Sights & Stories

Experience Chicago’s architecture, history, and culture through stories and places locals don't even know. All our tours fall under this category!


Chicago Holiday Tour of Drinks, Daleys and Dead Guys

On this limited-run holiday tour, we’ll see some classic Chicago holiday traditions and hear off-the-beaten path stories that you expect from Chicago Detours. We’ll venture into a few cozy locales and talk history over a couple drinks. (Non-drinkers welcome too!)

Loop Interior Architecture Walking Tour with Pedway

On this tour, you’ll step into magnificent interior spaces and the underground Pedway. We’ve planned a creative route that weaves through buildings and secret short-cuts.

Historic Chicago Walking Bar Tour

See a secret side to Michigan Avenue on this historic Chicago pub crawl with an educational twist!

1893 World’s Fair Tour with Bars

The 1893 World's Fair Tour with Bars digs into how and why the World's Columbian Exposition still captures imaginations more than 120 years later.

Free Chicago Walking Tour Inside a Historic Skyscraper

This free walking tour of the Monadnock Building showcases its monumental architecture, gorgeous interiors and groundbreaking restoration. All gratuities for this tour will benefit the non-profit Preservation Chicago!

Best Architecture Walking Tour for Design Lovers

Available April-October. The Architecture Walking Tour for Design Lovers is a creative tour of Chicago architecture. We designed it for curious people.

Factories to Calories Fulton Market Food Tour

Available April-October. Discover the dramatic transformations of Chicago's most rapidly booming neighborhood, get a glimpse of Fulton Market's meatpacking past and enjoy a taste of its gourmand present.

Old Polonia and Wicker Park Tour with Food

Available April-October. On the Wicker Park food tour, you will explore the past and present of the people, architecture, and foods of Noble Square and Wicker Park, two vibrant and rapidly changing communities.