$79 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 10/24. 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

Mon, Aug 24 - Mon, Aug 31
Southwest Logo
7:05 am - 12:15 pm
CVG
-
MDW
6h 10m
2 stops
Southwest Logo
6:10 pm - 8:25 pm
MDW
-
CVG
1h 15mnonstop
$172Southwest
Sat, Aug 29 - Sat, Aug 29
Southwest Logo
5:50 am - 1:05 pm
CVG
-
MDW
8h 15m
2 stops
Southwest Logo
3:25 pm - 5:35 pm
MDW
-
CVG
1h 10mnonstop
$172Southwest
Thu, Aug 27 - Sat, Aug 29
Delta Logo
10:53 am - 4:17 pm
CVG
-
ORD
6h 24m
1 stop
Delta Logo
5:18 pm - 10:40 pm
ORD
-
CVG
4h 22m
1 stop
$177Delta
Mon, Oct 26 - Thu, Oct 29
Delta Logo
2:18 pm - 6:29 pm
CVG
-
ORD
5h 11m
1 stop
Delta Logo
11:19 am - 5:57 pm
ORD
-
CVG
5h 38m
1 stop
$177Delta
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
7:00 am - 7:34 am
CVG
-
ORD
1h 34mnonstop
United Airlines Logo
9:40 pm - 12:07 am
ORD
-
CVG
1h 27mnonstop
$196United Airlines
Fri, Aug 14 - Mon, Aug 17
United Airlines Logo
11:17 am - 11:52 am
CVG
-
ORD
1h 35mnonstop
United Airlines Logo
9:27 pm - 11:55 pm
ORD
-
CVG
1h 28mnonstop
$196United Airlines
Mon, Aug 24 - Sun, Aug 30
American Airlines Logo
8:30 am - 9:09 am
CVG
-
ORD
1h 39mnonstop
American Airlines Logo
6:55 pm - 9:18 pm
ORD
-
CVG
1h 23mnonstop
$196American Airlines
Sat, Aug 22 - Sun, Aug 23
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
$196American Airlines
Sun, Oct 4 - Wed, Oct 7
Frontier Logo
1:49 pm - 5:38 am
BNA
-
ORD
15h 49m
1 stop
Frontier Logo
6:30 am - 2:18 pm
ORD
-
BNA
7h 48m
1 stop
$224Frontier
Sun, Oct 11 - Wed, Oct 14
Frontier Logo
4:02 pm - 12:24 am
BNA
-
ORD
8h 22m
1 stop
Frontier Logo
6:05 am - 3:07 pm
ORD
-
BNA
9h 02m
1 stop
$224Frontier
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Good to know

Low season

January

Cheapest flight

$79
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 24% lower on average.
Flight from Cincinnati 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
Munster
Schererville
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 $821
Business Class flights to Chicagofrom $946
Premium Economy Class flights to Chicagofrom $462
Economy Class flights to Chicagofrom $157