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

As of July 2025, there are 1,409 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.

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

As of July 2025, 201 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 43% of daily flights taking off at noon.

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 47% 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

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 30m on average, while flying from Lexington to Chicago O'Hare Intl Airport is 1h 33m on average. Chicago O'Hare Intl Airport is the most popular airport in 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 July 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.

$28 Cheap Flights from Kentucky to Chicago in 2025

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Find the cheapest flights from Kentucky to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:23 pm - 1:56 pmTYS-MDW

1h 33mnonstop

2:46 pm - 5:12 pmMDW-TYS

1h 26mnonstop

$48Allegiant Air

Find Deal

Mon, Aug 4 - Fri, Aug 8

2:29 pm - 3:02 pmTYS-MDW

1h 33mnonstop

3:52 pm - 6:20 pmMDW-TYS

1h 28mnonstop

$50Allegiant Air

Find Deal

Fri, Aug 22 - Mon, Aug 25

7:27 pm - 9:30 pmBNA-ORD

2h 03mnonstop

4:37 pm - 6:06 pmORD-BNA

1h 29mnonstop

$58Spirit Airlines

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Fri, Aug 8 - Mon, Aug 11

7:27 pm - 9:30 pmBNA-ORD

2h 03mnonstop

4:37 pm - 6:06 pmORD-BNA

1h 29mnonstop

$60Spirit Airlines

Find Deal

Fri, Aug 8 - Mon, Aug 11

7:27 pm - 9:30 pmBNA-ORD

2h 03mnonstop

12:35 pm - 2:14 pmORD-BNA

1h 39mnonstop

$80

Find Deal

Mon, Aug 11 - Mon, Aug 18

3:11 pm - 5:16 pmBNA-ORD

2h 05mnonstop

12:48 pm - 2:26 pmORD-BNA

1h 38mnonstop

$90Frontier

Find Deal

Fri, Sep 19 - Mon, Sep 22

3:11 pm - 5:16 pmBNA-ORD

2h 05mnonstop

12:48 pm - 2:26 pmORD-BNA

1h 38mnonstop

$91Frontier

Find Deal

Fri, Sep 19 - Sun, Sep 21

8:40 am - 9:17 amSDF-ORD

1h 37mnonstop

2:20 pm - 4:51 pmORD-SDF

1h 31mnonstop

$97United Airlines

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Thu, Aug 7 - Thu, Aug 14

4:57 pm - 6:50 pmBNA-ORD

1h 53mnonstop

7:17 am - 8:57 amORD-BNA

1h 40mnonstop

$97United Airlines

Find Deal

Sat, Sep 6 - Mon, Sep 8

5:05 am - 4:12 pmBNA-ORD

11h 07m1 stop

12:48 pm - 2:26 pmORD-BNA

1h 38mnonstop

$100

Find Deal

Sat, Sep 6 - Mon, Sep 8

United Airlines flights from Kentucky to Chicago

Our best United Airlines deals on Kentucky to Chicago flight tickets

United Airlines

Aug 7

SDF8:40 amLouisville Intl

1h 37m

ORD9:17 amChicago O'Hare Intl

Aug 14

ORD2:20 pmChicago O'Hare Intl

1h 31m

SDF4:51 pmLouisville Intl

$97

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United Airlines

Sep 4

SDF7:00 amLouisville Intl

1h 38m

ORD7:38 amChicago O'Hare Intl

Sep 7

ORD7:26 amChicago O'Hare Intl

1h 36m

SDF10:02 amLouisville Intl

$124

Find similar

United Airlines

Jul 29

TYS7:00 amKnoxville McGhee Tyson

1h 57m

ORD7:57 amChicago O'Hare Intl

Aug 2

ORD7:50 pmChicago O'Hare Intl

1h 45m

TYS10:35 pmKnoxville McGhee Tyson

$199

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American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

American Airlines

Aug 7

SDF6:44 amLouisville Intl

1h 46m

ORD7:30 amChicago O'Hare Intl

Aug 11

ORD8:32 pmChicago O'Hare Intl

1h 41m

SDF11:13 pmLouisville Intl

$98

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American Airlines

Sep 10

BNA7:20 amNashville Intl

2h 00m

ORD9:20 amChicago O'Hare Intl

Sep 14

ORD6:54 amChicago O'Hare Intl

1h 34m

BNA8:28 amNashville Intl

$127

Find similar

American Airlines

Aug 30

CVG9:45 amCincinnati Cinci./N. Kentucky

1h 30m

ORD10:15 amChicago O'Hare Intl

Aug 30

ORD3:04 pmChicago O'Hare Intl

1h 19m

CVG5:23 pmCincinnati Cinci./N. Kentucky

$161

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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 April is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $207. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Kentucky to Chicago during August average around $243.

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 $483. 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 $706.

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 $517. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $867.

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 $280 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 $166 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?

No. A direct flight is the cheapest option for a flight between Kentucky 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	$28
Fastest flight time	1h 05m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Kentucky in the past 72 hours is $28. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $48.

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

Direct flights go from Kentucky to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), 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 July 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) (18.55% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (14.18%), Embraer 170 (12.22%), and Embraer 175 (10.97%).

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
United Airlines	PriceFrom $99	Free Cancellation	Rating 7.4 8,863 reviews	Search United Airlines flights
American Airlines	PriceFrom $101	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
Contour	PriceFrom $116	Free Cancellation	Rating 7.1 32 reviews	Search Contour flights
Southwest	PriceFrom $156	Free Cancellation	Rating 8.0 4,239 reviews	Search Southwest flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Monticello

Chesterton

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 $28

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 11/7. 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

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

United Airlines flights from Kentucky to Chicago

Our best United Airlines deals on Kentucky to Chicago flight tickets

American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

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 April is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $207. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Kentucky to Chicago during August average around $243.

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 $517. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $867.

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?

No. A direct flight is the cheapest option for a flight between Kentucky to Chicago.

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 July 2025, 201 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 2:00PM, with 43% of daily flights taking off at noon.

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

As of July 2025, there are 1,409 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Mon, with 18% 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