He returned to Chicago in 1871 before travelling to San Luis Potosí, Munich, Paris, the Netherlands, and Italy; in 1880, he moved to New York City.

He died of a heart attack in 1908; his wife donated all of the works that he had left to the Montgomery Museum of Fine Arts, where many continue to be displayed.

Leaning on his education in Munich, he began by depicting well-lit subjects with dark clothing and surroundings; he later incorporated a wider range of colors in his work and even dabbled with Impressionist techniques.

While in Munich, he befriended fellow painter Frank Duveneck; on multiple occasions, the two portrayed each other, or painted the same subject together.

[2] After returning from a trip to the Netherlands in 1883, Freer became an instructor at the Art Students League of New York, teaching drawing and painting alongside his associates Walter Shirlaw and William Merritt Chase.

With her, Freer had six children: Frederick Church, Arthur Warren, Paul Howard, Otto Emil, Catherine, and a sixth child who died in infancy.

[1] Freer continued to be a frequent participant in art exhibitions across America towards the end of the 1880s, and helped create the Chicago Society of Artists in 1887.

[1] Freer's 1887 portrait Lady in Black, depicting his wife, became his first widely successful work,[5] leading to his selection as an associate of the National Academy of Design.

He continued to exhibit his work across the United States during this time and was a founding member of Chicago's Cosmopolitan Art Club.

Near the end of the twentieth century, Freer continued to exhibit his work extensively and served on multiple art committees and juries.

She moved to Fairhope, Alabama after his death, and donated 87 of his paintings to the Montgomery Museum of Fine Arts, where many continue to be displayed.

His early work was heavily influenced by the style of portraiture taught at the Royal Academy, contrasting the bright faces of his subjects with dark clothing and surroundings.

Although especially known for his portraits of females, Freer portrayed a wide range of subjects over his lifetime, including landscapes, classical scenes, and still lifes, moving repeatedly between the aforementioned styles.