$38 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 5/29. 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

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 22% 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.

Flights Deals
Useful Info
Flights 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.

Recent round-trip flight deals from Kentucky to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Kentucky to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
3:00 pm - 4:58 pmBNA-ORD
1h 58mnonstop
Frontier Logo
12:35 pm - 2:17 pmORD-BNA
1h 42mnonstop
$79Frontier
Find Deal
Thu, May 29 - Sun, Jun 1
Spirit Airlines Logo
2:28 pm - 4:25 pmBNA-ORD
1h 57mnonstop
Spirit Airlines Logo
5:20 pm - 6:52 pmORD-BNA
1h 32mnonstop
$80Spirit Airlines
Find Deal
Fri, May 16 - Mon, May 19
 Logo
2:28 pm - 4:25 pmBNA-ORD
1h 57mnonstop
 Logo
12:35 pm - 2:17 pmORD-BNA
1h 42mnonstop
Fri, Jun 6 - Sun, Jun 8
Allegiant Air Logo
1:29 pm - 2:03 pmTYS-MDW
1h 34mnonstop
Allegiant Air Logo
2:53 pm - 5:18 pmMDW-TYS
1h 25mnonstop
$90Allegiant Air
Find Deal
Fri, Jun 6 - Fri, Jun 13
 Logo
2:28 pm - 4:25 pmBNA-ORD
1h 57mnonstop
 Logo
12:35 pm - 2:17 pmORD-BNA
1h 42mnonstop
Fri, May 30 - Sun, Jun 1
Allegiant Air Logo
5:37 pm - 6:10 pmTYS-MDW
1h 33mnonstop
Allegiant Air Logo
2:53 pm - 5:18 pmMDW-TYS
1h 25mnonstop
$113Allegiant Air
Find Deal
Mon, Jun 2 - Fri, Jun 6
Southwest Logo
9:25 pm - 11:00 pmBNA-MDW
1h 35mnonstop
Southwest Logo
5:15 am - 6:40 amMDW-BNA
1h 25mnonstop
$145Southwest
Find Deal
Thu, May 29 - Thu, Jun 5
American Airlines Logo
9:57 am - 11:47 amBNA-ORD
1h 50mnonstop
American Airlines Logo
6:51 am - 8:18 amORD-BNA
1h 27mnonstop
$145American Airlines
Find Deal
Fri, Jul 4 - Sun, Jul 6
American Airlines Logo
7:16 pm - 9:09 pmBNA-ORD
1h 53mnonstop
American Airlines Logo
7:10 am - 8:49 amORD-BNA
1h 39mnonstop
$146American Airlines
Find Deal
Thu, May 29 - Mon, Jun 2
Southwest Logo
8:15 am - 9:55 amBNA-MDW
1h 40mnonstop
Southwest Logo
5:45 am - 7:10 amMDW-BNA
1h 25mnonstop
$152Southwest
Find Deal
Wed, Jun 18 - Sun, Jun 22
Useful Info

Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$38
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Nashville 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.

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.