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Cheap Flights to Jessamine County from $141

View $141 flight on Sat, Sep 5, 2026Opens in a new window

Popular airlines to Jessamine County

  • Delta

  • American Airlines

  • United

  • Southwest Airlines

  • Alaska Airlines

  • Lufthansa

  • Breeze Airways

How much is the cheapest flight to Jessamine County?

Prices were available within the past 7 days and start at $141 for one-way flights and $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Sep 9 - Fri, Sep 18
ORD
Chicago
LEX
Lexington
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 9 from Chicago to Lexington, returning Fri, Sep 18, priced at $249 just found
United
Sat, Aug 29 - Mon, Aug 31
ORD
Chicago
LEX
Lexington
$258 Roundtrip, found 5 hours ago
$258
Roundtrip
found 5 hours ago
Select United flight, departing Sat, Aug 29 from Chicago to Lexington, returning Mon, Aug 31, priced at $258 found 5 hours ago
American Airlines
Wed, Sep 9 - Fri, Sep 18
ORD
Chicago
LEX
Lexington
$259 Roundtrip, just found
$259
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep 9 from Chicago to Lexington, returning Fri, Sep 18, priced at $259 just found
United
Fri, Jul 17 - Sat, Jul 18
ORD
Chicago
LEX
Lexington
$261 Roundtrip, found 3 days ago
$261
Roundtrip
found 3 days ago
Select United flight, departing Fri, Jul 17 from Chicago to Lexington, returning Sat, Jul 18, priced at $261 found 3 days ago
United
Thu, Oct 29 - Sun, Nov 1
ORD
Chicago
LEX
Lexington
$262 Roundtrip, found 2 hours ago
$262
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Oct 29 from Chicago to Lexington, returning Sun, Nov 1, priced at $262 found 2 hours ago
United
Sat, Jul 18 - Sat, Aug 1
ORD
Chicago
LEX
Lexington
$264 Roundtrip, found 2 hours ago
$264
Roundtrip
found 2 hours ago
Select United flight, departing Sat, Jul 18 from Chicago to Lexington, returning Sat, Aug 1, priced at $264 found 2 hours ago
Delta
Fri, Aug 7 - Mon, Aug 10
MDW
Chicago
LEX
Lexington
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Delta flight, departing Fri, Aug 7 from Chicago to Lexington, returning Mon, Aug 10, priced at $269 just found
Delta
Wed, Sep 9 - Fri, Sep 18
ORD
Chicago
LEX
Lexington
$269 Roundtrip, just found
$269
Roundtrip
just found
Select Delta flight, departing Wed, Sep 9 from Chicago to Lexington, returning Fri, Sep 18, priced at $269 just found
United
Fri, Jan 8 - Sun, Jan 10
ORD
Chicago
LEX
Lexington
$271 Roundtrip, found 3 hours ago
$271
Roundtrip
found 3 hours ago
Select United flight, departing Fri, Jan 8 from Chicago to Lexington, returning Sun, Jan 10, priced at $271 found 3 hours ago
Alaska Airlines
Tue, Nov 10 - Thu, Nov 12
PAE
Seattle
LEX
Lexington
$593 Roundtrip, found 11 hours ago
$593
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Tue, Nov 10 from Seattle to Lexington, returning Thu, Nov 12, priced at $593 found 11 hours ago

Trending flights to Jessamine County

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jul 28 - Fri, Aug 7
ORD
Chicago
LEX
Lexington
$249 Roundtrip, just found
$249
Roundtrip
just found
Select American Airlines flight, departing Tue, Jul 28 from Chicago to Lexington, returning Fri, Aug 7, priced at $249 just found

Frequently asked questions

How do I find cheap flights to Jessamine County that have flexible change policies?
It's as easy as 1-2-3 with Expedia. Step 1: Enter your travel dates and click on the "Search" button. Next, check the "No change fee" box just under the "Flexible change policies" subheading to the left of the screen. Step 3. Score your cheap and flexible ticket to Jessamine County.
Which airlines fly to Jessamine County?
With a great range of airlines flying into or near Jessamine County, you're not short on choice:

  • American Airlines - 368 flights to or near Jessamine County each month, including 368 flights to Blue Grass Airport (LEX) per month.
  • Delta Air Lines - 238 flights to or near Jessamine County each month, including 238 flights to Blue Grass Airport (LEX) per month.
  • United Airlines - 91 flights to or near Jessamine County each month, including 91 flights to Blue Grass Airport (LEX) per month.

How can I find cheap tickets to Jessamine County?
You'll always pick up an unbeatable deal with Expedia, but our "flexible dates" feature makes it that much easier. Enter your preferred travel date, then click on the flexible dates box above to see prices for nearby days. $249 was the best price for a flight to Jessamine County in the last seven days.
How much is a flight to Jessamine County?
The price of a round-trip journey to Jessamine County in the last seven days fluctuated between $249 and $593. If you were flying one way from New York (EWR), you could have scored a bargain from only $141.
What are the most popular airports to fly into in Jessamine County?
Pack your bags and jet into Blue Grass Airport (LEX), Jessamine County's leading flight hub. Book a fare on one of the 789 flights that land here each month.
When is the cheapest time to fly to Jessamine County?
Consider leaving early on in the week to book the best fare to Jessamine County. Tuesday is commonly the most affordable day to fly, with Monday right behind it. Saturday typically has the highest fares. This is because a lot of people prefer to begin their getaway on a weekend.
How much is a plane ticket to Jessamine County?
In the last seven days, plane fares to Jessamine County ranged from $249 to $593.
What months are the cheapest to book a flight to Jessamine County?
The ideal month to secure a fantastic deal to Jessamine County is February, while the priciest month is December. Try to avoid this month if you're watching your pennies.
How long is a flight to Jessamine County?
Flight durations can vary for various reasons, including where you're arriving from. Here is a list of average flight times for some of the top domestic routes to Jessamine County:

  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Blue Grass Airport (LEX) - 1 hour and 22 minutes
  • Chicago, IL (ORD-OHare Intl.) to Blue Grass Airport (LEX) - 1 hour and 23 minutes
  • Dallas, TX (DFW-Dallas-Fort Worth Intl.) to Blue Grass Airport (LEX) - 2 hours and 11 minutes

What is the best time to go to Jessamine County?
Summer starts June 20 in the Northern Hemisphere, and these warmer months are an excellent time to tour the top Jessamine County city of Wilmore. Average temperatures fluctuate between 65ºF and 85ºF throughout this season. The biggest crowds can be found here in June, July and September.

Book with confidence

Enjoy extra legroom, flight flexibility, and a seamless travel experience.

Travel information

*Flight schedules are subject to change.

*Available to One Key members.

 

*Flight schedules are subject to change.

*Available to One Key members.