Cheap flights from Chicago to Kentucky from $38
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Kentucky departing on 9/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to Kentucky
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Spirit Airlines flights from Chicago to Kentucky
Our best Spirit Airlines deals on Chicago to Kentucky flight tickets
American Airlines flights from Chicago to Kentucky
Our best American Airlines deals on Chicago to Kentucky flight tickets
See travel insights to Kentucky from
How to get the cheapest flight ticket from Chicago to Kentucky
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Kentucky?
If you’re not able to fly to Kentucky in August, then May is your next best option. Flight prices from Chicago to Kentucky during May average around $227.
What is the cheapest day to depart on your flight to Kentucky?
Our data shows that Saturday is the least expensive day to fly to Kentucky. Tickets to fly out on this day can be as low as $257. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $508. These prices are subject to change though, so be sure to set up a Price Alert for flights to Kentucky.
What is the cheapest time of day to depart on your flight to Kentucky?
According to our data, the cheapest time of day to fly to Kentucky is in the evening. momondo users have found flights departing from Chicago to Kentucky in the evening for as low as $275. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Kentucky is in the morning when prices are around $307.
What is the cheapest Chicago to Kentucky flight route?
Fly from Chicago Midway to Louisville Intl for the best Chicago - Kentucky flight prices
How far in advance should I book a flight to Kentucky?
You are more likely to see cheaper flights to Kentucky from Chicago when booking 15 weeks ahead of your departure date. In general, you can expect to find flights to Kentucky for around $321 when searching 15 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Kentucky from Chicago for as low as $181 on momondo.
What cabin class options are available on Chicago to Kentucky flights?
There are 4 cabin classes available to choose from on Chicago to Kentucky flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to Kentucky?
Spirit Airlines, United Airlines, and Southwest are the most popular carriers operating from Chicago to Kentucky
What airlines fly to Kentucky?
American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Kentucky from Chicago according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Kentucky. Keep in mind that there are 4 different airlines that fly to Kentucky on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to Kentucky on average per day?
As of June 2025, there are 186 flights per day flying from Chicago to Kentucky. The most common time of day flights depart is 8:00PM, with 36% of flights taking off in the afternoon.
How many flights depart from Chicago to Kentucky on average per week?
1,308 flights are operational weekly from Chicago to Kentucky as of June 2025. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.
Cheap Chicago to Kentucky flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to Kentucky
When did momondo last update prices for flights from Chicago to Kentucky?
Prices for flights from Chicago to Kentucky were last updated today.
How many operators does momondo search for flights from Chicago to Kentucky?
The number of operators available for flights from Chicago to Kentucky is 7 as of June 2025.
How old do you have to be to fly from Chicago to Kentucky?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago to Kentucky.
What documentation or ID do you need to fly to Kentucky?
The travel and health documents required for your trip to Kentucky can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Kentucky. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to Kentucky?
Based on momondo bookings for flights between Chicago and Kentucky, the leading plane model is Embraer 170, making up 18.68% of the total bookings. Other popular models include Embraer 175 (Enhanced Winglets) with 17.69%, Canadair (Bombardier) Regional Jet CRJ-550 with 15.89%, and Embraer 175 with 11.19%.
Best airlines flying from Chicago to Kentucky
Compare and see reviews for airlines that fly from Chicago to Kentucky with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $102 | Free Cancellation | Rating 7.1 26 reviews | |||
| PriceFrom $105 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $119 | Free Cancellation | Rating 7.4 8,790 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 8.0 4,287 reviews |
Why use momondo?
Why should I use momondo to find a flight deal from Chicago to Kentucky?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Kentucky from Chicago.
Can I find flights from Chicago to Kentucky with flexible booking policies on momondo?
momondo does allow users to show only those flights to Kentucky from Chicago which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Chicago to Kentucky?
Once all potential Chicago to Kentucky flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Chicago to Kentucky right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Chicago to Kentucky flights. All you need is a valid email address and we will do the rest; it is that quick and easy.