$62 Find Cheap Flights from Kentucky to Chicago - Compare and Save

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 8/13. 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

Wed, Aug 12 - Fri, Aug 14
Frontier Logo
12:53 pm - 8:02 am
CVG
-
ORD
20h 09m
1 stop
Frontier Logo
1:50 pm - 11:48 am
ORD
-
CVG
20h 58m
1 stop
$179Frontier
Thu, Sep 17 - Sun, Sep 20
Frontier Logo
12:48 pm - 7:44 pm
CVG
-
ORD
7h 56m
1 stop
Frontier Logo
2:03 pm - 11:43 am
ORD
-
CVG
20h 40m
1 stop
$180Frontier
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
6:40 am - 1:20 pm
CVG
-
MDW
7h 40m
2 stops
Southwest Logo
6:30 am - 1:40 pm
MDW
-
CVG
6h 10m
1 stop
$182Southwest
Mon, Sep 21 - Mon, Sep 21
Southwest Logo
6:00 am - 9:30 am
CVG
-
MDW
4h 30m
1 stop
Southwest Logo
6:10 pm - 8:25 pm
MDW
-
CVG
1h 15mnonstop
$186Southwest
Mon, Aug 17 - Thu, Aug 20
Multiple Airlines Logo
9:10 pm - 12:50 pm
SDF
-
ORD
16h 40m
1 stop
Multiple Airlines Logo
8:05 am - 9:49 am
ORD
-
SDF
24h 44m
1 stop
$191Multiple Airlines
Sat, Aug 22 - Mon, Aug 24
Multiple Airlines Logo
12:26 pm - 7:53 am
CVG
-
ORD
20h 27m
1 stop
Multiple Airlines Logo
8:05 am - 7:42 pm
ORD
-
CVG
10h 37m
2 stops
$191Multiple Airlines
Mon, Aug 10 - Tue, Aug 11
American Airlines Logo
9:54 am - 10:35 am
CVG
-
ORD
1h 41mnonstop
American Airlines Logo
6:56 am - 9:24 am
ORD
-
CVG
1h 28mnonstop
$195American Airlines
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
$197Allegiant Air
Sat, Oct 31 - Mon, Nov 2
Allegiant Air Logo
1:52 pm - 10:48 am
TYS
-
MDW
21h 56m
1 stop
Allegiant Air Logo
1:26 pm - 3:51 pm
MDW
-
TYS
1h 25mnonstop
$200Allegiant Air
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
11:05 am - 11:44 am
SDF
-
ORD
1h 39mnonstop
American Airlines Logo
8:05 am - 10:35 am
ORD
-
SDF
1h 30mnonstop
$218American Airlines
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Good to know

Low season

January

Cheapest flight

$62
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Cincinnati to Chicago O'Hare 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
Munster
Chesterton
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 $943
Business Class flights to Chicagofrom $946
Premium Economy Class flights to Chicagofrom $591
Economy Class flights to Chicagofrom $157