Walking Tours – Page 2 – Discovering Chicago

Chicago Walking Tour: Historic Treasures of Chicago

/ June 4, 2026

Chicago clicks on this walk. This small-group Loop tour mixes quick sights and expert narration as you move between Michigan […]

/ June 4, 2026

Ghosts and gangsters walk the South Loop. What makes this tour fun is how it uses real city landmarks to

/ June 4, 2026

Chicago never feels smaller than on this walk. You get a tight mix of icons—food, skyscrapers, the river—plus the stories

/ June 4, 2026

Chicago hides architectural trophies in plain sight. This 2-hour walking tour pulls you into the Loop’s grand buildings and select,

/ June 4, 2026

Gangsters and lunch in the same walk sounds wrong. It works. You’ll pair River North Prohibition-era storytelling with three Chicago

/ June 4, 2026

Chicago hides its best details in plain sight. This walking tour through the Chicago Loop focuses on what you usually

/ June 4, 2026

Ghosts and gangsters hit the Loop at night. This Chicago tour turns the Roaring Twenties into a street-level story you

/ June 4, 2026

Chicago hides its best routes underground. This 2-hour tour takes you through the Pedway—downtown tunnels that keep you warm and

/ June 4, 2026

Chicago’s ghosts love a good drink. This walking pub tour pairs period-dressed guides with real stories from Lincoln Park and

/ June 4, 2026

Chicago tastes better when you walk it. This 3-hour downtown food-and-sights outing strings together famous landmarks like Millennium Park and

/ June 4, 2026

One bad corner can tell a whole city story. This walking tour trades the usual postcards for mob hangouts, haunted

/ June 4, 2026

Chinese food in Chicago has a story. This small-group Chinatown food and walking tour strings together regional bites with neighborhood