S$207 Cheap Flights from Chicago to Lexington

View S$207 flight on Fri, 3 Oct,2025Opens in a new window

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Cheap Flights from Chicago to Lexington (ORD-LEX)

Prices were available within the past 7 days and start at S$207 for one-way flights and S$388 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, 6 May - Fri, 16 May
ORD
Chicago
LEX
Lexington
S$388 Return, found 2 days ago
S$388
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Fri, 16 May, priced at S$388 found 2 days ago
American Airlines
Tue, 6 May - Thu, 15 May
ORD
Chicago
LEX
Lexington
S$401 Return, found 2 days ago
S$401
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Thu, 15 May, priced at S$401 found 2 days ago
American Airlines
Tue, 6 May - Fri, 16 May
ORD
Chicago
LEX
Lexington
S$420 Return, found 2 days ago
S$420
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Fri, 16 May, priced at S$420 found 2 days ago
United
Tue, 6 May - Fri, 16 May
ORD
Chicago
LEX
Lexington
S$426 Return, found 2 days ago
S$426
Return
found 2 days ago
Select United flight, departing Tue, 6 May from Chicago to Lexington, returning Fri, 16 May, priced at S$426 found 2 days ago
American Airlines
Tue, 6 May - Thu, 15 May
ORD
Chicago
LEX
Lexington
S$433 Return, found 2 days ago
S$433
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Thu, 15 May, priced at S$433 found 2 days ago
American Airlines
Tue, 6 May - Fri, 16 May
ORD
Chicago
LEX
Lexington
S$439 Return, found 2 days ago
S$439
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Fri, 16 May, priced at S$439 found 2 days ago
American Airlines
Fri, 3 Oct - Sun, 5 Oct
ORD
Chicago
LEX
Lexington
S$446 Return, found 7 hours ago
S$446
Return
found 7 hours ago
Select American Airlines flight, departing Fri, 3 Oct from Chicago to Lexington, returning Sun, 5 Oct, priced at S$446 found 7 hours ago
United
Tue, 6 May - Fri, 16 May
ORD
Chicago
LEX
Lexington
S$451 Return, found 2 days ago
S$451
Return
found 2 days ago
Select United flight, departing Tue, 6 May from Chicago to Lexington, returning Fri, 16 May, priced at S$451 found 2 days ago
American Airlines
Tue, 6 May - Thu, 15 May
ORD
Chicago
LEX
Lexington
S$453 Return, found 2 days ago
S$453
Return
found 2 days ago
Select American Airlines flight, departing Tue, 6 May from Chicago to Lexington, returning Thu, 15 May, priced at S$453 found 2 days ago
Delta
Tue, 6 May - Thu, 15 May
ORD
Chicago
LEX
Lexington
S$480 Return, found 2 days ago
S$480
Return
found 2 days ago
Select Delta flight, departing Tue, 6 May from Chicago to Lexington, returning Thu, 15 May, priced at S$480 found 2 days ago
Chicago to Lexington route information
Origin airport
O'Hare Intl.
Destination airport
Blue Grass
Return price
S$387
Distance
517 km

Flights from Chicago to Lexington

When looking for plane tickets from Chicago to Lexington, the ease and convenience of using Expedia simply can’t be beat. With tons of departure points and flights options from the top airline carriers, Expedia gives you the widest array of cheap flights to Lexington. Look for ORD to LEX airfare with the assurance that you have the largest online travel agency working for you.

Expedia lets you search across the largest number of airlines and Lexington flights, which means that you’ll be able to find a great flight deal at the perfect travel date and time. Our simple-to-use booking engine makes looking for terrific bargains easy and hassle-free; just enter your travel dates and departure city, and let Expedia do the rest! Adjust your travel dates and explore connecting flights to find an even better deal on your Chicago Lexington flight!

Browse through dozens of options and rest assured that you’re seeing the best price guaranteed! Our friendly customer service representatives are here to serve you 24 hours day to provide assistance and answer any questions that you may have about booking your Chicago to Lexington trip. There’s simply no substitute for great prices suited to your travel needs and backed by excellent customer support.

Combine your Lexington flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from Chicago to Lexington with Expedia. Use us as your stop travel destination and have the confidence that you’re getting a bargain!

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$388. 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.
*Available to Expedia members.