$54 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 7/23. 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

Thu, Aug 6 - Sun, Aug 9
Allegiant Air Logo
1:23 pm - 1:59 pm
TYS
-
MDW
1h 36mnonstop
Allegiant Air Logo
2:49 pm - 5:19 pm
MDW
-
TYS
1h 30mnonstop
$155Allegiant Air
Sun, Jul 12 - Sun, Jul 19
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
$159Allegiant Air
Tue, Jul 14 - Tue, Jul 21
Southwest Logo
7:00 am - 1:35 pm
CVG
-
MDW
7h 35m
2 stops
Southwest Logo
5:20 pm - 9:55 pm
MDW
-
CVG
3h 35m
1 stop
$182Southwest
Sat, Aug 8 - Mon, Aug 10
Southwest Logo
4:55 pm - 5:05 pm
CVG
-
MDW
1h 10mnonstop
Southwest Logo
3:20 pm - 9:35 pm
MDW
-
CVG
5h 15m
1 stop
$186Southwest
Mon, Aug 17 - Thu, Aug 20
Multiple Airlines Logo
2:30 pm - 1:00 pm
CVG
-
ORD
23h 30m
1 stop
Multiple Airlines Logo
8:05 am - 9:32 pm
ORD
-
CVG
12h 27m
1 stop
$186Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
6:00 am - 6:36 am
CVG
-
ORD
1h 36mnonstop
American Airlines Logo
10:00 pm - 12:27 am
ORD
-
CVG
1h 27mnonstop
$194American Airlines
Sat, Sep 26 - Sat, Oct 17
United Airlines Logo
7:00 am - 7:34 am
CVG
-
ORD
1h 34mnonstop
United Airlines Logo
4:20 pm - 6:56 pm
ORD
-
CVG
1h 36mnonstop
$195United Airlines
Mon, Aug 17 - Sun, Aug 23
Multiple Airlines Logo
9:10 pm - 1:00 pm
SDF
-
ORD
16h 50m
1 stop
Multiple Airlines Logo
8:05 am - 9:49 am
ORD
-
SDF
24h 44m
1 stop
$200Multiple Airlines
Tue, Jul 21 - Thu, Jul 23
United Airlines Logo
7:00 am - 7:34 am
CVG
-
ORD
1h 34mnonstop
United Airlines Logo
9:20 pm - 11:52 pm
ORD
-
CVG
1h 32mnonstop
$215United Airlines
Sat, Aug 8 - Mon, Aug 10
American Airlines Logo
10:23 am - 11:02 am
SDF
-
ORD
1h 39mnonstop
American Airlines Logo
6:50 pm - 9:25 pm
ORD
-
SDF
1h 35mnonstop
$246American Airlines
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Good to know

Low seasonJanuary
Cheapest flight$54
Best time to beat the crowds but there is an average 25% increase in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Knoxville 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
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 $452
Business Class flights to Chicagofrom $476
Premium Economy Class flights to Chicagofrom $613
Economy Class flights to Chicagofrom $118