$60 Find Cheap Flights from Kentucky to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 7/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Kentucky to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kentucky to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kentucky to Chicago

Thu, Jul 30 - Sun, Aug 2
Allegiant Air Logo
1:22 pm - 1:58 pm
TYS
-
MDW
1h 36mnonstop
Allegiant Air Logo
2:48 pm - 5:18 pm
MDW
-
TYS
1h 30mnonstop
$149Allegiant Air
Thu, Aug 6 - Sun, Aug 9
Allegiant Air Logo
1:23 pm - 1:59 pm
TYS
-
MDW
1h 36mnonstop
Allegiant Air Logo
2:49 pm - 5:19 pm
MDW
-
TYS
1h 30mnonstop
$171Allegiant Air
Tue, Aug 4 - Tue, Aug 11
United Airlines Logo
5:50 pm - 6:40 pm
SDF
-
ORD
1h 50mnonstop
United Airlines Logo
4:30 pm - 7:07 pm
ORD
-
SDF
1h 37mnonstop
$177United Airlines
Wed, Aug 26 - Wed, Aug 26
Southwest Logo
1:15 pm - 1:30 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
6:20 pm - 8:35 pm
MDW
-
SDF
1h 15mnonstop
$177Southwest
Wed, Aug 26 - Wed, Aug 26
Southwest Logo
1:15 pm - 1:30 pm
SDF
-
MDW
1h 15mnonstop
Southwest Logo
3:05 pm - 9:30 pm
MDW
-
SDF
5h 25m
1 stop
$187Southwest
Mon, Jul 6 - Wed, Jul 8
Frontier Logo
12:53 pm - 7:53 am
CVG
-
ORD
20h 00m
1 stop
Frontier Logo
1:50 pm - 11:13 am
ORD
-
CVG
20h 23m
1 stop
$191Frontier
Wed, Aug 26 - Sat, Aug 29
United Airlines Logo
12:29 pm - 1:03 pm
CVG
-
ORD
1h 34mnonstop
United Airlines Logo
4:38 pm - 7:12 pm
ORD
-
CVG
1h 34mnonstop
$195United Airlines
Sat, Aug 8 - Wed, Aug 12
American Airlines Logo
10:23 am - 11:02 am
SDF
-
ORD
1h 39mnonstop
American Airlines Logo
6:50 pm - 9:25 pm
ORD
-
SDF
1h 35mnonstop
$196American Airlines
Fri, Jul 3 - Tue, Jul 7
Frontier Logo
12:54 pm - 8:03 am
CVG
-
ORD
20h 09m
1 stop
Frontier Logo
1:50 pm - 11:48 am
ORD
-
CVG
20h 58m
1 stop
$208Frontier
Wed, Aug 26 - Fri, Aug 28
American Airlines Logo
5:00 am - 7:08 am
BNA
-
ORD
2h 08mnonstop
American Airlines Logo
4:53 pm - 9:12 pm
ORD
-
BNA
4h 19m
1 stop
$239American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$60
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Knoxville to Chicago Midway Airport

FAQs for booking flights from Kentucky 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Schererville
Chesterton
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Kentucky

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights to Chicagofrom $458
Business Class flights to Chicagofrom $594
Premium Economy Class flights to Chicagofrom $613
Economy Class flights to Chicagofrom $118