Cheap flights from Kentucky to Chicago 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 Kentucky to Chicago departing on 7/18. 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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United Airlines flights from Kentucky to Chicago O'Hare Intl Airport
Our best United Airlines deals on Kentucky to Chicago O'Hare Intl Airport flight tickets
Southwest flights from Kentucky to Chicago O'Hare Intl Airport
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How to get the cheapest flight ticket from Kentucky to Chicago O'Hare Intl Airport
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 O'Hare Intl Airport?
The month of October is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Kentucky averaging around $235.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Thursday when prices can be found for as low as $532. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Kentucky because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $829.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Kentucky in the morning is the least expensive time of day to depart. momondo users have found prices as low as $544 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $1,090. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Kentucky to Chicago O'Hare Intl flight route?
Fly from Owensboro Daviess County to Chicago O'Hare Intl for the best Kentucky - Chicago O'Hare Intl flight prices
How far in advance should I book a flight to Chicago O'Hare Intl Airport?
You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $285 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Kentucky for as low as $165 on momondo.
What cabin class options are available on Kentucky to Chicago O'Hare Intl flights?
There are 4 cabin classes available to choose from on Kentucky to Chicago O'Hare Intl 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 O'Hare Intl?
Spirit Airlines, United Airlines, and American Airlines are the most popular carriers operating from Kentucky to Chicago O'Hare Intl
What airlines fly to Chicago O'Hare Intl Airport?
American Airlines, United Airlines and Contour are the top three most popular airlines that fly to Chicago O'Hare Intl Airport from Kentucky according to our data. American Airlines is the first choice among our users, with 51% of people opting to fly with this airline when traveling to Chicago O'Hare Intl Airport. Keep in mind that there are 3 different airlines that fly to Chicago O'Hare Intl Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Kentucky to Chicago O'Hare Intl Airport on average per day?
As of June 2025, there are 202 flights per day flying from Kentucky to Chicago O'Hare Intl Airport. The most common time of day flights depart is 2:00PM, with 51% of flights taking off at noon.
How many flights depart from Kentucky to Chicago O'Hare Intl Airport on average per week?
1,414 flights are operational weekly from Kentucky to Chicago O'Hare Intl Airport as of June 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.
Cheap Kentucky to Chicago O'Hare Intl Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Kentucky to Chicago O'Hare Intl Airport
When did momondo last update prices for flights from Kentucky to Chicago O'Hare Intl Airport?
Prices for flights from Kentucky to Chicago O'Hare Intl Airport refresh daily.
How many operators does momondo search for flights from Kentucky to Chicago O'Hare Intl Airport?
As of June 2025, there are 6 operators available to choose from for flights from Kentucky to Chicago O'Hare Intl Airport.
How old do you have to be to fly from Kentucky to Chicago O'Hare Intl Airport?
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 O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The travel and health documents required for your trip to Chicago O'Hare Intl Airport 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 Chicago O'Hare Intl Airport. 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 Kentucky to Chicago O'Hare Intl Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Kentucky to Chicago O'Hare Intl Airport is Embraer 175 (Enhanced Winglets) (20.97% of total bookings). The next most popular plane models are Canadair (Bombardier) Regional Jet CRJ-550 (16.06%), Embraer 170 (14.62%), and Canadair (Bombardier) Regional Jet 700 (10.14%).
Best airlines flying from Kentucky to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Kentucky to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $105 | Free Cancellation | Rating 7.4 8,810 reviews | |||
| PriceFrom $111 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $113 | Free Cancellation | Rating 7.0 27 reviews |
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Why should I use momondo to find a flight deal from Kentucky to Chicago?
It is quick and easy to find Kentucky to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Kentucky to Chicago with flexible booking policies on momondo?
Flights from Kentucky to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Kentucky to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Kentucky. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Kentucky to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Kentucky. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.