Historic Night Out on the Town

0 Posted by - January 13, 2016 - Tours, WendyCity

Pick an era: the roaring 20s, the sophisticated 50s, the swinging 60s – and let’s go!  Perfect for a winter’s evening.

WendyCity offers three unique evening tours that are not so much ‘tours’ as they are small group experiences of the city – with a focus on an era.

We bring together history, style, humor, pleasure, and relaxation while moving through historic streets and settling in at glamorous venues —venues with a past.

Each evening tour begins at 6:00 pm, involves less than a mile of walking, is mostly cozy indoors, and ends at 8:30 pm.  Food and drink are up to you – many choices at each venue.  Limited to 8 guests.

1960s in the Gold Coast: Wednesdays, 6 PM

1950s in the Loop: Thursdays, 6 PM

The Roaring 20s: Art Deco & Decadence:  Saturdays, 6 PM

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sidetour july 24















Stephanie Barto

Stephanie Barto

WendyCity’s Roaring 20s: Art Deco and Decadence begins at the sleek 1928 Chicago Motor Club lobby.  After a feast-for-the-eyes Art Deco architectural walk, we relax at the Palmer House lobby and feel ourselves part of that heady era of jazz, speakeasies, flappers, talkies, Al Capone, Al Jolson, radio, trans-Atlantic flight, and delightful style.  What fun and fascinating Chicago history to dig into!  We must toast the end of Prohibition!

The Palmer House lobby is the glorious highlight of my 1950s in the Loop tour.  Not that the 1927 interior necessarily conjures the 1950s, but with the help of the historic images, video, and music that I share with my guests, we may as well be sophisticated midcentury urbanites sipping a cocktail while watching Frank Sinatra perform in the Empire Room.

Palmer House lobby

Stephanie Barto

Another WendyCity evening tour is a mind-boggling celebration of the 1960s in Chicago, specifically focused on the Gold Coast.  I loved how this experience came together: the route begins at the grand Drake Hotel, from which we take an easy city walk past the site of the original Playboy Club, on to storied Rush Street, deeper into the beautiful Gold Coast, and finish at the Public Hotel and its internationally famous Pump Room.  I found amazing images, video, and music to take us back to the 60s… and man, it’s a swinging, swanky, sexy time!  We enjoy some food and drink while we relax and dig into Chicago’s crazy rich history.


1960s in the Gold Coast: Wednesdays, 6 PM

1950s in the Loop: Thursdays, 6 PM

The Roaring 20s: Art Deco & Decadence:  Saturdays, 6 PM

I would love to share a Chicago evening with you!  Marilyn (at the Pump Room) approves.

MM Pump Room

If you’re a history buff or even if you just like good food and drinks, do yourself a favor and book a tour with Wendy!  My coworker had done a tour with her before and I’m so glad she suggested it.  Wendy changed her schedule around to do a private tour with us of the 1950’s Chicago.  She is a wealth of knowledge with a clear love of the subject matter and I thoroughly enjoyed every minute of it.  The pictures and videos on her iPad were the perfect way to help us travel back in time.  Wendy’s warm, friendly personality drew me right in and I felt like I was having a night out with a good friend.  Everything we ate and drank at the Berghoff and Palmer House Bar restaurants was outstanding, and it was clear that Wendy makes friends wherever she goes.  I hear she gives great restaurant suggestions aside from tour stops, too.  Thanks again, Wendy!  You and the tour were an absolute delight. ~Ann, 1950s Nightlife in the Loop


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