Cheap flights from Chicago to Lake Cumberland

View AU$342 flight on Sun, 31 Aug. 2025Opens in a new window

Popular airlines from Chicago to Lake Cumberland

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago (CHI) to Lake Cumberland (LEX)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
LEX
Lexington
AU$336 Return, found 6 days ago
AU$336
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$336 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
LEX
Lexington
AU$356 Return, found 6 days ago
AU$356
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$356 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
LEX
Lexington
AU$385 Return, found 6 days ago
AU$385
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$385 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
LEX
Lexington
AU$397 Return, found 6 days ago
AU$397
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$397 found 6 days ago
American Airlines
Sun, 31 Aug. - Sun, 7 Sep.
ORD
Chicago
LEX
Lexington
AU$404 Return, found 6 days ago
AU$404
Return
found 6 days ago
Select American Airlines flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$404 found 6 days ago
Delta
Sun, 31 Aug. - Sun, 7 Sep.
MDW
Chicago
LEX
Lexington
AU$618 Return, found 6 days ago
AU$618
Return
found 6 days ago
Select Delta flight, departing Sun, 31 Aug. from Chicago to Lexington, returning Sun, 7 Sep., priced at AU$618 found 6 days ago

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

November is typically the cheapest month to fly

From AU$189 - AU$747 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.