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Architectural and Historic Bar Walking Tours

Architectural walking tours are a great way to explore Chicago. Our fun, educational tours will give you new perspectives of Chicago architecture and history. Led by expert tour guides, our walking and bus tours include an interactive dynamic, presentation of historic photos and videos, and special gifts.
Tour reservations are required.

Current Tours | Summer 2013

Good Times Historic Bar Tour

Thu 5:30pm, Fri 5:30pm & Sat 5:00pm

On this mostly indoor pub crawl with an educational twist, you’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs. Guests interact with historic photos and videos on shared iPads and visit historic buildings for three drink stops. We don’t walk far and we get to see magnificent lobbies and interesting bars, meaning that we stay mostly indoors. It’s a great wintertime activity.
Appetizers and other extras included - drinks on you.
Book early as this walking tour of historic Chicago bars often sells out.

Tickets: $34 regular, $32 student/senior
Guests pay cash at start of tour to cover all server gratuities and chosen beverage option: $18 for wine, $16 for beer, $5 for soda, $3 for water.

Chicago Underground Group Tours Architecture History

Begin inside Argo Tea, 435 N. Michigan Ave.
End near the intersections of Rush & Ohio streets.
Walk .75 mile - 2 hours & 30 minutes.

Reserve Tour

Inside the Loop Interior Architectural Tour

Mon 11am, Wed 10am, Thu 10am, Fri 3pm, Sat 10am & 1:30pm, Sun 1:30pm

Popular with Chicago locals and visitors wanting an in-depth look at architecture, this walking tour explores architectural interiors and the underground Pedway system. You’ll visit a department store, a skyscraper church, the infamous Block 37, and the Chicago Cultural Center. Guests engage with photos and video clips on shared iPads while a live tour guide shares expert commentary. Part architectural tour, part history tour, and part Pedway tour, you’ll stay warm making this a great winter activity in Chicago.

Tickets: $26 regular, $24 student/senior, $18 age 5-12, Under 5 Free

Chicago Underground Group Tours Architecture History

Meet inside southeast entrance of Chase Tower,
10 S. Dearborn. End at Cultural Center,
78 E. Washington. - Walk .5 mi - 2 hours

Reserve Tour

Jazz, Blues & Beyond Tour by Bus

Saturday, August 31, 10:30am-1:00pm

To design this unique tour, we consulted with music journalists and experts and dug through archives to tell a story of the cultural history of Chicago music. You’ll explore Chicago neighborhoods North to South and enjoy a live blues performance on the bus. Video screens on the coach share historic photos and film clips, and a lively tour guide elucidates how the Windy City became such a hotbed for jazz and blues. We get off the bus for brief walks to engage with architectural landmarks, like Aragon Ballroom, Green Mill Jazz Club, and Chess Records. You’ll get exclusive entrance to a former historic jazz club, and leave knowing how to play blues harmonica.

Chicago Underground Group Tours Architecture History

Starts and ends in front of
Jazz Record Mart, 27 E. Illinois St.
2.5 hours - some walking

Reserve Tour
Chicago Walking Tours Private Groups Pedway
Historical Architectural Detail Tours