	Rating 7.4 8,922 reviews	Search United Airlines flights

Merrillville

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Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Kentucky to Chicago. momondo saves you time and could save you money on your trip.

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

momondo does allow users to show only those flights to Chicago from Kentucky which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kentucky.

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

If you are not ready to book a flight from Kentucky to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

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Cheap flights from Kentucky to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kentucky to Chicago departing on 10/6. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Kentucky to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

Spirit Airlines flights from Kentucky to Chicago

Our best Spirit Airlines deals on Kentucky to Chicago flight tickets

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Kentucky to Chicago

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 Chicago?

The month of November is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $196. If you’re not able to fly to Chicago in November, then April is your next best option. Flight prices from Kentucky to Chicago during April average around $207.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Kentucky to Chicago during this time can be as low as $528. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $850.

What is the cheapest Kentucky to Chicago flight route?

Fly from Owensboro Daviess County to Chicago O'Hare Intl for the best Kentucky - Chicago flight prices

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

What cabin class options are available on Kentucky to Chicago flights?

There are 4 cabin classes available to choose from on Kentucky to Chicago 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 Kentucky to Chicago flights?

You could potentially save up to 1% on your flight if you consider stops on a Kentucky to Chicago flight.

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

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

What airlines fly to Chicago?

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

As of September 2025, 222 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 50% of daily flights taking off at noon.

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

As of September 2025, there are 1,558 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Mon, with 16% of flights taking off on this day.

How long does it take to fly to Chicago?

Cheap Kentucky to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kentucky to Chicago

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

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

How many operators does momondo search for flights from Kentucky to Chicago?

How old do you have to be to fly from Kentucky to Chicago?

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

What is the most popular plane model from Kentucky to Chicago?

Best airlines flying from Kentucky to Chicago

Compare and see reviews for airlines that fly from Kentucky to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago 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 the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago