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.

$56 CHEAP FLIGHTS from Kentucky to Chicago

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

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

Sat, Oct 3 - Tue, Oct 6

12:43 pm - 6:23 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

6h 40m1 stop Atlanta Hartsfield-Jackson

7:28 pm - 11:38 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

15h 10m1 stop Atlanta Hartsfield-Jackson

$164Frontier

Tue, Oct 13 - Wed, Oct 14

12:43 pm - 6:31 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

6h 48m1 stop Atlanta Hartsfield-Jackson

7:44 pm - 7:50 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

11h 06m1 stop Atlanta Hartsfield-Jackson

$165Frontier

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

Tue, Oct 20 - Tue, Oct 27

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

1h 42mnonstop

9:39 am - 12:10 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$197American Airlines

Wed, Oct 21 - Thu, Oct 22

1:50 pm - 2:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 40mnonstop

6:55 am - 9:34 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 39mnonstop

$197United Airlines

Thu, Oct 1 - Mon, Oct 5

7:00 am - 7:40 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 40mnonstop

9:25 pm - 11:59 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$197United Airlines

Mon, Nov 9 - Thu, Nov 12

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

Thu, Oct 8 - Thu, Oct 15

3:35 pm - 3:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$197Southwest

Mon, Sep 28 - Wed, Sep 30

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$216Contour

Thu, Dec 3 - Sun, Dec 6

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$220Contour

Recent last minute flight deals from Kentucky to Chicago

Fri, Sep 18 - Wed, Sep 23

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$222Contour

Wed, Sep 16 - Wed, Sep 23

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$222Contour

Wed, Sep 16 - Fri, Sep 25

8:00 am - 11:40 amBNA Nashville Intl-ORD Chicago O'Hare Intl

3h 40m1 stop Quincy Regional

3:50 pm - 8:48 amORD Chicago O'Hare Intl-BNA Nashville Intl

16h 58m1 stop Orlando

$255Multiple Airlines

Fri, Sep 18 - Mon, Sep 21

7:08 pm - 12:45 amBNA Nashville Intl-ORD Chicago O'Hare Intl

5h 37m1 stop Dallas/Fort Worth

12:30 pm - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

3h 40m1 stop Quincy Regional

$269Multiple Airlines

Sun, Sep 20 - Thu, Sep 24

8:56 pm - 10:20 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

14h 24m1 stop Orlando

3:50 pm - 7:36 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

26h 46m1 stop Orlando

$280Frontier

Wed, Sep 16 - Thu, Sep 17

5:16 pm - 12:23 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

8h 07m1 stop Denver Intl

3:50 pm - 11:51 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

7h 01m1 stop Orlando

$300Frontier

Fri, Sep 18 - Sun, Oct 18

8:15 pm - 9:30 pmTYS Knoxville McGhee Tyson-ORD Chicago O'Hare Intl

2h 15mnonstop

8:20 am - 11:05 amORD Chicago O'Hare Intl-TYS Knoxville McGhee Tyson

1h 45mnonstop

$324American Airlines

Fri, Sep 18 - Sun, Oct 18

3:53 pm - 7:38 pmTYS Knoxville McGhee Tyson-ORD Chicago O'Hare Intl

4h 45m1 stop Charlotte Douglas

8:20 am - 11:05 amORD Chicago O'Hare Intl-TYS Knoxville McGhee Tyson

1h 45mnonstop

$334American Airlines

Tue, Sep 15 - Mon, Oct 19

1:55 pm - 7:15 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

6h 20m1 stop Dallas Love Field

6:30 pm - 10:45 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

3h 15m1 stop Nashville Intl

$339Southwest

Tue, Sep 15 - Mon, Oct 19

8:05 am - 3:25 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

8h 20m2 stops Baltimore/Washington Atlanta Hartsfield-Jackson

6:30 pm - 10:45 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

3h 15m1 stop Nashville Intl

$344Southwest

Recent direct flight deals from Kentucky to Chicago

Mon, Nov 9 - Thu, Nov 12

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

Thu, Oct 8 - Thu, Oct 15

3:35 pm - 3:50 pmSDF Louisville Intl-MDW Chicago Midway

1h 15mnonstop

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

1h 15mnonstop

$197Southwest

Sat, Oct 24 - Mon, Oct 26

5:19 pm - 6:14 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 55mnonstop

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

1h 40mnonstop

$197American Airlines

Mon, Oct 5 - Wed, Oct 7

6:14 am - 6:56 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 42mnonstop

9:39 am - 12:10 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 31mnonstop

$197American Airlines

Wed, Oct 21 - Thu, Oct 22

1:50 pm - 2:30 pmSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 40mnonstop

6:55 am - 9:34 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 39mnonstop

$197United Airlines

Thu, Oct 1 - Mon, Oct 5

7:00 am - 7:40 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 40mnonstop

9:25 pm - 11:59 pmORD Chicago O'Hare Intl-SDF Louisville Intl

1h 34mnonstop

$197United Airlines

Mon, Nov 23 - Sun, Nov 29

8:00 am - 8:39 amTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 39mnonstop

3:27 pm - 5:54 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

1h 27mnonstop

$267Allegiant Air

Mon, Nov 23 - Sun, Nov 29

8:00 am - 8:39 amTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 39mnonstop

3:27 pm - 5:54 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

1h 27mnonstop

$270Allegiant Air

Sat, Oct 17 - Mon, Oct 19

5:18 am - 7:19 amBNA Nashville Intl-ORD Chicago O'Hare Intl

2h 01mnonstop

6:59 am - 8:40 amORD Chicago O'Hare Intl-BNA Nashville Intl

1h 41mnonstop

$330Alaska Airlines

Tue, Oct 27 - Tue, Nov 3

6:56 am - 9:00 amBNA Nashville Intl-ORD Chicago O'Hare Intl

2h 04mnonstop

6:59 am - 8:40 amORD Chicago O'Hare Intl-BNA Nashville Intl

1h 41mnonstop

$331Alaska Airlines

Useful Info

Low season	January
High season	October
Cheapest flight	$56

Best time to beat the crowds but there is an average 14% increase in price.

Most popular time to fly and prices are also 24% lower on average.

Flight from Knoxville to Chicago Midway 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

Schererville

Chesterton

Porter

Monticello

Saint John

Griffith

More options for your flight to Chicago

Add a hotel or car rental

Cabin class

Direct Flights

Origins

Other airports

Other destinations

Return flight

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

Car rentals in Chicago

$56 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