Historic Chicago Walking Bar Tour


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76 Have Dabbled
4.5 | 3 reviews
Registration closes at 24 hours before event

Register for this Experience

Join us for a historic Chicago pub crawl with an educational twist! You’ll explore Chicago’s entertainment history and learn about prohibition, jazz, theater, vices, and social clubs, all while enjoying drinks and appetizers.

Guests interact with historic photos and videos on shared iPads and visit historic buildings for three drink stops. We don’t walk far on our evening walking tour, giving us more time to engage with Chicago history and look at architecture. The limited walking distance on the tour gives us time to enjoy our appetizers and choice of wine or beer.

Tour groups see magnificent lobbies and really engage with some beautiful historic architecture. Many tour guests enjoy the social dynamic of this unique tour. Solo travelers often join the tour. Also as a great Chicago date idea, it can be a fun thing to do in Chicago with your boyfriend or girlfriend. Groups of friends make the tour into a cool weekend event as it’s more than a Chicago pub crawl – you’ll eat, drink, and learn about architecture, Prohibition-era history, and culture.

Stories and Ideas on the Historic Chicago Pub Crawl Tour:

Architecture as a cultural artifact
The “Hex of the Billy Goat”
Chicago jazz era
History of Chicago breweries
Prohibition and gangsters
Historic restaurant trends
1960’s nightlife
Private clubs

Materials to bring

Each guest must choose a beverage option ($20 for beer, $22 for wine, $6 for soda, $3 for water). Covers 2 regular size drinks, 1 sample-size drink, and server gratuities on the drinks and the appetizers (apps are included in the tour).

Argo Tea at Tribune Tower
Illinois & Michigan
Chicago, IL, 60611

Student Reviews

4.5 | 3 reviews
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    Miriam G.
    Historic Chicago Walking Bar Tour

    Do it a warmer day because you do spend a lot of time outside. Even if you're a local, you'll learn some interesting things you never knew about Chicago history.

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    Kateland G.
    Historic Chicago Walking Bar Tour

    This was such a fun way to be a tourist in my own city! :) I think whether you are out of town or a lifelong Chicagoan, you could have a great time and learn something from this class! It was fun, interactive, entertaining, and I learned some really cool stories about some Chicago staples (and a couple off the path places). I'm not the typical history buff who wants to learn the details and facts and years, but I do love hearing stories. While Elizabeth did know the facts, she also told them in an engaging way. :) I would definitely recommend checking this out!

  • Default user photo
    Maeve R.
    Historic Chicago Walking Bar Tour

    This was an excellent tour for tourists and locals alike.

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Multiple Guides at Chicago Detours

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We are a group of educators, historians, artists and story-tellers. Founder Amanda Scotese launched Chicago Detours in July 2010 after close to a decade of travel in Italy as a Tour Guide and Guidebook Researcher with Rick Steves’ Europe. She decided to bring her travel expertise back home with tour experiences that are fun, educational, and truly make us feel connected with our grand city. Our professional Chicago tour guides are highly trained and educated, and we know how to spark discussions and create a lively group dynamic on our public and private group tours of Chicago. Today we are a community of Chicagoans passionate about sharing the architecture, history, and culture of Chicago through the Chicago Detours blog and our guided walking and bus tours.