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 Lexington to Chicago O'Hare Intl Airport is 1h 33m 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.

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

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

As of November 2025, 191 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 46% of daily flights taking off at noon.

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

As of November 2025, there are 1,340 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Thu, with 17% of flights taking off on this day.

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 November 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.

$48 Cheap Flights from Kentucky to Chicago in 2025/26

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Cheap round-trip flights

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8:45 am - 10:38 amBNA-ORD

1h 53mnonstop

6:13 am - 7:50 amORD-BNA

1h 37mnonstop

$77Frontier

Find Deal

Fri, Nov 21 - Mon, Nov 24

8:45 am - 10:38 amBNA-ORD

1h 53mnonstop

6:13 am - 7:50 amORD-BNA

1h 37mnonstop

$78Frontier

Find Deal

Mon, Nov 24 - Fri, Nov 28

6:27 am - 7:06 amSDF-ORD

1h 39mnonstop

10:53 am - 1:30 pmORD-SDF

1h 37mnonstop

$97American Airlines

Find Deal

Thu, Dec 25 - Thu, Jan 1

8:29 am - 9:13 amSDF-ORD

1h 44mnonstop

5:50 pm - 8:28 pmORD-SDF

1h 38mnonstop

$99United Airlines

Find Deal

Wed, Jan 14 - Sat, Jan 17

6:00 am - 8:04 amBNA-ORD

2h 04mnonstop

10:55 am - 12:36 pmORD-BNA

1h 41mnonstop

$99United Airlines

Find Deal

Thu, Jan 15 - Sun, Jan 18

6:45 am - 7:10 amSDF-MDW

1h 25mnonstop

9:55 am - 12:10 pmMDW-SDF

1h 15mnonstop

$99Southwest

Find Deal

Wed, Jan 14 - Sat, Jan 17

6:30 am - 7:14 amSDF-ORD

1h 44mnonstop

8:20 pm - 10:56 pmORD-SDF

1h 36mnonstop

$101American Airlines

Find Deal

Wed, Dec 3 - Mon, Dec 8

1:50 pm - 2:05 pmSDF-MDW

1h 15mnonstop

10:05 am - 12:30 pmMDW-SDF

1h 25mnonstop

$101Southwest

Find Deal

Thu, Dec 4 - Mon, Dec 8

9:00 pm - 10:50 pmBNA-ORD

1h 50mnonstop

3:26 pm - 10:27 pmORD-BNA

7h 01m1 stop

$110Spirit Airlines

Find Deal

Wed, Dec 3 - Wed, Dec 10

9:00 pm - 10:50 pmBNA-ORD

1h 50mnonstop

1:34 pm - 10:27 pmORD-BNA

32h 53m2 stops

$131Spirit Airlines

Find Deal

Wed, Dec 3 - Fri, Dec 5

American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

American Airlines

Dec 25

SDF6:27 amLouisville Intl

1h 39m

ORD7:06 amChicago O'Hare Intl

Jan 1

ORD10:53 amChicago O'Hare Intl

1h 37m

SDF1:30 pmLouisville Intl

$97

Find similar

American Airlines

Dec 3

SDF6:30 amLouisville Intl

1h 44m

ORD7:14 amChicago O'Hare Intl

Dec 8

ORD8:20 pmChicago O'Hare Intl

1h 36m

SDF10:56 pmLouisville Intl

$101

Find similar

American Airlines

Dec 3

SDF6:30 amLouisville Intl

1h 44m

ORD7:14 amChicago O'Hare Intl

Dec 9

ORD9:50 amChicago O'Hare Intl

1h 40m

SDF12:30 pmLouisville Intl

$102

Find similar

Frontier flights from Kentucky to Chicago

Our best Frontier deals on Kentucky to Chicago flight tickets

Frontier

Nov 21

BNA8:45 amNashville Intl

1h 53m

ORD10:38 amChicago O'Hare Intl

Nov 24

ORD6:13 amChicago O'Hare Intl

1h 37m

BNA7:50 amNashville Intl

$77

Find similar

Frontier

Nov 24

BNA8:45 amNashville Intl

1h 53m

ORD10:38 amChicago O'Hare Intl

Nov 28

ORD6:13 amChicago O'Hare Intl

1h 37m

BNA7:50 amNashville Intl

$78

Find similar

Frontier

Nov 20

BNA8:46 pmNashville Intl

11h 00m

1 stop

ORD7:46 amChicago O'Hare Intl

Nov 24

ORD6:13 amChicago O'Hare Intl

1h 37m

BNA7:50 amNashville Intl

$84

Find similar

Fly from

Fly to

Route

Depart

Return

Price

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Fri 11/21

8:45 am-10:38 am

Nonstop1h 53m

Chicago O'Hare Intl

Mon 11/24

6:13 am-7:50 am

Nonstop1h 37m

$77

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Mon 11/24

