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

As of May 2026, 231 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 11:00AM, with 53% of daily flights taking off at noon.

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

As of May 2026, there are 1,620 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Fri, with 16% of flights taking off on this day.

What airlines fly to Chicago?

American Airlines, United Airlines and Contour 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 42% 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?

Frontier, Southwest, and American Airlines 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 Paducah to Chicago O'Hare Intl Airport is 1h 28m on average, while flying from Louisville to Chicago O'Hare Intl Airport is 1h 36m 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 May 2026, 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.

$59 Cheap Flights from Kentucky to Chicago in 2026

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Find the cheapest flights from Kentucky to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:24 pm - 10:11 pm

CVG

MDW

10h 47m

1 stop

6:00 am - 1:55 pm

MDW

CVG

30h 55m

2 stops

$196Multiple Airlines

Tue, Jun 9 - Tue, Jun 16

4:00 pm - 8:31 pm

CVG

ORD

5h 31m

1 stop

8:52 am - 1:35 pm

ORD

CVG

3h 43m

1 stop

$197Delta

Tue, Jun 9 - Tue, Jun 16

12:54 pm - 7:53 am

CVG

ORD

19h 59m

1 stop

1:50 pm - 11:48 am

ORD

CVG

20h 58m

1 stop

$200Frontier

Mon, Jul 6 - Thu, Jul 9

12:27 pm - 7:53 pm

CVG

ORD

8h 26m

1 stop

8:05 am - 11:13 am

ORD

CVG

26h 08m

2 stops

$201Frontier

Tue, Aug 11 - Sat, Aug 15

8:20 pm - 8:30 pm

CVG

MDW

1h 10mnonstop

5:20 pm - 12:20 am

MDW

CVG

6h 00m

1 stop

$201Southwest

Mon, Jun 1 - Thu, Jun 4

1:40 pm - 7:15 pm

CVG

MDW

6h 35m

2 stops

7:05 pm - 9:15 pm

MDW

CVG

1h 10mnonstop

$206Southwest

Sat, Jun 6 - Mon, Jun 8

7:54 am - 9:05 am

TRI

ORD

2h 11mnonstop

9:07 pm - 11:57 pm

ORD

TRI

1h 50mnonstop

$229American Airlines

Thu, Jul 2 - Sat, Jul 11

2:57 pm - 7:45 am

BNA

RFD

16h 48m

1 stop

9:21 am - 10:49 am

RFD

BNA

1h 28mnonstop

$240Allegiant Air

Thu, May 28 - Sun, May 31

7:54 am - 9:05 am

TRI

ORD

2h 11mnonstop

9:25 pm - 12:15 am

ORD

TRI

1h 50mnonstop

$244American Airlines

Thu, Jul 2 - Sun, Jul 5

7:00 am - 8:29 am

BNA

RFD

1h 29mnonstop

11:27 am - 10:37 pm

RFD

BNA

35h 10m

2 stops

$245Allegiant Air

Thu, Jun 11 - Sun, Jun 14

American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

American Airlines

Jun 29

CVG2:05 pmCincinnati Cinci./N. Kentucky

1h 39m

ORD2:44 pmChicago O'Hare Intl

Jun 30

ORD5:30 pmChicago O'Hare Intl

1h 30m

CVG8:00 pmCincinnati Cinci./N. Kentucky

$215

American Airlines

Jun 2

CVG7:00 amCincinnati Cinci./N. Kentucky

6h 18m

1 stop

ORD12:18 pmChicago O'Hare Intl

Jun 3

ORD10:00 pmChicago O'Hare Intl

1h 28m

CVG12:28 amCincinnati Cinci./N. Kentucky

$222

American Airlines

Jun 29

CVG1:30 pmCincinnati Cinci./N. Kentucky

1h 37m

ORD2:07 pmChicago O'Hare Intl

Jun 30

ORD3:29 pmChicago O'Hare Intl

1h 26m

CVG5:55 pmCincinnati Cinci./N. Kentucky

$225

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

Frontier

Jul 6

CVG12:54 pmCincinnati Cinci./N. Kentucky

19h 59m

1 stop

ORD7:53 amChicago O'Hare Intl

Jul 9

ORD1:50 pmChicago O'Hare Intl

20h 58m

1 stop

CVG11:48 amCincinnati Cinci./N. Kentucky

$200

Frontier

Aug 11

CVG12:27 pmCincinnati Cinci./N. Kentucky

8h 26m

1 stop

ORD7:53 pmChicago O'Hare Intl

Aug 15

ORD8:05 amChicago O'Hare Intl

26h 08m

2 stops

CVG11:13 amCincinnati Cinci./N. Kentucky

$201

Frontier

Jun 10

CVG12:54 pmCincinnati Cinci./N. Kentucky

10h 17m

1 stop

MDW10:11 pmChicago Midway

Jun 18

MDW12:27 pmChicago Midway

22h 22m

1 stop

CVG11:49 amCincinnati Cinci./N. Kentucky

$203

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 6/9

12:24 pm-10:11 pm

1 stop10h 47m

Chicago Midway

Tue 6/16

6:00 am-1:55 pm

2 stops30h 55m

$196

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Tue 6/9

4:00 pm-8:31 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 6/16

8:52 am-1:35 pm

1 stop3h 43m

$197

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 7/6

12:54 pm-7:53 am

1 stop19h 59m

Chicago O'Hare Intl

Thu 7/9

1:50 pm-11:48 am

1 stop20h 58m

$200

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Tue 8/11

12:27 pm-7:53 pm

1 stop8h 26m

Chicago O'Hare Intl

Sat 8/15

8:05 am-11:13 am

2 stops26h 08m

$201

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 6/1

