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A city comes alive when you can stand on a corner and glimpse yesterday behind today’s skyline. That’s the spark behind my conversation with Ryan Wilson, a designer and mariner who turned countless hours in archives into the Chicago History Map—a large-format, interactive portal where high-resolution photos meet precise locations and time fades just enough for details to surface.

We talk about the winding path that led from Admiralty charts on private yachts to digitized street scenes, and why visual design can make genealogy, urban history, and public memory feel immediate. Ryan walks us through the choices that keep the experience human: desktop-first for big images, intuitive hover interactions for quick context, and a workflow that mixes Affinity apps, Image Map Pro, and a lean site builder. The result invites you to zoom into specifics—storefront signage, transit lines, architectural facades—and to link names, neighborhoods, and events with evidence you can study.

Attribution and ethics are a throughline. As images drift across social media without credits, Ryan anchors each photo to institutions like the Newberry Library, Library of Congress, and Chicago Public Library, restoring provenance so researchers and curious minds can find companion materials and verify dates.

We also explore the thrill of discovery—hidden collections, estate finds, and the Vivian Maier story—and why independent creators are vital to preserving local history. Chicago’s layered neighborhoods become a living syllabus, and help historical events, connecting historical events like the Eastland Disaster to the streets, jobs, and homes that shaped real lives.

If you enjoy Chicago history, genealogy, cartography, or simply great design that makes knowledge accessible, you’ll love this one. Explore Ryan’s work at VagabondStudiosDesign.com and ChicagoHistoryMap.org (links below).

Resources:

🧭 Ryan Wilson's site: Vagabond Studios

🗺️ Dive into Ryan Wilson's Chicago History Map Project

🖼️ Vivian Maier Photography Archive

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