$64 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 2/25. 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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Everything you should know

Cheapest round-trip
$174
Overall average: $386
Spirit Airlines
Sat 3/7Mon 3/9
SDF - ORD • 1 stop
Cheapest non-stop
$177
Typical prices: $190-$335
American Airlines
Tue 4/7Tue 4/7
SDF - ORD • Non-stop
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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

Sat, Mar 7 - Mon, Mar 9
Spirit Airlines Logo
12:00 pm - 9:13 pm
SDF
-
ORD
10h 13m
1 stop
Spirit Airlines Logo
8:16 pm - 2:38 pm
ORD
-
SDF
17h 22m
1 stop
$174Spirit Airlines
Fri, Apr 17 - Sun, Apr 19
Delta Logo
7:30 am - 12:43 pm
LEX
-
MDW
6h 13m
1 stop
Delta Logo
6:00 am - 11:46 am
MDW
-
LEX
4h 46m
1 stop
$177Delta
Tue, Apr 7 - Tue, Apr 7
American Airlines Logo
11:13 am - 11:53 am
SDF
-
ORD
1h 40mnonstop
American Airlines Logo
4:04 pm - 6:37 pm
ORD
-
SDF
1h 33mnonstop
$177American Airlines
Tue, Apr 7 - Tue, Apr 7
Southwest Logo
8:55 am - 9:15 am
SDF
-
MDW
1h 20mnonstop
Southwest Logo
6:20 pm - 8:35 pm
MDW
-
SDF
1h 15mnonstop
$177Southwest
Mon, Mar 23 - Wed, Apr 15
Multiple Airlines Logo
9:13 pm - 10:36 am
SDF
-
ORD
14h 23m
1 stop
Multiple Airlines Logo
1:27 pm - 2:38 pm
ORD
-
SDF
24h 11m
1 stop
$179Multiple Airlines
Sat, Mar 7 - Mon, Mar 9
American Airlines Logo
6:10 am - 6:52 am
SDF
-
ORD
1h 42mnonstop
American Airlines Logo
9:05 am - 11:30 am
ORD
-
SDF
1h 25mnonstop
$181American Airlines
Tue, Apr 7 - Tue, Apr 7
Southwest Logo
8:55 am - 9:15 am
SDF
-
MDW
1h 20mnonstop
Southwest Logo
4:50 pm - 9:05 pm
MDW
-
SDF
3h 15m
1 stop
$187Southwest
Sat, Apr 18 - Tue, Apr 21
United Airlines Logo
7:00 am - 7:55 am
TYS
-
ORD
1h 55mnonstop
United Airlines Logo
7:15 am - 10:08 am
ORD
-
TYS
1h 53mnonstop
$189United Airlines
Sat, Feb 21 - Wed, Feb 25
Multiple Airlines Logo
8:30 am - 7:50 pm
BNA
-
ORD
11h 20m
1 stop
Multiple Airlines Logo
8:16 pm - 12:10 pm
ORD
-
BNA
15h 54m
1 stop
$194Multiple Airlines
Thu, Apr 9 - Tue, Apr 14
United Airlines Logo
9:07 am - 9:47 am
SDF
-
ORD
1h 40mnonstop
United Airlines Logo
9:15 pm - 11:46 pm
ORD
-
SDF
1h 31mnonstop
$196United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds but there is an average 22% increase in price.
Most popular time to fly and prices are also 8% 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
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 $359
Business Class flights to Chicagofrom $356
Premium Economy Class flights to Chicagofrom $436
Economy Class flights to Chicagofrom $104