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 31m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

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

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

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

As of August 2026, 207 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 11:00AM, with 61% of daily flights taking off at noon.

What airlines fly to Chicago?

United Airlines, American Airlines and Contour are the top three most popular airlines that fly to Chicago from Kentucky according to our data. United Airlines is the first choice among our users, with 44% 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 many flights depart from Kentucky to Chicago on average per week?

As of August 2026, there are 1,455 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Wed, 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 August 2026, there are 6 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.

$58 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.

8:30 am - 9:09 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 39mnonstop

6:56 am - 9:24 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 28mnonstop

$158American Airlines

Sat, Sep 5 - Sun, Sep 6

7:15 pm - 7:25 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

3:25 pm - 5:40 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 15mnonstop

$163Southwest

Tue, Sep 1 - Sat, Sep 5

2:50 pm - 8:35 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

6h 45m1 stop Baltimore/Washington

8:55 am - 2:00 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

4h 05m1 stop Nashville Intl

$164Southwest

Sat, Sep 5 - Sun, Sep 6

12:26 pm - 7:53 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

20h 27m1 stop Atlanta Hartsfield-Jackson

1:59 pm - 11:21 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

20h 22m1 stop Atlanta Hartsfield-Jackson

$167Frontier

Mon, Aug 31 - Fri, Sep 4

12:48 pm - 8:28 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

8h 40m1 stop Atlanta Hartsfield-Jackson

9:33 pm - 11:43 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

13h 10m1 stop Atlanta Hartsfield-Jackson

$167Frontier

Wed, Oct 21 - Sun, Oct 25

5:25 am - 5:54 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 29mnonstop

6:50 am - 9:16 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$169United Airlines

Thu, Sep 3 - Sun, Sep 6

2:05 pm - 2:39 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

2:30 pm - 5:00 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 30mnonstop

$169United Airlines

Sat, Sep 5 - Tue, Sep 8

8:27 pm - 9:14 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 47mnonstop

4:30 pm - 6:59 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 29mnonstop

$169American Airlines

Sat, Sep 5 - Tue, Sep 8

6:10 am - 9:17 amCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

4h 07m1 stop Detroit Metropolitan Wayne County

9:29 am - 1:28 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

2h 59m1 stop Detroit Metropolitan Wayne County

$177Delta

Mon, Sep 7 - Thu, Sep 10

6:00 pm - 10:44 pmSDF Louisville Intl-MDW Chicago Midway

5h 44m1 stop Atlanta Hartsfield-Jackson

11:35 am - 7:30 pmMDW Chicago Midway-SDF Louisville Intl

6h 55m1 stop Atlanta Hartsfield-Jackson

$203Delta

Sat, Sep 12 - Sat, Sep 19

Cheap last minute flights

Enter your travel dates to find the best prices.

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$228Contour

Mon, Aug 17 - Thu, Aug 20

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$228Contour

Wed, Aug 19 - Sun, Aug 23

12:26 pm - 8:08 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

8h 42m1 stop Atlanta Hartsfield-Jackson

8:55 pm - 6:47 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

8h 52m1 stop Las Vegas Harry Reid Intl

$234Frontier

Tue, Aug 18 - Fri, Sep 18

12:26 pm - 8:08 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

8h 42m1 stop Atlanta Hartsfield-Jackson

7:44 pm - 11:43 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

14h 59m1 stop Atlanta Hartsfield-Jackson

$240Frontier

Wed, Aug 19 - Thu, Oct 8

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

5:59 pm - 10:17 amORD Chicago O'Hare Intl-BNA Nashville Intl

16h 18m1 stop Orlando

$240Multiple Airlines

Wed, Aug 19 - Sat, Aug 29

12:25 pm - 8:52 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

8h 27m1 stop Denver Intl

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$251Multiple Airlines

Sat, Aug 15 - Fri, Aug 21

11:57 am - 12:44 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 47mnonstop

