$49 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 4/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Useful Info
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, Apr 1 - Wed, Apr 8
American Airlines Logo
12:07 pm - 12:41 pm
SDF
-
ORD
1h 34mnonstop
American Airlines Logo
1:34 pm - 4:05 pm
ORD
-
SDF
1h 31mnonstop
$97American Airlines
Tue, Apr 14 - Sat, Apr 18
United Airlines Logo
5:48 pm - 6:40 pm
SDF
-
ORD
1h 52mnonstop
United Airlines Logo
9:30 pm - 11:59 pm
ORD
-
SDF
1h 29mnonstop
$127United Airlines
Tue, Apr 14 - Sat, Apr 18
Southwest Logo
7:00 am - 12:50 pm
SDF
-
ORD
6h 50m
1 stop
Southwest Logo
1:55 pm - 8:50 pm
ORD
-
SDF
5h 55m
1 stop
$152Southwest
Wed, Apr 1 - Wed, Apr 8
Delta Logo
6:00 am - 9:59 am
SDF
-
ORD
4h 59m
1 stop
Delta Logo
11:10 am - 6:49 pm
ORD
-
SDF
6h 39m
1 stop
$157Delta
Wed, Apr 1 - Wed, Apr 8
Delta Logo
7:45 am - 12:29 pm
SDF
-
MDW
5h 44m
1 stop
Delta Logo
10:45 am - 6:49 pm
MDW
-
SDF
7h 04m
1 stop
$157Delta
Wed, Apr 8 - Sat, Apr 11
Southwest Logo
6:15 am - 10:40 am
CVG
-
MDW
5h 25m
1 stop
Southwest Logo
7:40 am - 9:45 am
MDW
-
CVG
1h 05mnonstop
$174Southwest
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
5:20 pm - 1:00 pm
CVG
-
ORD
20h 40m
1 stop
Multiple Airlines Logo
5:01 am - 6:36 pm
ORD
-
CVG
12h 35m
1 stop
$177Multiple Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
12:20 pm - 10:44 pm
CVG
-
ORD
11h 24m
1 stop
Multiple Airlines Logo
11:28 am - 5:33 pm
ORD
-
CVG
5h 05m
1 stop
$178Multiple Airlines
Mon, Apr 27 - Fri, May 1
Frontier Logo
7:46 pm - 7:31 pm
CVG
-
MDW
24h 45m
1 stop
Frontier Logo
3:29 pm - 1:44 pm
MDW
-
CVG
21h 15m
2 stops
$180Frontier
Mon, Mar 30 - Wed, May 6
Frontier Logo
3:57 pm - 8:23 am
CVG
-
ORD
17h 26m
2 stops
Frontier Logo
4:28 pm - 6:36 pm
ORD
-
CVG
25h 08m
1 stop
$180Frontier
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Louisville 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
Chesterton
Schererville
Munster
Porter
Monticello
Griffith
Saint John

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 $392
Business Class flights to Chicagofrom $356
Premium Economy Class flights to Chicagofrom $436
Economy Class flights to Chicagofrom $104