Chicago Traveler Blog

Chicago Traveler Blog

Two Warm Winter Ways to Wander Chicago with Chicago Detours

1/8/18 | by

By Amanda Scotese, founder of Chicago Detours.

Architectural walking tours of interiors are a great way to explore Chicago in the winter, especially when epic snows and a polar vortex blast the Midwest. Chicago Detours offers tours that are great for the winter. We explore the Magnificent mile and the Loop on our Historic Chicago Bar Tour and Loop Interior Architecture Tour. On both of our regularly scheduled walking tours, groups stay comfortable inside for most of the tour, and get to see the beauty of Chicago’s magnificent lobbies, corridors, and other indoor spaces like the Pedway system or even a church in a skyscraper.

We like to say that we offer guided tours of architecture, history and culture that bring people to explore stories and places locals don't even know. Founded by former Rick Steves tour guide Amanda Scotese, Chicago Detours designs tours as fun, educational experiences and is a top-rated tour company of Chicago. Led by expert tour guides, our regularly scheduled walking tours include an interactive dynamic, presentation of historic photos and videos on shared iPads, and special gifts. All tours require reservations through

Historic Chicago Bar Tour:

Our “Historic Chicago Bar Tour” is a pub crawl tour is of course not an excuse to drink – that just wouldn’t be our style. Instead this walking tour creates an educational dynamic, as we actively engage with some stunning works of architecture and hear forgotten stories of the many ways that Chicagoans have had fun in the city over time. Guests share iPads with historic photos and video clips while the tour guide shares the commentary. We drink and eat while learning about both iconic and overlooked places just off the Mag Mile. Despite that we tour around this very flashy and fancy area of Chicago, we uncover some pretty unexpected places and stories.

The tour visits the present and former spots of grand balls, Jazz Age shows, elite soirees, speakeasies, theater performances, and more, as our highly trained guides share stories of both scandalous and wholesome forms of entertainment. Tour stops include the original Billy Goat Tavern, 437 Rush which was a former speakeasy and jazz club, and the magnificent Intercontinental Hotel, which is inside an opulent 1920s skyscraper. We also look at some other really interesting buildings in the neighborhood.

It’s part architecture tour, part history tour, part having drinks with new friends, and we offer it Thursdays, Fridays, and Saturdays. It makes for a great date night, too!

Loop Interior Architecture Tour:

Popular with Chicago locals and visitors wanting an in-depth look at architecture, our “Loop Interior Architecture Tour” is a walking tour that explores architectural interiors and visits historic, modern, and contemporary lobbies, passages, and Chicago’s underground Pedway system. Like the Bar Tour, guests get to engage with photos and video clips on shared iPads while the tour guide shares expert commentary. A Detours guest named Grant D. said of the tour, “The interiors tour is a great crash course in Chicago history, especially for visual learners. You really get the feel of the city, all while seeing how it changed over time. And you learn a ton about some of the coolest buildings in the Loop.”

Groups visit the historic Marshall Field’s department store, a skyscraper church, the infamous Block 37, and the Chicago Cultural Center, formerly the Chicago Public Library, with its sparkling mosaics. In addition, we see and discuss some other really interesting buildings, architecture, and public art right in the heart of downtown.

Part architectural tour, part history tour, and part Pedway tour, you’ll stay warm making this a great winter activity in Chicago. We offer it six days a week to work with your schedule, and reservations can be made from our website (