8:56 am - 11:27 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 31mnonstop

$319American Airlines

Sun, Aug 16 - Sun, Aug 23

7:01 pm - 8:02 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

2h 01mnonstop

7:30 am - 12:51 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 21m1 stop Charlotte Douglas

$329American Airlines

Sun, Aug 16 - Sun, Aug 23

9:05 am - 9:10 amCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 05mnonstop

8:05 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 20mnonstop

$330Southwest

Tue, Aug 18 - Fri, Sep 18

5:40 am - 11:35 amCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

6h 55m1 stop Baltimore/Washington

8:05 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 20mnonstop

$340Southwest

Tue, Aug 18 - Fri, Sep 18

Cheap direct flights

Enter your travel dates to find the best prices.

8:30 am - 9:09 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 39mnonstop

6:56 am - 9:24 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 28mnonstop

$158American Airlines

Sat, Sep 5 - Sun, Sep 6

7:15 pm - 7:25 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

3:25 pm - 5:40 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 15mnonstop

$163Southwest

Tue, Sep 1 - Sat, Sep 5

5:25 am - 5:54 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 29mnonstop

6:50 am - 9:16 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$169United Airlines

Thu, Sep 3 - Sun, Sep 6

2:05 pm - 2:39 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

2:30 pm - 5:00 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 30mnonstop

$169United Airlines

Sat, Sep 5 - Tue, Sep 8

8:27 pm - 9:14 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 47mnonstop

4:30 pm - 6:59 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 29mnonstop

$169American Airlines

Sat, Sep 5 - Tue, Sep 8

8:20 am - 8:25 amCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 05mnonstop

4:20 pm - 6:30 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$181Southwest

Sat, Sep 26 - Sat, Oct 3

5:34 am - 6:17 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 43mnonstop

10:15 am - 12:39 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 24mnonstop

$181American Airlines

Sat, Sep 26 - Sat, Oct 17

4:55 pm - 5:05 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

8:05 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 20mnonstop

$181Southwest

Sat, Sep 5 - Mon, Sep 7

11:00 am - 11:42 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 42mnonstop

9:20 pm - 11:56 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 36mnonstop

$183United Airlines

Mon, Sep 14 - Mon, Sep 14

1:58 pm - 2:37 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 39mnonstop

3:27 pm - 5:54 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

1h 27mnonstop

$346Allegiant Air

Wed, Nov 25 - Sun, Nov 29

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American Airlines flights from Kentucky to Chicago

