$159 Cheap Flights from Chicago (ORD) to Lexington (LEX)

View $159 flight on Thu, Oct 30, 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 $159 for one-way flights and $189 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, Sep 13 - Mon, Sep 15
ORD
Chicago
LEX
Lexington
$189 Roundtrip, just found
$189
Roundtrip
just found
Select American Airlines flight, departing Sat, Sep 13 from Chicago to Lexington, returning Mon, Sep 15, priced at $189 just found
United
Fri, Aug 22 - Sun, Aug 24
ORD
Chicago
LEX
Lexington
$194 Roundtrip, found 10 hours ago
$194
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Aug 22 from Chicago to Lexington, returning Sun, Aug 24, priced at $194 found 10 hours ago
American Airlines
Fri, Aug 1 - Sun, Aug 3
ORD
Chicago
LEX
Lexington
$194 Roundtrip, found 1 hour ago
$194
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Aug 1 from Chicago to Lexington, returning Sun, Aug 3, priced at $194 found 1 hour ago
United
Fri, Aug 22 - Sun, Aug 24
ORD
Chicago
LEX
Lexington
$199 Roundtrip, found 10 hours ago
$199
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Aug 22 from Chicago to Lexington, returning Sun, Aug 24, priced at $199 found 10 hours ago
United
Fri, Jul 25 - Mon, Jul 28
ORD
Chicago
LEX
Lexington
$199 Roundtrip, found 14 hours ago
$199
Roundtrip
found 14 hours ago
Select United flight, departing Fri, Jul 25 from Chicago to Lexington, returning Mon, Jul 28, priced at $199 found 14 hours ago
United
Tue, Jul 22 - Tue, Jul 29
ORD
Chicago
LEX
Lexington
$202 Roundtrip, found 3 days ago
$202
Roundtrip
found 3 days ago
Select United flight, departing Tue, Jul 22 from Chicago to Lexington, returning Tue, Jul 29, priced at $202 found 3 days ago
American Airlines
Tue, Oct 14 - Tue, Oct 21
ORD
Chicago
LEX
Lexington
$202 Roundtrip, found 2 hours ago
$202
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Oct 14 from Chicago to Lexington, returning Tue, Oct 21, priced at $202 found 2 hours ago
United
Thu, Jul 31 - Sun, Aug 3
ORD
Chicago
LEX
Lexington
$207 Roundtrip, found 2 hours ago
$207
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Jul 31 from Chicago to Lexington, returning Sun, Aug 3, priced at $207 found 2 hours ago
United
Fri, Jul 25 - Mon, Jul 28
ORD
Chicago
LEX
Lexington
$208 Roundtrip, found 14 hours ago
$208
Roundtrip
found 14 hours ago
Select United flight, departing Fri, Jul 25 from Chicago to Lexington, returning Mon, Jul 28, priced at $208 found 14 hours ago
Delta
Sat, Aug 9 - Fri, Aug 22
ORD
Chicago
LEX
Lexington
$209 Roundtrip, found 3 hours ago
$209
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Aug 9 from Chicago to Lexington, returning Fri, Aug 22, priced at $209 found 3 hours ago

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

November is typically the cheapest month to fly

From $123 - $427 per traveler.

Graph displaying average flight prices per month

Alternative airports near Lexington

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Blue Grass LEX. Cheapest and Closest option available. Average driving time to city center is 9 minutes. Flights from $271
LEX
Blue Grass
CheapestClosest
Average driving time to city center9 min
Flights from $271
Flights from Chicago (ORD) to Lexington (LEX)
Origin airport
O'Hare Intl.
Destination airport
Blue Grass
Airlines serving
American Airlines, Delta, United
Roundtrip price
$189
Distance
323 mi
Average flight time
2 hours 31 mins

Chicago to Lexington Flights

The cheapest times to fly from Chicago to Lexington

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Lexington are during the month of September. You can find some of the cheapest flights from Chicago to Lexington with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Lexington

Sunday is one of the best days to book for cheap flights from Chicago to Lexington: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Lexington

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Lexington in 2025. You can also book with separate airlines for your outbound and return journeys, from $159 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Lexington flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Lexington airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) cost?
You can find affordable return tickets from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) starting at $189. Reserve your seat and take off on your trip. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a United flight leaving ORD on August 1 2025 and touching down at LEX. The price was last updated on July 8 2025 and has not changed since.
What is the cheapest month to fly from ORD to LEX?
The cheapest flights from ORD to LEX are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
You can travel nonstop from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) on a United Airlines flight.
What is the cheapest airline that flies from ORD to LEX?
Fly from ORD to LEX with United. This airline currently offers the cheapest one-way ticket for this route, starting at $214. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from ORD on October 1 2025. Prices were last updated on July 8 2025 and have not changed since.
How many flights per day from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
Each day on average, 4 nonstop flights operate from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX). Choose the departure that best fits your schedule.
What are the most popular departure times for flights from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
The 10 AM departures from ORD to LEX see the highest demand. Greater demand means you'll likely pay more for these departures. If you want to save on your fare, choose a less crowded time to fly.
What day of the week has the most flights from ORD to LEX?
Travel on a Sunday if you're looking for the best choice of flights from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX).
What is the earliest flight from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
Hop on the earliest flight at around 10:30AM UTC-6, heading out of O'Hare Intl. Airport (ORD). You'll be traveling for approximately 1h 30m, reaching Blue Grass Airport (LEX) at approximately 1:00PM UTC-5.
How long does it take to fly from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
It takes approximately 1 hour and 29 minutes to travel the 320 mi from ORD to LEX.
What airline has the least delays from ORD to LEX?
With 80% of flights usually arriving as scheduled, American Airlines has the best on-time performance for nonstop flights from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX). To monitor your flight status and get notified about any changes, simply head to the Expedia App.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
To avoid possible delays on the O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) route, aim to travel before 3 PM. Later departures are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Lexington from O'Hare Intl. Airport (ORD)?
If you're boarding a direct flight from O'Hare Intl. Airport (ORD) to Lexington, Blue Grass Airport (LEX) is the only airport you can land at.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX) last-minute?
Holding off until just before your departure to book your flight from ORD to LEX generally means paying more. While you might find some last-minute offers, there's no guarantee. Keep your travel plans flexible for a better chance of getting a bargain.
Is it cheaper to book an ORD to LEX flight and hotel package?
Compared with arranging flights and hotels separately, booking an ORD to LEX flight and hotel package with Expedia could lead to significant savings. Better still, managing everything in one place will take the hassle out of travel planning. Simply pick your flights and choose from our extensive range of stays, then customize your trip with other add-ons like activities and car rentals.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Blue Grass Airport (LEX)?
In most instances, you can cancel or reschedule your ORD to LEX flight. However, additional charges may apply, especially if you booked over 24 hours ago. Check your itinerary for the airline's rules and fees on flight changes, or if you want further details, go to our Customer Service portal.

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