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

Southwest, United Airlines, and American Airlines are the most popular carriers operating from Kentucky to Chicago

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

As of February 2026, 67 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 8:00AM, with 45% of daily flights taking off in the afternoon.

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

As of February 2026, there are 471 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Wed, with 39% 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 43% 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.

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 February 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.

$56 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.

5:35 am - 6:19 am

SDF

ORD

1h 44mnonstop

5:50 pm - 8:14 pm

ORD

SDF

1h 24mnonstop

$137United Airlines

Sat, Mar 7 - Sat, Mar 14

1:22 pm - 1:57 pm

TYS

MDW

1h 35mnonstop

2:47 pm - 5:13 pm

MDW

TYS

1h 26mnonstop

$144Allegiant Air

Thu, May 21 - Sun, May 24

6:00 am - 6:40 am

SDF

ORD

1h 40mnonstop

6:57 pm - 9:30 pm

ORD

SDF

1h 33mnonstop

$147American Airlines

Sat, May 16 - Sat, May 16

8:55 am - 9:15 am

SDF

MDW

1h 20mnonstop

6:15 pm - 8:30 pm

MDW

SDF

1h 15mnonstop

$177Southwest

Tue, Mar 10 - Wed, Mar 11

6:00 am - 6:40 am

SDF

ORD

1h 40mnonstop

8:02 am - 10:43 am

ORD

SDF

1h 41mnonstop

$181American Airlines

Thu, Apr 30 - Sat, May 2

7:05 pm - 7:25 pm

SDF

MDW

1h 20mnonstop

3:35 pm - 11:30 pm

MDW

SDF

6h 55m

1 stop

$187Southwest

Tue, Mar 10 - Wed, Mar 11

1:07 pm - 10:39 pm

CVG

ORD

10h 32m

1 stop

5:01 am - 6:45 pm

ORD

CVG

12h 44m

1 stop

$187Frontier

Thu, Mar 5 - Sun, Mar 8

7:59 pm - 5:41 pm

CVG

ORD

22h 42m

2 stops

4:21 pm - 7:23 pm

ORD

CVG

26h 02m

1 stop

$188Frontier

Fri, Apr 17 - Wed, Apr 29

8:05 am - 6:40 pm

CVG

MDW

11h 35m

2 stops

9:35 am - 1:31 pm

MDW

CVG

2h 56m

1 stop

$189Delta

Wed, Mar 4 - Mon, Mar 9

6:00 am - 10:14 am

CVG

ORD

5h 14m

1 stop

7:10 am - 1:31 pm

ORD

CVG

5h 21m

1 stop

$191Delta

Thu, Mar 5 - Mon, Mar 9

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

Frontier

Mar 5

CVG1:07 pmCincinnati Cinci./N. Kentucky

10h 32m

1 stop

ORD10:39 pmChicago O'Hare Intl

Mar 8

ORD5:01 amChicago O'Hare Intl

12h 44m

1 stop

CVG6:45 pmCincinnati Cinci./N. Kentucky

$187

Frontier

Apr 17

CVG7:59 pmCincinnati Cinci./N. Kentucky

22h 42m

2 stops

ORD5:41 pmChicago O'Hare Intl

Apr 29

ORD4:21 pmChicago O'Hare Intl

26h 02m

1 stop

CVG7:23 pmCincinnati Cinci./N. Kentucky

$188

Frontier

Apr 22

CVG5:20 pmCincinnati Cinci./N. Kentucky

16h 55m

1 stop

ORD9:15 amChicago O'Hare Intl

Apr 24

ORD6:57 amChicago O'Hare Intl

7h 55m

1 stop

CVG3:52 pmCincinnati Cinci./N. Kentucky

$192

Delta flights from Kentucky to Chicago

Our best Delta deals on Kentucky to Chicago flight tickets

Delta

Mar 4

CVG8:05 amCincinnati Cinci./N. Kentucky

11h 35m

2 stops

MDW6:40 pmChicago Midway

Mar 9

MDW9:35 amChicago Midway

2h 56m

1 stop

CVG1:31 pmCincinnati Cinci./N. Kentucky

$189

Delta

Mar 5

CVG6:00 amCincinnati Cinci./N. Kentucky

5h 14m

1 stop

ORD10:14 amChicago O'Hare Intl

Mar 9

ORD7:10 amChicago O'Hare Intl

5h 21m

1 stop

CVG1:31 pmCincinnati Cinci./N. Kentucky

$191

Delta

Mar 7

CVG6:00 amCincinnati Cinci./N. Kentucky

4h 41m

1 stop

ORD9:41 amChicago O'Hare Intl

Mar 10

ORD7:10 amChicago O'Hare Intl

5h 21m

1 stop

CVG1:31 pmCincinnati Cinci./N. Kentucky

$194

Fly from

Fly to

Route

Depart

Return

Price

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 3/7

5:35 am-6:19 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 3/14

5:50 pm-8:14 pm

Nonstop1h 24m

$137

KnoxvilleChicago

TYS - MDW

TYSMDW

Knoxville McGhee Tyson

Thu 5/21

1:22 pm-1:57 pm

Nonstop1h 35m

Chicago Midway

Sun 5/24

2:47 pm-5:13 pm

Nonstop1h 26m

$144

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 5/16

6:00 am-6:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Sat 5/16

6:57 pm-9:30 pm

Nonstop1h 33m

$147

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/10

8:55 am-9:15 am

Nonstop1h 20m

Chicago Midway

Wed 3/11

6:15 pm-8:30 pm

Nonstop1h 15m

$177

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 4/30

6:00 am-6:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Sat 5/2

8:02 am-10:43 am

Nonstop1h 41m

$181

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 3/10

7:05 pm-7:25 pm

Nonstop1h 20m

Chicago Midway

Wed 3/11

3:35 pm-11:30 pm

1 stop6h 55m

$187

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 3/5

1:07 pm-10:39 pm

1 stop10h 32m

Chicago O'Hare Intl

Sun 3/8

5:01 am-6:45 pm

1 stop12h 44m

$187

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Fri 4/17

7:59 pm-5:41 pm

2 stops22h 42m

Chicago O'Hare Intl

Wed 4/29

4:21 pm-7:23 pm

1 stop26h 02m

$188

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 3/4

8:05 am-6:40 pm

2 stops11h 35m

Chicago Midway

Mon 3/9

9:35 am-1:31 pm

1 stop2h 56m

$189

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 3/5

6:00 am-10:14 am

1 stop5h 14m

Chicago O'Hare Intl

Mon 3/9

7:10 am-1:31 pm

1 stop5h 21m

$191

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 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 $204.

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 $491. 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 $728.

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 $496. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $887.

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 $293 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 $141 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 15% 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	$190
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 $190. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $106.

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 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 February 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 Embraer 175 (Enhanced Winglets) (17.92% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (15.41%), Embraer 175 (11.03%), and Boeing 737 MAX 8 (9.08%).

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 $97	Free Cancellation	Rating 7.4 9,281 reviews	Search United Airlines flights
American Airlines	PriceFrom $97	Free Cancellation	Rating 7.2 11,271 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,280 reviews	Search Southwest flights
Contour	PriceFrom $108	Free Cancellation	Rating 7.6 42 reviews	Search Contour flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

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.

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

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Cheap flights from Kentucky to Chicago from $56

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 4/11. 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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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 to Chicago?

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

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

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

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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