When he was about twenty-one, Dudley moved to Chicago to study at the School of the Art Institute under John H. Vanderpoel and Charles Boutwood. At this time Dudley also had at least an introduction to impressionism by virtue of the 1893 World’s Columbian Exposition, which has since been considered the "watershed for public acceptance" of the new French aesthetic. Dudley married Haley Boxwell several years before their son Paul was born in 1898. He supported his family with the commissions from portrait photographs worked over in crayon and a special watercolor medium. It does not appear that Dudley submitted work to exhibitions of a national scope prior to the turn of the century; however, by 1902 his first painting was accepted for exhibition at the Art Institute of Chicago. Following the sudden death of his wife in 1904, Dudley appears to have concentrated upon landscape painting in the plein-air manner. One year later he became a recipient of the Art Institute’s Young Fortnightly Prize.

In 1911, Frank first visited the Indiana Dunes. Soon he began to record their unmolested scenery (Dudley to Love, 1977). Two years later Frank Virgil Dudley married his second wife, Maida Lewis, with whom he passed the rest of his years. It was not a long trip from the Dunes to Chicago by horse and buggy or via the then-risky automobile. At selected vantage points in their quiet, simple environment, the artist (with his wife seated nearby) stationed his easel to paint all’aperto in a manner that combined broad, sweeping brushstrokes with textural contrasts of broken color. Dudley centered attention upon every pictorial aspect of the lonely area but selectively relegated each to provide a harmonic pictorial balance. Maida described her husband’s artistic sensitivity to that unique slice of sand, grass, pines, and rolling waves: "The Dunes were irresistible, fascinating to him. They were wild and majestic and fresh. He painted them in all seasons and communicated emotion in them to others." (Chicago Tribune, 3 September 1967; quoting Mrs. F.V. Dudley).

Dudley was active in the second decade of the century: in 1915 he won the Art Institute of Chicago’s Butler Prize. The Art Institute also presented a show of his dunes pictures in 1918. Critics were generally complimentary. A year later the Art Institute presented Dudley with the Cahn Prize for his painting The Silent Sentinels. During these years he was unable to devote full time to painting because he ran an art supply store. The funds this provided were needed, but he gave up the business in 1921 to spend all of his time painting in the dunes. Whereas Dudley maintained his residence in the city, by 1921 he had designed and built a log cabin studio in Indiana, so that he could "bring the Dunes indoors." (Dudley to Love, 1977). From this primitive base the artist painted the surrounding area, capturing the quiet evanescence of its multi-faced simplicity. Titles such as Winds in the North or Soft Shadows across the Sands or Under Changing Skies, Dunes, indicate his concern not only with the constantly changing picturesque characteristics of the scene, but also with the extreme effects of the Lake Michigan atmosphere. Although Dudley exhibited little on the national level, he was very active in the Midwest and became known as the "Dunes Painter" or "Painter of the Dunes."

As an avid ecologist and conservationist, Dudley joined others interested in maintaining the natural beauty of the dunes, reminding his contemporaries of their simple pleasures of living there: the graceful flight of a sand-hill crane or the delight of a wild strawberry shortcake. Both his art and the area his brushes depicted were devotions, reflected by Dudley’s lifelong production of painting canvas after canvas showing the Indiana Dunes. In fact, when the Dunes were declared an Indiana state land reserve in 1923, Dudley was successful in persuading officials to allow his cottage to remain there; he did so by trading his right to work in his dunes studio for one of his pictures per year. Frank Virgil Dudley died in Chicago on 5 March 1957, eight months before his ninetieth birthday. Recently (1997) the Brauer Museum in Valparaiso, Indiana organized a retrospective of Dudley’s Dunes paintings. The museum has the painter’s stunning Shadow and Sunlit Silence, which features dramatic purple shadows in the middleground.