Artist · Writer · Illustrator · Educator · Chicago
Architecture,
memory, and the
bright machinery
of a city.
Anna Rae Gilbert makes vivid work about the places that hold us, the stories we carry, and the life happening just beyond a window.
Chicago in motion · Watercolor
Blue Line
“A dwelling is never only a structure. It is a living organism, full of private narratives, public histories, and rooms we keep returning to.”
Anna Rae GilbertSelected work
Portraits of place.
Original drawings become colorful archival prints: part city portrait, part souvenir, part invitation to look again.
Collection 01
Chicago in motion
The L cuts through neighborhoods, over rooftops, and into the skyline, with six lines observed in watercolor.
Collection 02
Chicago architecture
Towers, tracks, ballparks, and glass houses painted as living characters. Each carries a public history and a private atmosphere.
Collection 03
Studio work
Night streets, factories, figures, and unexpected landmarks. A wider view of Anna’s work across watercolor, charcoal, and oil.
Featured print
Chicago Water Tower
A hand-drawn celebration of resilience and architectural beauty, finished digitally and printed at 8.5 × 11 inches with archival inks on matte archival paper.
See the printWriting & public work
Raising resilient
Jewish children.
A growing body of writing for families who want to meet a difficult world with honesty, belonging, courage, and joy.
Digital project · Jewish time and community
נר תמיד
A light for Jewish life, every day.
Ner Tamid is an evolving digital companion for Jewish time, learning, community, and safety. It brings the Hebrew date, candle-lighting times, the weekly Torah portion, prayers, holidays, and practical resources into one calm place.
The central light brightens as Shabbat draws closer, making the rhythms of the Jewish week visible as well as useful.
Visit the live app↗About the artist
Sentiment without apology. Color without hesitation.
Anna Rae Gilbert is a Chicagoland-based interdisciplinary artist, educator, writer, and the founder of Anna Rae Art. Her work explores architecture, memory, nostalgia, and the quietly charged narratives that collect inside the places we inhabit.
She studied at the School of the Art Institute of Chicago, earned her undergraduate degree from Herron School of Art and Design, and received her MFA from Maine College of Art. Her practice moves between fine art, public writing, teaching, and small business.
Selected commissions
Places and people, made personal.
Architectural and figurative portraits made from the stories, photographs, and places clients bring to the studio.
Made for you
Commission a place or a person you want to keep close.
Original 8 × 10 watercolor commissions start at $150, and high-resolution digital illustrations start at $75. Tell Anna about the subject, the story, and the feeling you want the finished work to hold.