Despite what Wikipedia claims, Liberty was seldom (never?) a serious rival to the Saturday Evening Post in the realm of American general-interest magazines. That is indirectly indicated by the fact that Liberty's cover artists, while entirely competent, were seldom in the absolute front rank of their day. Below are some Liberty covers in chronological order.
Ruth Eastman - 7 February 1925
Walter Beach Humphrey - 14 March 1925
The title of this cover is "Back from Palm Beach" (tee hee, that's a pun, folks).
Leslie Thrasher - 2 March 1929
Havana was a popular place to visit in winter for affluent Americans. Cuba Libre is also an alcoholic drink.
I didn't find any useful biographical information on Warren, who was active in the 1930s. This illustration is surprisingly era-free; it almost could have been painted yesterday. That might have been because 1932 was during a transition from short to longer hair styles for women. Another factor is that the clothing is hardly shown, so can't be pinned to a fashion era.
There was a Lumen Winter who was best known (according to Wikipedia) as a muralist. His signature was different than that on this cover. But it's likely that we're dealing with the same Lumen Winter.
Snazzy Hallowe'en witch we have here. I wonder who the illustrator was.
Walter Baumhofer - 4 April 1936
Here Baumhofer was beginning his transition from "pulp" to "slick" magazines.
Zippy car, attractive gal. Unfortunately, I have no information about Scott Evans, a common name.
Herbert Paus - 15 April 1944
I suppose Paus set this scene in a war-damaged Italian church, because Italy was where American troops were in action a few months before the D-Day invasion of France.