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.

$63 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

Thu, Oct 1 - Thu, Oct 15

5:30 am - 5:59 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 29mnonstop

9:41 pm - 11:59 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 18mnonstop

$157United Airlines

Mon, Sep 14 - Thu, Sep 17

9:56 am - 10:29 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 33mnonstop

6:59 am - 9:25 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$157United Airlines

Mon, Sep 21 - Tue, Sep 22

7:51 am - 8:28 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 37mnonstop

8:15 am - 10:48 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 33mnonstop

$157American Airlines

Thu, Sep 17 - Mon, Sep 21

5:34 am - 6:17 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 43mnonstop

6:53 am - 9:26 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 33mnonstop

$157American Airlines

Thu, Sep 17 - Thu, Sep 24

7:00 pm - 7:10 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

8:05 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 20mnonstop

$157Southwest

Sat, Oct 3 - Sat, Oct 10

5:50 pm - 6:00 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

8:15 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Tue, Sep 29 - Thu, Oct 1

8:56 pm - 10:59 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

27h 03m1 stop Orlando

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

7h 01m1 stop Orlando

$158Frontier

Thu, Oct 15 - Tue, Oct 20

8:19 pm - 7:02 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

23h 43m1 stop Orlando

6:00 am - 11:38 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

4h 38m1 stop Atlanta Hartsfield-Jackson

$158Frontier

Fri, Sep 25 - Mon, Sep 28

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

$211Contour

Thu, Sep 24 - 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

$211Contour

Recent last minute flight deals from Kentucky to Chicago

Fri, Aug 28 - Wed, Sep 30

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

3h 40m1 stop Quincy Regional

6:30 am - 2:18 pmORD Chicago O'Hare Intl-BNA Nashville Intl

7h 48m1 stop Denver Intl

$240Multiple Airlines

Thu, Aug 27 - Fri, Aug 28

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

$248Contour

Fri, Aug 28 - Sun, Sep 27

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

$248Contour

Sat, Aug 29 - Wed, Sep 30

5:05 pm - 11:08 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

6h 03m1 stop Orlando

3:50 pm - 4:45 pmORD Chicago O'Hare Intl-BNA Nashville Intl

24h 55m1 stop Orlando

$255Frontier

Wed, Aug 26 - Wed, Sep 30

5:05 pm - 11:08 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

6h 03m1 stop Orlando

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

16h 58m1 stop Orlando

$262Frontier

Sat, Aug 29 - Wed, Sep 2

5:05 pm - 11:08 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

6h 03m1 stop Orlando

11:15 am - 4:10 pmORD Chicago O'Hare Intl-BNA Nashville Intl

4h 55m1 stop Quincy Regional

$264Multiple Airlines

Wed, Aug 26 - Wed, Sep 30

3:25 pm - 4:55 pmBNA Nashville Intl-MDW Chicago Midway

1h 30mnonstop

5:20 pm - 6:50 pmMDW Chicago Midway-BNA Nashville Intl

1h 30mnonstop

$340Southwest

Sat, Aug 29 - Wed, Sep 30

5:15 am - 6:50 amBNA Nashville Intl-MDW Chicago Midway

1h 35mnonstop

8:55 am - 10:30 amMDW Chicago Midway-BNA Nashville Intl

1h 35mnonstop

$340Southwest

Wed, Aug 26 - Wed, Sep 30

5:54 pm - 8:05 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

2h 11mnonstop

8:06 am - 9:54 amORD Chicago O'Hare Intl-BNA Nashville Intl

1h 48mnonstop

$340American Airlines

Fri, Aug 28 - Sun, Aug 30

7:34 am - 8:45 amTYS Knoxville McGhee Tyson-ORD Chicago O'Hare Intl

2h 11mnonstop

8:14 am - 11:06 amORD Chicago O'Hare Intl-TYS Knoxville McGhee Tyson

1h 52mnonstop

$349American Airlines

Recent direct flight deals from Kentucky to Chicago

Thu, Sep 17 - Thu, Sep 24

7:00 pm - 7:10 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

8:05 am - 10:25 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 20mnonstop

$157Southwest

Mon, Sep 14 - Tue, Sep 15

7:00 pm - 7:10 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 10mnonstop

12:45 pm - 2:55 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Mon, Sep 14 - Thu, Sep 17

12:17 pm - 12:51 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

8:40 am - 11:06 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$157United Airlines

Wed, Sep 16 - Thu, Sep 17

11:17 am - 11:52 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 35mnonstop

7:59 pm - 10:32 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 33mnonstop

$157United Airlines

Thu, Sep 24 - Thu, Sep 24

2:18 pm - 3:00 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 42mnonstop

9:30 pm - 11:52 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 22mnonstop

$157American Airlines

Thu, Sep 17 - Mon, Sep 21

5:34 am - 6:17 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 43mnonstop

6:53 am - 9:26 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 33mnonstop

$157American Airlines

Sat, Sep 26 - Sat, Sep 26

8:20 am - 8:25 amCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

1h 05mnonstop

3:25 pm - 5:40 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 15mnonstop

$157Southwest

Wed, Sep 16 - Tue, Sep 22

2:21 pm - 2:55 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

7:59 pm - 10:32 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 33mnonstop

$157United 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

$266Allegiant Air

Wed, Nov 25 - Sun, Nov 29

1:58 pm - 2:37 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 39mnonstop

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

1h 27mnonstop

$328Allegiant Air

Useful Info

Low season	January
High season	October
Cheapest flight	$63

Best time to beat the crowds but there is an average 16% increase in price.

Most popular time to fly and prices are also 22% 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

Saint Joseph

Hammond

Portage

Lansing

Valparaiso

Chesterton

Munster

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

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Complete your trip

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Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Kentucky

First Class flights to Chicagofrom $794

Business Class flights to Chicagofrom $786

Premium Economy Class flights to Chicagofrom $462

Economy Class flights to Chicagofrom $158

$63 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?

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Kentucky

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

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Chicago

Choose which airport to fly into in Chicago

Find deals for your return flight