8:20 pm-8:30 pm

Nonstop1h 10m

Chicago Midway

Thu 6/4

5:20 pm-12:20 am

1 stop6h 00m

$201

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 6/6

1:40 pm-7:15 pm

2 stops6h 35m

Chicago Midway

Mon 6/8

7:05 pm-9:15 pm

Nonstop1h 10m

$206

Quickest round-trip

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 7/2

7:54 am-9:05 am

Nonstop2h 11m

Chicago O'Hare Intl

Sat 7/11

9:07 pm-11:57 pm

Nonstop1h 50m

$229

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Thu 5/28

2:57 pm-7:45 am

1 stop16h 48m

Chicago Greater Rockford

Sun 5/31

9:21 am-10:49 am

Nonstop1h 28m

$240

BlountvilleChicago

TRI - ORD

TRIORD

Blountville Tri Cities TN/VA

Thu 7/2

7:54 am-9:05 am

Nonstop2h 11m

Chicago O'Hare Intl

Sun 7/5

9:25 pm-12:15 am

Nonstop1h 50m

$244

NashvilleChicago

BNA - RFD

BNARFD

Nashville Intl

Thu 6/11

7:00 am-8:29 am

Nonstop1h 29m

Chicago Greater Rockford

Sun 6/14

11:27 am-10:37 pm

2 stops35h 10m

$245

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 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 $58. If you’re not able to fly to Chicago in April, then January is your next best option. Flight prices from Kentucky to Chicago during January average around $67.

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 Friday when prices can be found for as low as $489. 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 $630.

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 $486. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $874.

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 from Kentucky 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 $295 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 $95 on momondo.

Can stopping save me money on Kentucky to Chicago flights?

You could potentially save up to 17% 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	$58
Fastest flight time	1h 05m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Kentucky in the past 72 hours is $58. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $126.

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

Direct flights go from Kentucky to Chicago every day.

There are 3 airports in Chicago. From Kentucky there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).

Search flight deals

Frequently asked questions about flying 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 May 2026, 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 Canadair (Bombardier) Regional Jet CRJ-550 (16.88% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (16.65%), Embraer 175 (13.08%), and Boeing 737 MAX 8 (9.58%).

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 7.1 11,669 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,305 reviews	Search Southwest flights
Contour	PriceFrom $108	Free Cancellation	Rating 7.7 41 reviews	Search Contour flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 9,696 reviews	Search United Airlines flights

Merrillville

New Buffalo

Hammond

Saint Joseph

Benton Harbor

Portage

Lansing

Valparaiso

Munster

Schererville

Crown Point

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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Fly into one of these airports located in Chicago

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Cheap flights from Kentucky to Chicago from $67

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 6/9. 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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American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

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How to get the cheapest flight ticket from Kentucky to Chicago

What is the cheapest month to fly to Chicago?

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?

What is the cheapest Kentucky to Chicago flight route?

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

Can stopping save me money on Kentucky to Chicago flights?

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

What airlines fly to Chicago?

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

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

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

Frequently asked questions about flying 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?

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

Fly your favorite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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

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