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.

$52 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, Sep 5 - Sun, Sep 6

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

1h 05mnonstop

9:30 am - 11:40 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Sat, Sep 5 - Sun, Sep 6

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

1h 05mnonstop

6:30 pm - 8:40 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Sat, Sep 5 - Sun, Sep 6

9:54 am - 10:35 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 41mnonstop

10:00 pm - 12:27 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 27mnonstop

$157American Airlines

Sat, Sep 5 - Sun, Sep 6

4:15 pm - 4:52 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 37mnonstop

4:38 pm - 7:12 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 34mnonstop

$157United Airlines

Sat, Sep 5 - Sun, Sep 6

8:27 pm - 9:14 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 47mnonstop

10:00 pm - 12:27 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 27mnonstop

$158American Airlines

Thu, Sep 17 - Thu, Sep 17

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

6h 40m1 stop Atlanta Hartsfield-Jackson

8:55 pm - 6:47 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

8h 52m1 stop Las Vegas Harry Reid Intl

$175Frontier

Wed, Oct 28 - Sat, Oct 31

12:48 pm - 7:44 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

7h 56m1 stop Atlanta Hartsfield-Jackson

11:06 am - 8:29 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

8h 23m1 stop Denver Intl

$180Frontier

Sat, Sep 5 - Mon, Sep 7

2:05 pm - 2:39 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

10:43 am - 1:09 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$181United Airlines

Tue, Nov 10 - Thu, Nov 26

2:10 pm - 6:04 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

4h 54m1 stop Detroit Metropolitan Wayne County

9:30 am - 3:17 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

4h 47m1 stop Detroit Metropolitan Wayne County

$201Delta

Thu, Nov 12 - Thu, Nov 26

3:50 pm - 6:04 pmCVG Cincinnati Cinci./N. Kentucky-MDW Chicago Midway

3h 14m1 stop Detroit Metropolitan Wayne County

1:22 pm - 7:10 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

4h 48m1 stop Detroit Metropolitan Wayne County

$201Delta

Recent last minute flight deals from Kentucky to Chicago

Wed, Aug 12 - Wed, Aug 19

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

3h 40m1 stop Quincy Regional

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

4h 55m1 stop Quincy Regional

$228Contour

Wed, Aug 12 - Thu, Aug 13

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

$229Contour

Sun, Aug 9 - Thu, Aug 13

1:23 pm - 1:59 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 36mnonstop

2:49 pm - 5:19 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

1h 30mnonstop

$239Allegiant Air

Sun, Aug 9 - Sun, Aug 16

1:23 pm - 1:59 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 36mnonstop

2:49 pm - 5:19 pmMDW Chicago Midway-TYS Knoxville McGhee Tyson

1h 30mnonstop

$242Allegiant Air

Tue, Aug 11 - Wed, Aug 12

12:25 pm - 8:52 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

8h 27m1 stop Denver Intl

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

4h 55m1 stop Quincy Regional

$252Multiple Airlines

Tue, Aug 11 - Thu, Aug 13

12:25 pm - 8:52 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

8h 27m1 stop Denver Intl

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

3h 40m1 stop Quincy Regional

$252Multiple Airlines

Tue, Aug 11 - Tue, Aug 18

12:25 pm - 8:52 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

8h 27m1 stop Denver Intl

5:59 pm - 4:05 pmORD Chicago O'Hare Intl-BNA Nashville Intl

22h 06m1 stop Orlando

$268Frontier

Wed, Aug 12 - Wed, Aug 19

12:25 pm - 8:52 pmBNA Nashville Intl-ORD Chicago O'Hare Intl

8h 27m1 stop Denver Intl

5:59 pm - 4:05 pmORD Chicago O'Hare Intl-BNA Nashville Intl

22h 06m1 stop Orlando

$280Frontier

Wed, Aug 12 - Thu, Aug 20

1:21 pm - 2:23 pmTYS Knoxville McGhee Tyson-ORD Chicago O'Hare Intl

2h 02mnonstop

8:18 am - 11:10 amORD Chicago O'Hare Intl-TYS Knoxville McGhee Tyson

1h 52mnonstop

$299American Airlines

Wed, Aug 12 - Thu, Aug 13

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

2h 11mnonstop

11:20 am - 12:56 pmORD Chicago O'Hare Intl-BNA Nashville Intl

1h 36mnonstop

$305American Airlines

Recent direct flight deals from Kentucky to Chicago

Sat, Sep 5 - Sun, Sep 6

9:54 am - 10:35 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 41mnonstop

10:00 pm - 12:27 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 27mnonstop

$157American Airlines

Sat, Sep 5 - Sun, Sep 6

4:15 pm - 4:52 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 37mnonstop

4:38 pm - 7:12 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 34mnonstop

$157United Airlines

Sat, Sep 5 - Sun, Sep 6

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

1h 05mnonstop

9:30 am - 11:40 amMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Sat, Sep 5 - Sun, Sep 6

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

1h 05mnonstop

6:30 pm - 8:40 pmMDW Chicago Midway-CVG Cincinnati Cinci./N. Kentucky

1h 10mnonstop

$157Southwest

Sat, Sep 5 - Sun, Sep 6

8:27 pm - 9:14 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 47mnonstop

10:00 pm - 12:27 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 27mnonstop

$158American Airlines

Sat, Sep 5 - Sun, Sep 6

8:30 am - 9:09 amCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 39mnonstop

6:56 am - 9:24 amORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 28mnonstop

$158American Airlines

Sat, Sep 5 - Mon, Sep 7

2:05 pm - 2:39 pmCVG Cincinnati Cinci./N. Kentucky-ORD Chicago O'Hare Intl

1h 34mnonstop

10:43 am - 1:09 pmORD Chicago O'Hare Intl-CVG Cincinnati Cinci./N. Kentucky

1h 26mnonstop

$181United Airlines

Sat, Sep 5 - Sun, Sep 6

9:00 am - 9:41 amSDF Louisville Intl-ORD Chicago O'Hare Intl

1h 41mnonstop

6:56 am - 9:38 amORD Chicago O'Hare Intl-SDF Louisville Intl

1h 42mnonstop

$217United Airlines

Fri, Nov 20 - Sun, Nov 29

1:01 pm - 1:40 pmTYS Knoxville McGhee Tyson-MDW Chicago Midway

1h 39mnonstop

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

1h 27mnonstop

$244Allegiant 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

$264Allegiant Air

Useful Info

Low season	January
High season	October
Cheapest flight	$52

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

Most popular time to fly and prices are also 21% 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

Munster

Chesterton

Schererville

Porter

Monticello

Saint John

Griffith

Everything you need to know for your flight to Chicago

Cabin class

Complete your trip

Direct Flights

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 $946

Premium Economy Class flights to Chicagofrom $462

Economy Class flights to Chicagofrom $158

$52 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