$72 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 9/28. 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

Sat, Sep 5 - Sun, Sep 6
American Airlines Logo
9:54 am - 10:35 am
CVG
-
ORD
1h 41mnonstop
American Airlines Logo
10:00 pm - 12:27 am
ORD
-
CVG
1h 27mnonstop
$159American Airlines
Mon, Aug 31 - Wed, Sep 30
Multiple Airlines Logo
10:09 am - 12:50 pm
CVG
-
ORD
27h 41m
2 stops
Multiple Airlines Logo
7:28 pm - 11:38 am
ORD
-
CVG
15h 10m
1 stop
$162Multiple Airlines
Wed, Sep 16 - Wed, Sep 16
Southwest Logo
5:40 am - 9:00 am
CVG
-
MDW
4h 20m
1 stop
Southwest Logo
5:55 pm - 8:15 pm
MDW
-
CVG
1h 20mnonstop
$167Southwest
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
5:25 pm - 8:10 pm
CVG
-
MDW
3h 45m
1 stop
Southwest Logo
6:10 pm - 8:30 pm
MDW
-
CVG
1h 20mnonstop
$167Southwest
Fri, Sep 11 - Fri, Sep 11
American Airlines Logo
5:34 am - 6:17 am
CVG
-
ORD
1h 43mnonstop
American Airlines Logo
6:30 pm - 9:04 pm
ORD
-
CVG
1h 34mnonstop
$167American Airlines
Tue, Aug 25 - Fri, Aug 28
Frontier Logo
12:26 pm - 7:59 pm
CVG
-
ORD
8h 33m
1 stop
Frontier Logo
6:05 am - 1:25 pm
ORD
-
CVG
6h 20m
1 stop
$171Frontier
Mon, Aug 24 - Fri, Aug 28
Frontier Logo
7:15 am - 1:20 pm
CVG
-
ORD
7h 05m
1 stop
Frontier Logo
9:20 am - 6:22 pm
ORD
-
CVG
8h 02m
1 stop
$171Frontier
Tue, Aug 25 - Tue, Aug 25
Delta Logo
6:10 am - 9:17 am
CVG
-
MDW
4h 07m
1 stop
Delta Logo
1:25 pm - 7:54 pm
MDW
-
CVG
5h 29m
1 stop
$177Delta
Tue, Sep 8 - Fri, Sep 11
United Airlines Logo
11:17 am - 11:52 am
CVG
-
ORD
1h 35mnonstop
United Airlines Logo
12:50 pm - 3:23 pm
ORD
-
CVG
1h 33mnonstop
$196United Airlines
Sun, Aug 30 - Thu, Sep 3
United Airlines Logo
2:05 pm - 2:39 pm
CVG
-
ORD
1h 34mnonstop
United Airlines Logo
2:25 pm - 4:55 pm
ORD
-
CVG
1h 30mnonstop
$196United Airlines
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Good to know

Low season

January

Cheapest flight

$72
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 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
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