Earn point on your loyalty program!arrow arc left

Cheap flights from Lexington (LEX) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)

How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.

Cheap flights from Lexington to Chicago in May , June 2026

31 May - 07 Jun $ 334.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates
31 May - 07 Jun $ 334.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates
31 May - 07 Jun $ 334.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates

Last minute flights from Lexington to Chicago

24 May - 31 May $ 347.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates
24 May - 31 May $ 347.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates
22 May - 31 May $ 466.00
LEX
Lexington
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
LEX
Lexington
Pick dates

One-way flights to Chicago from Lexington

9:44 PM - 7:30 AM
Allegiant Air
1 Stops
12h 37m
LEX - CHI
$ 148
Kiwi
Pick dates
5:45 PM - 5:45 PM
United Airlines
0 Stops
1h 46m
LEX - CHI
$ 358
Kiwi
Pick dates
6:03 PM - 6:03 PM
United Airlines
0 Stops
1h 48m
LEX - CHI
$ 358
Kiwi
Pick dates

How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)

Related info for your journey
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Lexington (LEX) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.