Our best American Airlines deals on Kentucky to Chicago flight tickets

American Airlines

Sep 5

CVG8:30 amCincinnati Cinci./N. Kentucky

1h 39m

ORD9:09 amChicago O'Hare Intl

Sep 6

ORD6:56 amChicago O'Hare Intl

1h 28m

CVG9:24 amCincinnati Cinci./N. Kentucky

$158

American Airlines

Sep 12

SDF5:59 pmLouisville Intl

1h 55m

ORD6:54 pmChicago O'Hare Intl

Sep 14

ORD7:59 pmChicago O'Hare Intl

1h 34m

SDF10:33 pmLouisville Intl

$184

American Airlines

Sep 5

CVG11:03 amCincinnati Cinci./N. Kentucky

1h 41m

ORD11:44 amChicago O'Hare Intl

Sep 7

ORD6:55 pmChicago O'Hare Intl

1h 23m

CVG9:18 pmCincinnati Cinci./N. Kentucky

$193

Contour flights from Kentucky to Chicago

Our best Contour deals on Kentucky to Chicago flight tickets

Contour

Sep 4

BNA8:00 amNashville Intl

3h 40m

1 stop

ORD11:40 amChicago O'Hare Intl

Sep 7

ORD12:30 pmChicago O'Hare Intl

3h 40m

1 stop

BNA4:10 pmNashville Intl

$217

Contour

Aug 27

BNA8:00 amNashville Intl

3h 40m

1 stop

ORD11:40 amChicago O'Hare Intl

Aug 30

ORD12:30 pmChicago O'Hare Intl

3h 40m

1 stop

BNA4:10 pmNashville Intl

$224

Contour

Sep 4

BNA8:00 amNashville Intl

3h 40m

1 stop

ORD11:40 amChicago O'Hare Intl

Sep 7

ORD12:30 pmChicago O'Hare Intl

3h 40m

1 stop

BNA4:10 pmNashville Intl

$228

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 9/5

8:30 am-9:09 am

Nonstop1h 39m

Chicago O'Hare Intl

Sun 9/6

6:56 am-9:24 am

Nonstop1h 28m

$158

Quickest round-trip

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Tue 9/1

7:15 pm-7:25 pm

Nonstop1h 10m

Chicago Midway

Sat 9/5

3:25 pm-5:40 pm

Nonstop1h 15m

$163

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/5

2:50 pm-8:35 pm

1 stop6h 45m

Chicago Midway

Sun 9/6

8:55 am-2:00 pm

1 stop4h 05m

$164

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Mon 8/31

12:26 pm-7:53 am

1 stop20h 27m

Chicago O'Hare Intl

Fri 9/4

1:59 pm-11:21 am

1 stop20h 22m

$167

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Wed 10/21

12:48 pm-8:28 pm

1 stop8h 40m

Chicago O'Hare Intl

Sun 10/25

9:33 pm-11:43 am

1 stop13h 10m

$167

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 9/3

5:25 am-5:54 am

Nonstop1h 29m

Chicago O'Hare Intl

Sun 9/6

6:50 am-9:16 am

Nonstop1h 26m

$169

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 9/5

2:05 pm-2:39 pm

Nonstop1h 34m

Chicago O'Hare Intl

Tue 9/8

2:30 pm-5:00 pm

Nonstop1h 30m

$169

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - ORD Chicago O'Hare Intl

CVGORD

Cincinnati Cinci./N. Kentucky

Sat 9/5

8:27 pm-9:14 pm

Nonstop1h 47m

Chicago O'Hare Intl

Tue 9/8

4:30 pm-6:59 pm

Nonstop1h 29m

$169

CincinnatiChicago

CVG Cincinnati Cinci./N. Kentucky - MDW Chicago Midway

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 9/7

6:10 am-9:17 am

1 stop4h 07m

Chicago Midway

Thu 9/10

9:29 am-1:28 pm

1 stop2h 59m

$177

LouisvilleChicago

SDF Louisville Intl - MDW Chicago Midway

SDFMDW

Louisville Intl

Sat 9/12

6:00 pm-10:44 pm

1 stop5h 44m

Chicago Midway

Sat 9/19

11:35 am-7:30 pm

1 stop6h 55m

$203

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 October is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $232. If you’re not able to fly to Chicago in October, then September is your next best option. Flight prices from Kentucky to Chicago during September average around $251.

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 $487. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Kentucky to Chicago for around $640.

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 $509. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $931.

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 $331 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 $114 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 39% 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	$182
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 $182. The best round-trip flight deal from Kentucky to Chicago found on momondo in the last 72 hours is $164.

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

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 August 2026, there are 6 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 (19.56% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (19.18%), Embraer 175 (13.21%), and Canadair (Bombardier) Regional Jet 700 (10.07%).

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
Southwest	PriceFrom $97	Free Cancellation	Rating 8.0 4,218 reviews	Search Southwest flights
Contour	PriceFrom $104	Free Cancellation	Rating 7.5 43 reviews	Search Contour flights
United Airlines	PriceFrom $117	Free Cancellation	Rating 7.4 10,113 reviews	Search United Airlines flights
American Airlines	PriceFrom $152	Free Cancellation	Rating 7.1 11,925 reviews	Search American Airlines flights

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

Cheap flights from Kentucky to Chicago from $63

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 10/12. 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

Contour flights from Kentucky to Chicago

Our best Contour deals on Kentucky to Chicago flight tickets

momondo Fare Finder

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

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?

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

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

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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.

Popular cities in the United States

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

Fly to other destinations from Kentucky

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