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.

$98 CHEAP FLIGHTS from Kentucky to Chicago

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Cheap Flights from Kentucky to Chicago

Cheap flights from Kentucky to Chicago with top airlines, updated regularly. Compare round-trip, one-way, direct and last-minute deals.

Round-trip

One-way

Last minute

Direct

Fri, Dec 4 - Fri, Dec 11

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

11:50 am - 1:17 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

$194United Airlines

Sat, Jan 23 - Sat, Feb 20

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

11:59 am - 1:23 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 24mnonstop

$194United Airlines

Wed, Nov 25 - Mon, Nov 30

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

$194United Airlines

Tue, Jan 19 - Thu, Jan 21

10:12 am - 11:00 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

$197American Airlines

Thu, Nov 5 - Mon, Nov 9

4:40 pm - 5:00 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

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

1h 15mnonstop

$197Southwest

Tue, Jan 19 - Thu, Jan 21

8:30 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

8:20 am - 10:45 amMDW Chicago Midway-SDF Louisville Intl

1h 25mnonstop

$197Southwest

Thu, Nov 5 - Mon, Nov 9

10:13 am - 11:00 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 47mnonstop

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

1h 31mnonstop

$198American Airlines

Tue, Jan 19 - Thu, Jan 21

12:53 pm - 6:32 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

6h 39m1 stop Atlanta Hartsfield-Jackson

5:30 am - 11:36 amORD Chicago O'Hare Intl-SDF Louisville Intl

5h 06m1 stop Atlanta Hartsfield-Jackson

$217Delta

Sat, Dec 19 - Sun, Dec 20

10:47 am - 11:30 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 43mnonstop

8:29 am - 11:00 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$241American Airlines

Sat, Nov 21 - Sun, Nov 22

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

3h 37m1 stop Detroit Metropolitan Wayne County

5:30 am - 11:56 amORD Chicago O'Hare Intl-SDF Louisville Intl

5h 26m1 stop Atlanta Hartsfield-Jackson

$251Delta

Sat, Oct 24 - Sat, Oct 31

8:50 am - 9:35 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

10:35 am - 1:13 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 38mnonstop

$379United Airlines

Thu, Oct 22 - Thu, Oct 29

8:50 am - 9:35 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

7:40 am - 10:13 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 33mnonstop

$379United Airlines

Sat, Oct 24 - Wed, Nov 4

5:29 am - 6:08 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 39mnonstop

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

1h 35mnonstop

$385American Airlines

Thu, Oct 22 - Thu, Oct 29

5:29 am - 6:08 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 39mnonstop

6:29 am - 12:25 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 56m1 stop Charlotte Douglas

$389American Airlines

Sat, Oct 24 - Sat, Oct 31

6:58 pm - 7:59 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

2h 01mnonstop

9:02 am - 2:57 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 55m1 stop Charlotte Douglas

$389American Airlines

Sat, Oct 24 - Sat, Oct 31

5:53 pm - 8:30 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

3h 37m1 stop Detroit Metropolitan Wayne County

6:30 am - 12:08 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 38m1 stop Atlanta Hartsfield-Jackson

$399Delta

Fri, Oct 23 - Sun, Oct 25

10:11 am - 10:59 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 48mnonstop

9:30 pm - 11:54 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 24mnonstop

$409United Airlines

Thu, Oct 22 - Mon, Nov 23

9:13 pm - 3:30 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

19h 17m1 stop Fort Lauderdale

4:00 pm - 6:20 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

25h 20m1 stop Fort Lauderdale

$512Multiple Airlines

Wed, Oct 21 - Thu, Oct 22

2:05 pm - 2:20 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

7:55 am - 10:10 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$560Southwest

Tue, Oct 20 - Wed, Oct 21

7:10 pm - 7:25 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

7:50 am - 10:05 amMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$561Southwest

Fri, Mar 12 - Sun, Mar 21

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

1h 46mnonstop

11:59 am - 1:23 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 24mnonstop

$194United Airlines

Wed, Nov 25 - Mon, Nov 30

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

$194United Airlines

Fri, Dec 4 - Fri, Dec 11

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

11:50 am - 1:17 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 27mnonstop

$194United Airlines

Sat, Jan 23 - Sat, Feb 20

5:00 am - 6:29 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 29mnonstop

11:59 am - 1:23 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 24mnonstop

$194United Airlines

Tue, Jan 19 - Thu, Jan 21

10:12 am - 11:00 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

$197American Airlines

Thu, Nov 5 - Mon, Nov 9

4:40 pm - 5:00 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

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

1h 15mnonstop

$197Southwest

Tue, Jan 19 - Thu, Jan 21

8:30 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

8:20 am - 10:45 amMDW Chicago Midway-SDF Louisville Intl

1h 25mnonstop

$197Southwest

Thu, Nov 5 - Mon, Nov 9

10:13 am - 11:00 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 47mnonstop

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

1h 31mnonstop

$198American Airlines

Sat, Nov 21 - Sun, Nov 22

8:20 pm - 8:40 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

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

1h 15mnonstop

$231Southwest

Sat, Dec 19 - Sun, Dec 20

10:47 am - 11:30 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 43mnonstop

8:29 am - 11:00 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$241American Airlines

Low season	January
High season	July
Cheapest flight	$98

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

Most popular time to fly with an average 11% increase in price.

Flight from Owensboro to Chicago

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.