S$280 Cheap Flights from Chicago to Lexington

View S$280 flight on Fri, 15 Aug, 2025Opens in a new window

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)

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Cheap Flights from Chicago to Lexington (ORD-LEX)

Prices were available within the past 7 days and start at S$280 for one-way flights and S$267 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$267 Return, found 18 hours ago
S$267
Return
found 18 hours ago
Select Delta flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$267 found 18 hours ago
Delta
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$306 Return, found 18 hours ago
S$306
Return
found 18 hours ago
Select Delta flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$306 found 18 hours ago
American Airlines
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$319 Return, found 18 hours ago
S$319
Return
found 18 hours ago
Select American Airlines flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$319 found 18 hours ago
United
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$319 Return, found 18 hours ago
S$319
Return
found 18 hours ago
Select United flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$319 found 18 hours ago
American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
LEX
Lexington
S$320 Return, found 5 days ago
S$320
Return
found 5 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Lexington, returning Sun, 17 Aug, priced at S$320 found 5 days ago
American Airlines
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$357 Return, found 18 hours ago
S$357
Return
found 18 hours ago
Select American Airlines flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$357 found 18 hours ago
American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
LEX
Lexington
S$362 Return, found 5 days ago
S$362
Return
found 5 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Lexington, returning Sun, 17 Aug, priced at S$362 found 5 days ago
American Airlines
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$370 Return, found 18 hours ago
S$370
Return
found 18 hours ago
Select American Airlines flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$370 found 18 hours ago
American Airlines
Sun, 10 Aug - Sun, 17 Aug
ORD
Chicago
LEX
Lexington
S$371 Return, found 5 days ago
S$371
Return
found 5 days ago
Select American Airlines flight, departing Sun, 10 Aug from Chicago to Lexington, returning Sun, 17 Aug, priced at S$371 found 5 days ago
American Airlines
Fri, 15 Aug - Fri, 22 Aug
ORD
Chicago
LEX
Lexington
S$374 Return, found 18 hours ago
S$374
Return
found 18 hours ago
Select American Airlines flight, departing Fri, 15 Aug from Chicago to Lexington, returning Fri, 22 Aug, priced at S$374 found 18 hours ago

Find the cheapest month to fly from Chicago (ORD) to Lexington (LEX)

November is typically the cheapest month to fly

From S$157 - S$547 per traveller.

Graph displaying average flight prices per month

Chicago to Lexington route information
Origin airport
O'Hare Intl.
Destination airport
Blue Grass
Airlines serving
American Airlines, Delta, United
Return price
S$266
Distance
517 km
Average flight time
2 hours 32 mins

Perfect flights from Chicago to Lexington

Your Journey from Chicago to Lexington

Start your unforgettable journey with Expedia. Our broad selection of flights from Chicago to Lexington caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta, American Airlines, United. Our selection of flights from O'Hare Intl. to Blue Grass caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Chicago to Lexington Flights

Experience the joy of finding cheap flights from O'Hare Intl. to Blue Grass that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$280 and roundtrip prices from S$267*.
 

Pre-Flight Essentials

Ensure a smooth journey from Chicago to Lexington with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Lexington

Picture yourself stepping off the plane in Lexington and immersing yourself in the unique atmosphere of Lexington. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Chicago to Lexington Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Chicago to Lexington.
 

Beyond the Flight – Exploring Lexington

With Expedia, your adventure extends beyond the flight. Explore Lexington at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Chicago to Lexington with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Chicago to Lexington with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from O'Hare Airport to LEX?
Pack your bags, because round-trip flights from O'Hare Airport to Blue Grass Airport start from S$267. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can change quickly, so book today to nab the best deal. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from ORD to Blue Grass Airport (LEX)?
The majority of flights can be cancelled online, but whether or not you are charged a fee differs between airlines. If you do need to cancel your break, follow the easy instructions in the Customer Service Portal.
How do I find cheap flights from O'Hare Airport to Blue Grass Airport (LEX) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for ORD to Blue Grass Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from O'Hare Airport to LEX?
That movie you've been desperate to see will just have to wait --- the flight distance between ORD (ORD) and Blue Grass Airport (LEX) is only 520 kilometres. The captain will be instructing you to buckle up for landing before you know it.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Blue Grass Airport?
Many adventurers opt to fly with United Airlines (UA) from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX). This popular airline offers 95 monthly flights, so you can easily find a flight time that works for you. After some more options? Check out the ticket prices from American Airlines (AA). This carrier offers 60 flights every month between these destinations.
Are O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) flight tickets cheaper when they're purchased at the last minute?
Last-minute planners can sometimes nab a bargain, with some super cheap fares from O'Hare Airport to Blue Grass Airport (LEX) arising a few weeks before the date of departure. If you'd rather plan ahead of time, Expedia compares and updates all the best flight deals continuously --- as early as a year in advance in some cases. It depends on the carrier though, as not all airlines publish prices so far in advance.

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