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.

$75 CHEAP FLIGHTS from Kentucky to Chicago

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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, Oct 6 - Sat, Oct 10

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$161Contour

Wed, Oct 7 - Thu, Oct 8

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$177Contour

Fri, Oct 9 - Thu, Oct 15

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

$194United Airlines

Fri, Oct 9 - Tue, Oct 13

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

$194United Airlines

Mon, Dec 7 - Wed, Dec 9

2:05 pm - 2:25 pmSDF Louisville Intl-MDW Chicago Midway

1h 20mnonstop

6:15 pm - 8:30 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$197Southwest

Sat, Dec 5 - Mon, Dec 7

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

1h 15mnonstop

6:15 pm - 8:30 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$197Southwest

Mon, Oct 26 - Mon, Oct 26

12:45 pm - 1:29 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 44mnonstop

6:55 pm - 9:35 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 40mnonstop

$197American Airlines

Thu, Nov 12 - Sat, Nov 14

1:14 pm - 1:57 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 43mnonstop

10:30 am - 1:02 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 32mnonstop

$197American Airlines

Thu, Nov 12 - Sat, Nov 14

7:00 am - 11:50 amSDF Louisville Intl-MDW Chicago Midway

5h 50m1 stop Minneapolis St Paul

5:29 pm - 10:46 pmMDW Chicago Midway-SDF Louisville Intl

4h 17m1 stop Minneapolis St Paul

$217Delta

Thu, Nov 12 - Sat, Nov 14

8:05 am - 11:59 amSDF Louisville Intl-MDW Chicago Midway

4h 54m1 stop Atlanta Hartsfield-Jackson

4:13 pm - 11:13 pmMDW Chicago Midway-SDF Louisville Intl

6h 00m1 stop Atlanta Hartsfield-Jackson

$217Delta

Recent last minute flight deals from Kentucky to Chicago

Mon, Sep 28 - Mon, Oct 5

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$244Contour

Fri, Oct 2 - Tue, Oct 6

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$245Contour

Fri, Oct 2 - Mon, Oct 5

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

1h 45mnonstop

9:20 pm - 11:55 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 35mnonstop

$359United Airlines

Fri, Oct 2 - Fri, Oct 9

6:00 am - 6:45 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

6:50 am - 9:28 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 38mnonstop

$359United Airlines

Fri, Oct 2 - Mon, Oct 5

7:36 am - 12:14 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

5h 38m1 stop Charlotte Douglas

9:35 pm - 12:09 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 34mnonstop

$369American Airlines

Fri, Oct 2 - Fri, Oct 9

11:43 am - 5:38 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

6h 55m1 stop Charlotte Douglas

9:35 pm - 12:09 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 34mnonstop

$369American Airlines

Wed, Sep 30 - Sat, Oct 17

1:15 pm - 4:37 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

4h 22m1 stop Atlanta Hartsfield-Jackson

6:20 am - 11:57 amORD Chicago O'Hare Intl-SDF Louisville Intl

4h 37m1 stop Minneapolis St Paul

$389Delta

Tue, Sep 29 - Sat, Oct 17

1:15 pm - 4:37 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

4h 22m1 stop Atlanta Hartsfield-Jackson

6:20 am - 11:57 amORD Chicago O'Hare Intl-SDF Louisville Intl

4h 37m1 stop Minneapolis St Paul

$389Delta

Tue, Sep 29 - Tue, Oct 6

1:15 pm - 1:30 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

6:00 pm - 8:15 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$517Southwest

Wed, Sep 30 - Wed, Oct 7

6:45 pm - 7:00 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$517Southwest

Recent direct flight deals from Kentucky to Chicago

Tue, Oct 6 - Sat, Oct 10

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$161Contour

Wed, Oct 7 - Thu, Oct 8

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$177Contour

Wed, Oct 7 - Sun, Oct 11

9:00 am - 10:50 amOWB Owensboro Daviess County-ORD Chicago O'Hare Intl

1h 50mnonstop

11:30 am - 1:00 pmORD Chicago O'Hare Intl-OWB Owensboro Daviess County

1h 30mnonstop

$191Contour

Fri, Oct 9 - Thu, Oct 15

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

$194United Airlines

Fri, Oct 9 - Tue, Oct 13

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

$194United Airlines

Thu, Oct 29 - Sun, Nov 1

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

Thu, Oct 15 - Mon, Oct 19

7:50 pm - 8:05 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$197Southwest

Mon, Nov 9 - Mon, Nov 9

8:45 am - 9:00 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$197Southwest

Wed, Oct 28 - Wed, Nov 4

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

$197American Airlines

Thu, Oct 22 - Sat, Oct 24

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

1h 42mnonstop

6:59 am - 9:32 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 33mnonstop

$197American Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$75

Best time to beat the crowds but there is an average 18% increase in price.

Most popular time to fly and prices are also 19% lower on average.

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.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$75 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