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.

$95 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

Mon, Nov 9 - Thu, Nov 12

6:31 pm - 7:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 59mnonstop

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

1h 37mnonstop

$189American Airlines

Fri, Nov 20 - Fri, Nov 27

5:10 am - 5:55 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

4:00 pm - 6:32 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 32mnonstop

$189United Airlines

Mon, Nov 9 - Thu, Nov 12

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

1h 20mnonstop

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

1h 25mnonstop

$191Southwest

Fri, Dec 4 - Sun, Dec 6

7:35 pm - 7:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 25mnonstop

$191Southwest

Sat, Nov 7 - Wed, Nov 11

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, Nov 6 - Tue, Nov 10

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

Mon, Nov 9 - Thu, Nov 12

3:14 pm - 6:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

4h 16m1 stop Detroit Metropolitan Wayne County

1:30 pm - 8:54 pmORD Chicago O'Hare Intl-SDF Louisville Intl

6h 24m1 stop Atlanta Hartsfield-Jackson

$209Delta

Mon, Nov 9 - Thu, Nov 12

3:14 pm - 6:04 pmSDF Louisville Intl-MDW Chicago Midway

3h 50m1 stop Detroit Metropolitan Wayne County

9:30 am - 2:24 pmMDW Chicago Midway-SDF Louisville Intl

3h 54m1 stop Detroit Metropolitan Wayne County

$209Delta

Tue, Nov 24 - Thu, Nov 26

6:30 pm - 7:29 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 59mnonstop

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

1h 34mnonstop

$219American Airlines

Tue, Feb 16 - Thu, Feb 18

6:16 pm - 7:14 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 58mnonstop

6:54 pm - 9:28 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$219American Airlines

Recent last minute flight deals from Kentucky to Chicago

Fri, Oct 30 - Fri, Nov 6

7:10 am - 12:13 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

6h 03m1 stop Atlanta Hartsfield-Jackson

6:30 am - 11:48 amORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 18m1 stop Atlanta Hartsfield-Jackson

$399Delta

Wed, Oct 28 - Wed, Nov 4

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

$408United Airlines

Fri, Oct 30 - Fri, Nov 6

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

$408United Airlines

Tue, Oct 27 - Sun, Nov 1

11:14 am - 11:59 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

9:15 pm - 11:48 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 33mnonstop

$409American Airlines

Fri, Oct 30 - Mon, Nov 2

5:30 am - 6:15 amLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

1h 45mnonstop

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

1h 40mnonstop

$409United Airlines

Tue, Oct 27 - Sun, Nov 1

10:20 am - 4:05 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

6h 45m1 stop Charlotte Douglas

9:15 pm - 11:48 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

1h 33mnonstop

$419American Airlines

Thu, Oct 29 - Fri, Nov 6

4:41 pm - 8:08 pmSDF Louisville Intl-MDW Chicago Midway

28h 27m1 stop Valparaiso Destin-Ft Walton Beach

6:08 am - 8:04 pmMDW Chicago Midway-SDF Louisville Intl

12h 56m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$423Multiple Airlines

Fri, Oct 30 - Sun, Nov 1

1:04 pm - 4:58 pmLEX Lexington Blue Grass-ORD Chicago O'Hare Intl

4h 54m1 stop Atlanta Hartsfield-Jackson

1:23 pm - 7:13 pmORD Chicago O'Hare Intl-LEX Lexington Blue Grass

4h 50m1 stop Atlanta Hartsfield-Jackson

$429Delta

Tue, Oct 27 - Tue, Oct 27

8:35 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

1:05 pm - 3:20 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$537Southwest

Tue, Oct 27 - Wed, Oct 28

8:35 am - 8:50 amSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$537Southwest

Recent direct flight deals from Kentucky to Chicago

Mon, Nov 9 - Thu, Nov 12

6:31 pm - 7:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 59mnonstop

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

1h 37mnonstop

$189American Airlines

Fri, Nov 20 - Fri, Nov 27

5:10 am - 5:55 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 45mnonstop

4:00 pm - 6:32 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 32mnonstop

$189United Airlines

Sat, Dec 5 - Sat, Dec 12

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

1h 15mnonstop

7:55 am - 10:15 amMDW Chicago Midway-SDF Louisville Intl

1h 20mnonstop

$191Southwest

Thu, Nov 12 - Sun, Nov 15

7:55 pm - 8:10 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$191Southwest

Wed, Nov 18 - Wed, Nov 25

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

1h 15mnonstop

7:10 pm - 9:25 pmMDW Chicago Midway-SDF Louisville Intl

1h 15mnonstop

$191Southwest

Fri, Nov 6 - Tue, Nov 10

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

Sat, Nov 7 - Wed, Nov 11

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, Nov 24 - Thu, Nov 26

6:30 pm - 7:29 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 59mnonstop

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

1h 34mnonstop

$219American Airlines

Tue, Feb 16 - Thu, Feb 18

6:16 pm - 7:14 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 58mnonstop

6:54 pm - 9:28 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$219American Airlines

Thu, Nov 12 - Thu, Nov 19

6:31 pm - 7:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 59mnonstop

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

1h 34mnonstop

$219American Airlines

Useful Info

Low season	January
High season	July
Cheapest flight	$95

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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$95 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