8:45 am-10:38 am

Nonstop1h 53m

Chicago O'Hare Intl

Fri 11/28

6:13 am-7:50 am

Nonstop1h 37m

$78

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Thu 12/25

6:27 am-7:06 am

Nonstop1h 39m

Chicago O'Hare Intl

Thu 1/1

10:53 am-1:30 pm

Nonstop1h 37m

$97

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 1/14

8:29 am-9:13 am

Nonstop1h 44m

Chicago O'Hare Intl

Sat 1/17

5:50 pm-8:28 pm

Nonstop1h 38m

$99

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Thu 1/15

6:00 am-8:04 am

Nonstop2h 04m

Chicago O'Hare Intl

Sun 1/18

10:55 am-12:36 pm

Nonstop1h 41m

$99

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 1/14

6:45 am-7:10 am

Nonstop1h 25m

Chicago Midway

Sat 1/17

9:55 am-12:10 pm

Nonstop1h 15m

$99

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Wed 12/3

6:30 am-7:14 am

Nonstop1h 44m

Chicago O'Hare Intl

Mon 12/8

8:20 pm-10:56 pm

Nonstop1h 36m

$101

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

1:50 pm-2:05 pm

Nonstop1h 15m

Chicago Midway

Mon 12/8

10:05 am-12:30 pm

Nonstop1h 25m

$101

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/3

9:00 pm-10:50 pm

Nonstop1h 50m

Chicago O'Hare Intl

Wed 12/10

3:26 pm-10:27 pm

1 stop7h 01m

$110

NashvilleChicago

BNA - ORD

BNAORD

Nashville Intl

Wed 12/3

9:00 pm-10:50 pm

Nonstop1h 50m

Chicago O'Hare Intl

Fri 12/5

1:34 pm-10:27 pm

2 stops32h 53m

$131

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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 $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 $522. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $891.

What is the cheapest Kentucky to Chicago flight route?

Fly from Louisville Intl 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 $282 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 $189 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	$169
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 $169. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $170.

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 November 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) (19.02% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (14.90%), Embraer 175 (13.41%), and Canadair (Bombardier) Regional Jet (9.61%).

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 11,040 reviews	Search American Airlines flights
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,241 reviews	Search Southwest flights
Contour	PriceFrom $116	Free Cancellation	Rating 7.5 40 reviews	Search Contour flights
United Airlines	PriceFrom $123	Free Cancellation	Rating 7.4 9,007 reviews	Search United Airlines flights

Merrillville

New Buffalo

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 $48

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 11/21. 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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Filter for what you want

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Find the cheapest flights from Kentucky to Chicago

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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

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 $522. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $891.

What is the cheapest Kentucky to Chicago flight route?

Fly from Louisville Intl 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?

Frontier, United Airlines, and Southwest 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 November 2025, 191 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 7:00AM, with 46% of daily flights taking off at noon.

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

As of November 2025, there are 1,340 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Thu, with 17% 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