Chicago's Roaring '20s or Riverwalk Brunch Tour for Two from Chicago's Finest River Walk Tour (Up to Half Off)

The Loop

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In a Nutshell

The '20s come to life through classic buildings; walk along the scenic Riverwalk for a tour and brunch

The Fine Print

Expires Oct 31st, 2013. Limit 10 per person. Valid only for option purchased. Reservation required; subject to availability. Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services.

A walking tour acquaints you with the city around you, helping you avoid disaster during future scavenger hunts and upcoming bouts of amnesia. Get a few steps closer with this Groupon.

Choose Between Two Options

  • $25 for a Chicago's Roaring '20s tour for two (up to a $50 value)

During the 1920s, notorious figures roamed Chicago—including a bootlegger named Al Capone. Characters like Capone traveled through a city infused with jazz and saw the construction of plenty of iconic buildings. This three-hour walking tour, subtitled Buildings, Booze & Jazz, discusses the historic events of the time and strolls past classic buildings, including Tribune Tower and the Wrigley Building. This tour takes place every other Thursday at 4 p.m.

  • $45 for a Riverwalk brunch tour for two (up to a $90 value)

On Saturdays and alternating Sundays at 10 a.m., the Riverwalk brunch tour wends along the Chicago River. Once home to industries that helped Chicago grow into what it is today, the river now flows past scenic cafés and green spaces that each tell a story of the city's past and present. In the middle of the three-hour tour, groups stop by Houlihan's for a delectable brunch buffet (included in the price of the ticket), during which guides tell more tales of the city's history.

See more about each tour here.

Chicago's Finest Tours

The history buffs of Chicago's Finest Tours lead engaging and dynamic tours of two very different parts of the city. During the summer, intimate groups of up to 15 traverse the various walkways of the bustling yet majestic riverfront or climb aboard a boat for a sunny river voyage, soaking in vistas of Chicago's many architectural wonders. In the winter, tourgoers head below the sidewalks with torch in hand to explore the troll-populated tunnels of the Pedway, Chicago's underground network of shops, hotels, train stations, and eateries. Regardless of the tour, the knowledgeable guides engage strollers in a two-way conversation about the Windy City, enlightening audiences with historical yarns and humorous anecdotes.


We took the Chicago History Tour and we really enjoyed learning about the Pedway system at the same time.

ShicksCreative, TripAdvisor, 2/1/12

What a fabulous discovery of the pedways during our history tour! Highly recommended!

Carcoverlady, TripAdvisor, 2/7/12


94% of 1,120 customers

  • “Very educational tour which is well worth ones time to learn many interesting facts about the city of Chicago”

  • “Great fun, energetic tour guide. ”

  • “Loved it! Our tour guide was fantastic with so many great stories of the "roarin' 20's"! I would definitely recommend this tour and with the groupon it really pays...”

    “Loved it! Our tour guide was fantastic with so many great stories of the "roarin' 20's"! I would definitely recommend this tour and with the groupon it really pays for itself since you get 1 drink and some light apps along the way. Great way to check out a few places in Chicago with history & stories along the way.”

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    The Loop

    111 E Wacker Dr.

    Chicago, Illinois 60601

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