$59 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 1/7. 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

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Everything you should know

Cheapest round-trip
$117
Overall average: $263
Southwest
Wed 1/7Wed 1/14
BNA - MDW • Non-stop
Cheapest one-way
$59
Typical prices: $184-$295
Southwest
Wed 1/7
BNA - MDW • 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

Wed, Jan 7 - Wed, Jan 14
Southwest Logo
4:25 pm - 6:05 pm
BNA
-
MDW
1h 40mnonstop
Southwest Logo
7:45 pm - 9:15 pm
MDW
-
BNA
1h 30mnonstop
$117Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
10:20 am - 12:15 pm
BNA
-
ORD
1h 55mnonstop
Southwest Logo
1:45 pm - 3:20 pm
ORD
-
BNA
1h 35mnonstop
$117Southwest
Wed, Jan 7 - Wed, Jan 14
Southwest Logo
4:25 pm - 6:05 pm
BNA
-
MDW
1h 40mnonstop
Southwest Logo
3:00 pm - 7:35 pm
MDW
-
BNA
4h 35m1 stop
$127Southwest
Sat, Jan 24 - Sun, Jan 25
Frontier Logo
10:00 am - 4:35 pm
CVG
-
ORD
7h 35m1 stop
Frontier Logo
6:41 am - 8:19 pm
ORD
-
CVG
12h 38m1 stop
$128Frontier
Sun, Feb 22 - Tue, Feb 24
Multiple Airlines Logo
11:03 am - 9:16 am
CVG
-
ORD
23h 13m1 stop
Multiple Airlines Logo
7:00 am - 7:32 pm
ORD
-
CVG
11h 32m1 stop
$138Multiple Airlines
Thu, Jan 8 - Sun, Jan 11
Multiple Airlines Logo
8:40 am - 8:30 pm
BNA
-
ORD
11h 50m1 stop
Multiple Airlines Logo
7:30 am - 7:25 am
ORD
-
BNA
23h 55m1 stop
$139Multiple Airlines
Thu, Jan 8 - Fri, Jan 23
Frontier Logo
6:10 am - 6:45 pm
CVG
-
ORD
13h 35m1 stop
Frontier Logo
5:40 am - 11:55 am
ORD
-
CVG
5h 15m1 stop
$145Frontier
Thu, Jan 8 - Tue, Jan 20
United Airlines Logo
5:35 am - 6:19 am
SDF
-
ORD
1h 44mnonstop
United Airlines Logo
7:52 pm - 10:30 pm
ORD
-
SDF
1h 38mnonstop
$171United Airlines
Sun, Jan 18 - Mon, Jan 19
United Airlines Logo
6:12 pm - 6:55 pm
SDF
-
ORD
1h 43mnonstop
United Airlines Logo
10:45 am - 1:24 pm
ORD
-
SDF
1h 39mnonstop
$173United Airlines
Thu, Jan 8 - Mon, Jan 12
Spirit Airlines Logo
7:00 am - 9:03 pm
SDF
-
ORD
15h 03m1 stop
Spirit Airlines Logo
8:43 pm - 2:41 pm
ORD
-
SDF
16h 58m1 stop
$187Spirit Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$59
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Nashville 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
Chesterton
Schererville
Munster
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 $490
Business Class flights to Chicagofrom $482
Prem Econ Class flights to Chicagofrom $465
Economy Class flights to Chicagofrom $100