How does KAYAK find such low prices on flights from Kentucky to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kentucky to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kentucky to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Kentucky to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Kentucky with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kentucky to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$94 CHEAP FLIGHTS from Kentucky to Chicago

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Flight Deals

Cheap Flights from Kentucky to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Kentucky to Chicago

Tue, Nov 24 - Tue, Dec 1

10:01 am - 10:49 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

6:54 am - 9:28 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$187American Airlines

Wed, Nov 25 - Wed, Dec 2

10:01 am - 10:49 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

6:59 pm - 9:37 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 38mnonstop

$187American Airlines

Thu, Nov 26 - Thu, Dec 3

7:00 am - 7:45 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

9:20 pm - 11:49 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 29mnonstop

$187United Airlines

Mon, Nov 23 - Thu, Nov 26

10:27 am - 11:12 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

7:05 am - 9:44 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 39mnonstop

$187United Airlines

Thu, Nov 26 - Thu, Dec 3

8:55 am - 9:10 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

8:15 am - 10:30 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$187Southwest

Tue, Nov 24 - Tue, Dec 1

8:35 pm - 9:00 pmSDF Louisville Intl-MDW Chicago Midway

1h 25mnonstop

6:15 pm - 8:35 pmMDW Chicago Midway-SDF Louisville Intl

1h 20mnonstop

$187Southwest

Wed, Nov 18 - Wed, Nov 18

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

2:42 pm - 5:13 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$187American Airlines

Thu, Nov 19 - Mon, Nov 23

9:02 am - 9:45 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 43mnonstop

7:55 pm - 10:30 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 35mnonstop

$187United Airlines

Wed, Nov 25 - Tue, Dec 1

5:40 pm - 8:17 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

3h 37m1 stop Detroit Metropolitan Wayne County

1:34 pm - 9:51 pmORD Chicago O'Hare Intl-SDF Louisville Intl

7h 17m1 stop Atlanta Hartsfield-Jackson

$207Delta

Mon, Nov 23 - Mon, Nov 23

7:50 am - 10:39 amSDF Louisville Intl-ORD Chicago O'Hare Intl

3h 49m1 stop Detroit Metropolitan Wayne County

6:15 pm - 12:10 amORD Chicago O'Hare Intl-SDF Louisville Intl

4h 55m1 stop Atlanta Hartsfield-Jackson

$207Delta

Recent last minute flight deals from Kentucky to Chicago

Thu, Nov 5 - Thu, Nov 12

5:30 am - 6:59 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

12:14 pm - 1:41 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

$284United Airlines

Sat, Oct 31 - Mon, Nov 2

1:50 pm - 2:41 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 51mnonstop

2:50 pm - 5:30 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 40mnonstop

$422United Airlines

Sat, Oct 31 - Mon, Nov 2

9:17 am - 4:05 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

7h 48m1 stop Charlotte Douglas

3:49 pm - 6:24 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 35mnonstop

$432American Airlines

Sat, Oct 31 - Mon, Nov 2

7:45 am - 12:59 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

6h 14m1 stop Detroit Metropolitan Wayne County

5:27 am - 12:08 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

5h 41m1 stop Atlanta Hartsfield-Jackson

$442Delta

Thu, Nov 5 - Sat, Nov 7

10:28 am - 12:59 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

3h 31m1 stop Detroit Metropolitan Wayne County

5:27 am - 12:08 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

5h 41m1 stop Atlanta Hartsfield-Jackson

$467Delta

Thu, Nov 5 - Sat, Nov 7

11:05 am - 11:52 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 47mnonstop

4:30 pm - 7:10 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 40mnonstop

$471United Airlines

Sat, Oct 31 - Mon, Nov 2

9:17 am - 4:05 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

7h 48m1 stop Charlotte Douglas

3:49 pm - 6:24 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 35mnonstop

$484American Airlines

Sat, Oct 31 - Sun, Nov 1

6:21 am - 11:05 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

5h 44m1 stop Charlotte Douglas

3:49 pm - 6:24 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 35mnonstop

$484American Airlines

Sat, Oct 31 - Sun, Nov 1

12:35 pm - 12:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

6:40 pm - 9:00 pmMDW Chicago Midway-SDF Louisville Intl

1h 20mnonstop

$535Southwest

Sat, Oct 31 - Mon, Nov 2

12:35 pm - 12:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

12:50 pm - 3:05 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$535Southwest

Recent direct flight deals from Kentucky to Chicago

Thu, Nov 26 - Thu, Dec 3

8:55 am - 9:10 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

8:15 am - 10:30 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$187Southwest

Tue, Nov 24 - Tue, Dec 1

8:35 pm - 9:00 pmSDF Louisville Intl-MDW Chicago Midway

1h 25mnonstop

6:15 pm - 8:35 pmMDW Chicago Midway-SDF Louisville Intl

1h 20mnonstop

$187Southwest

Tue, Nov 24 - Tue, Dec 1

10:01 am - 10:49 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

6:54 am - 9:28 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$187American Airlines

Wed, Nov 25 - Wed, Dec 2

10:01 am - 10:49 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

6:59 pm - 9:37 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 38mnonstop

$187American Airlines

Thu, Nov 26 - Thu, Dec 3

7:00 am - 7:45 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

9:20 pm - 11:49 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 29mnonstop

$187United Airlines

Mon, Nov 23 - Thu, Nov 26

10:27 am - 11:12 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

7:05 am - 9:44 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 39mnonstop

$187United Airlines

Sat, Dec 12 - Sat, Dec 12

9:10 am - 9:25 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

3:35 pm - 5:50 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$187Southwest

Wed, Nov 25 - Wed, Dec 2

8:25 am - 8:40 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

1:20 pm - 3:35 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$187Southwest

Wed, Nov 18 - Wed, Nov 18

6:27 am - 7:15 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 48mnonstop

2:42 pm - 5:13 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$187American Airlines

Wed, Apr 28 - Fri, May 7

5:00 am - 6:46 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 46mnonstop

12:00 pm - 1:24 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 24mnonstop

$194United Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$94

Best time to beat the crowds with an average 2% drop in price.

Most popular time to fly with an average 10% increase in price.

Flight from Louisville to Chicago O'Hare Airport

How does KAYAK find such low prices on flights from Kentucky to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kentucky to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kentucky to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Kentucky to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Kentucky with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kentucky to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

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$94 Find Cheap Flights from Kentucky to Chicago - Compare and Save

Cheap Flights from Kentucky to Chicago

Recent round-trip flight deals from Kentucky to Chicago

Recent one-way flight deals from Kentucky to Chicago

Recent last minute flight deals from Kentucky to Chicago

Recent direct flight deals from Kentucky to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Kentucky to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Kentucky

Find direct flights for Chicago

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Flights to other popular destinations

Find deals for your return flight