$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 12/25. 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
$90
Typical prices: $143-$325
Spirit Airlines
Wed 12/3Sat 12/6
BNA - ORD • Non-stop
Cheapest non-stop
$97
Typical prices: $275-$556
United Airlines
Wed 12/24Wed 12/31
SDF - ORD • Non-stop
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Flight Deals
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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

Wed, Dec 3 - Sat, Dec 6
Spirit Airlines Logo
9:00 pm - 10:50 pmBNA-ORD
1h 50mnonstop
Spirit Airlines Logo
3:26 pm - 10:27 pmORD-BNA
7h 01m1 stop
$90Spirit Airlines
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Wed, Dec 24 - Wed, Dec 31
United Airlines Logo
5:40 am - 6:24 amSDF-ORD
1h 44mnonstop
United Airlines Logo
10:35 am - 1:13 pmORD-SDF
1h 38mnonstop
$97United Airlines
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Mon, Nov 24 - Mon, Dec 15
Frontier Logo
8:45 am - 10:38 amBNA-ORD
1h 53mnonstop
Frontier Logo
7:00 am - 6:46 pmORD-BNA
11h 46m1 stop
$104Frontier
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Wed, Jan 14 - Sat, Jan 17
American Airlines Logo
8:07 am - 9:00 amSDF-ORD
1h 53mnonstop
American Airlines Logo
9:55 am - 12:26 pmORD-SDF
1h 31mnonstop
$107American Airlines
Find Deal
Thu, Dec 25 - Thu, Jan 1
American Airlines Logo
8:05 am - 8:45 amSDF-ORD
1h 40mnonstop
American Airlines Logo
8:53 pm - 11:30 pmORD-SDF
1h 37mnonstop
$109American Airlines
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Sun, Nov 23 - Mon, Dec 1
Frontier Logo
1:34 pm - 11:11 amBNA-ORD
21h 37m1 stop
Frontier Logo
6:13 am - 7:50 amORD-BNA
1h 37mnonstop
$114Frontier
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Mon, Nov 24 - Fri, Nov 28
Multiple Airlines Logo
3:28 pm - 11:06 pmBNA-ORD
7h 38m1 stop
Multiple Airlines Logo
6:13 am - 7:50 amORD-BNA
1h 37mnonstop
$115Multiple Airlines
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Wed, Dec 3 - Wed, Dec 17
Southwest Logo
8:55 pm - 10:35 pmBNA-MDW
1h 40mnonstop
Southwest Logo
6:20 pm - 7:55 pmMDW-BNA
1h 35mnonstop
$117Southwest
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Thu, Nov 27 - Fri, Nov 28
Multiple Airlines Logo
2:47 pm - 11:13 pmBNA-ORD
8h 26m1 stop
Multiple Airlines Logo
6:13 am - 7:50 amORD-BNA
1h 37mnonstop
$120Multiple Airlines
Find Deal
Wed, Dec 3 - Wed, Dec 17
Southwest Logo
1:10 pm - 4:35 pmBNA-MDW
3h 25m1 stop
Southwest Logo
12:25 pm - 1:55 pmMDW-BNA
1h 30mnonstop
$123Southwest
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Useful Info

Good to know

Low seasonJanuary
Cheapest flight$49
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% increase in price.
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
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 $531
Business Class flights to Chicagofrom $745
Prem Econ Class flights to Chicagofrom $773
Economy Class flights to Chicagofrom $148