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

Thu, Oct 22 - Mon, Oct 26

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

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

1h 27mnonstop

$194United Airlines

Fri, Dec 11 - Sun, Dec 13

2:40 pm - 4:27 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 47mnonstop

9:20 pm - 10:54 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 34mnonstop

$196United Airlines

Fri, Oct 30 - Mon, Nov 2

2:25 pm - 4:15 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

9:30 pm - 11:05 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 35mnonstop

$196United Airlines

Tue, Nov 17 - Tue, Nov 17

8:50 am - 9:05 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 20mnonstop

$197Southwest

Wed, Oct 28 - Thu, Nov 5

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

1h 15mnonstop

6:40 pm - 9:05 pmMDW Chicago Midway-SDF Louisville Intl

1h 25mnonstop

$202Southwest

Wed, Nov 4 - Wed, Nov 11

6:21 am - 7:09 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

$207American Airlines

Thu, Oct 29 - Mon, Nov 2

6:29 am - 7:11 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 42mnonstop

7:08 am - 9:38 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 30mnonstop

$207American Airlines

Tue, Oct 27 - Thu, Oct 29

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

$207Southwest

Sat, Dec 12 - Mon, Dec 14

9:06 am - 3:04 pmSDF Louisville Intl-MDW Chicago Midway

6h 58m1 stop Atlanta Hartsfield-Jackson

5:30 pm - 11:02 pmMDW Chicago Midway-SDF Louisville Intl

4h 32m1 stop Minneapolis St Paul

$217Delta

Thu, Oct 29 - Thu, Nov 5

9:13 pm - 3:37 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

19h 24m1 stop Fort Lauderdale

7:55 am - 5:34 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

8h 39m1 stop Fort Lauderdale

$217Multiple Airlines

Mon, Oct 12 - Wed, Nov 11

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

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

1h 27mnonstop

$244United Airlines

Wed, Oct 14 - Tue, Oct 20

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

$334United Airlines

Sat, Oct 10 - Sat, Oct 17

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

12:02 pm - 1:32 pmORD Chicago O'Hare Intl-PAH Paducah Barkley Regional

1h 30mnonstop

$334United Airlines

Wed, Oct 14 - Wed, Oct 21

11:45 am - 7:31 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

20h 46m1 stop Orlando Sanford Intl

8:46 am - 7:55 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

22h 09m1 stop Orlando

$368Multiple Airlines

Tue, Oct 13 - Tue, Oct 20

8:00 am - 2:20 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

7h 20m1 stop Charlotte Douglas

8:06 am - 10:44 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 38mnonstop

$369American Airlines

Tue, Oct 13 - Wed, Nov 11

6:29 am - 7:11 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 42mnonstop

6:59 pm - 9:36 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 37mnonstop

$374American Airlines

Tue, Oct 13 - Wed, Oct 21

11:20 am - 7:51 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

21h 31m1 stop Orlando Sanford Intl

8:46 am - 7:55 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

22h 09m1 stop Orlando

$379Multiple Airlines

Thu, Oct 15 - Wed, Oct 21

9:20 am - 7:31 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

23h 11m1 stop Orlando Sanford Intl

8:46 am - 7:55 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

22h 09m1 stop Orlando

$392Multiple Airlines

Sat, Oct 10 - Sat, Oct 17

5:05 pm - 5:25 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

4:15 pm - 6:30 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$541Southwest

Sat, Oct 10 - Sat, Oct 10

7:05 am - 9:30 amSDF Louisville Intl-MDW Chicago Midway

3h 25m1 stop Nashville Intl

4:15 pm - 6:30 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$551Southwest

Thu, Oct 22 - Mon, Oct 26

5:00 am - 6:28 amPAH Paducah Barkley Regional-ORD Chicago O'Hare Intl

1h 28mnonstop

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

1h 27mnonstop

$194United Airlines

Fri, Dec 18 - Mon, Dec 21

2:13 pm - 3:59 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 46mnonstop

9:23 pm - 10:59 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 36mnonstop

$196United Airlines

Fri, Dec 11 - Sun, Dec 13

2:40 pm - 4:27 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 47mnonstop

9:20 pm - 10:54 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 34mnonstop

$196United Airlines

Fri, Oct 30 - Mon, Nov 2

2:25 pm - 4:15 pmOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

9:30 pm - 11:05 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 35mnonstop

$196United Airlines

Tue, Nov 17 - Tue, Nov 17

8:50 am - 9:05 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 20mnonstop

$197Southwest

Wed, Oct 28 - Thu, Nov 5

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

1h 15mnonstop

6:40 pm - 9:05 pmMDW Chicago Midway-SDF Louisville Intl

1h 25mnonstop

$202Southwest

Wed, Nov 4 - Wed, Nov 11

6:21 am - 7:09 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

$207American Airlines

Thu, Oct 29 - Mon, Nov 2

6:29 am - 7:11 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 42mnonstop

7:08 am - 9:38 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 30mnonstop

$207American Airlines

Tue, Oct 27 - Thu, Oct 29

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

$207Southwest

Tue, Dec 8 - Sat, Dec 12

6:22 am - 7:09 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 47mnonstop

6:47 am - 9:22 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 35mnonstop

$207American Airlines

Low season	January
High season	July
Cheapest flight	$98

Best time to beat the crowds but there is an average 2% increase in price.

Most popular time to fly with an average 15% 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.