Cheap flights from Kentucky to Chicago from $34
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kentucky to Chicago departing on 5/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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How to get the cheapest flight ticket from Kentucky to Chicago
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 Chicago?
The month of April is, on average, the cheapest month to fly to Chicago from Kentucky, with most prices found around $211. If you’re not able to fly to Chicago in April, then August is your next best option. Flight prices from Kentucky to Chicago during August average around $215.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $505. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Kentucky to Chicago for around $725.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Kentucky to Chicago during this time can be as low as $514. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $952.
What is the cheapest Kentucky to Chicago flight route?
Fly from Owensboro Daviess County to Chicago O'Hare Intl for the best Kentucky - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Kentucky when booking 8 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $271 when searching 8 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Kentucky for as low as $176 on momondo.
What cabin class options are available on Kentucky to Chicago flights?
There are 4 cabin classes available to choose from on Kentucky to Chicago 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 Kentucky to Chicago?
Spirit Airlines, Frontier, and American Airlines are the most popular carriers operating from Kentucky to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Chicago from Kentucky according to our data. American Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Kentucky to Chicago on average per day?
As of April 2025, 191 flights take off from Kentucky and land in Chicago each day. The most common flight departure time for this route is 5:00PM, with 49% of daily flights taking off at noon.
How many flights depart from Kentucky to Chicago on average per week?
As of April 2025, there are 1,341 flights per week flying from Kentucky to Chicago. The most common day of the week flights depart is Wed, with 18% of flights taking off on this day.
Cheap Kentucky to Chicago flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Kentucky to Chicago
When did momondo last update prices for flights from Kentucky to Chicago?
Prices for flights from Kentucky to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from Kentucky to Chicago?
As of April 2025, there are 6 operators available to choose from for flights from Kentucky to Chicago.
How old do you have to be to fly from Kentucky to Chicago?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Kentucky to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Kentucky to Chicago is Embraer 175 (Enhanced Winglets) (17.47% of total bookings). The next most popular plane models are Embraer 170 (15.73%), Canadair (Bombardier) Regional Jet (13.35%), and Canadair (Bombardier) Regional Jet CRJ-550 (12.32%).
Best airlines flying from Kentucky to Chicago
Compare and see reviews for airlines that fly from Kentucky to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $107 | Free Cancellation | Rating 7.4 8,667 reviews | |||
| PriceFrom $114 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $116 | Free Cancellation | Rating 7.1 26 reviews | |||
| PriceFrom $160 | Free Cancellation | Rating 8.0 7,916 reviews | |||
| PriceFrom $172 | Free Cancellation | Rating 8.0 4,280 reviews |
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Kentucky to Chicago?
momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Kentucky to Chicago. momondo saves you time and could save you money on your trip.
Can I find flights from Kentucky to Chicago with flexible booking policies on momondo?
momondo does allow users to show only those flights to Chicago from Kentucky which offer a flexible booking policy as well as other useful filters and features.
How can momondo help me find flights from Kentucky to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kentucky.
I’m not ready to book a flight from Kentucky to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from Kentucky to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.