1960s Nightlife in the Gold Coast

0 Posted by - September 28, 2015 - Tours, WendyCity

An evening featuring the Drake Hotel, Rush Street, and the Pump Room.

Fridays at 6:00 pm. BOOK NOW

WendyCity tours are all about going back in time to experience the Chicago of an earlier era.  And one of the most exciting eras to explore is the mid-twentieth century.  My 1960s Nightlife tour is not so much a tour as it is an immersive experience.  I share video, music, and evocative vintage images that bring the past to life.

Vivian Maier 1963

Vivian Maier 1963

We begin at the elegant Drake Hotel and explore what nightlife was all about in the swinging 60s: everything from swanky to sexy.  We will focus on the Playboy Club and Hugh Hefner, fixtures of the area for decades.  Then it’s on to Rush Street with its storied past of the classiest entertainment rubbing elbows with the darkest vices.  We further meander through the Gold Coast, enjoying one of Chicago’s most beautiful and historic neighborhoods, complete with mansions and gaslights.  Finally, we enter the famous Pump Room, destination for scores of celebrities over the decades; we’ll even see Frank Sinatra’s private booth.

MM Pump Room


“Once again had a wonderful time. I loved the pictures making it much easier to really visualize the past. I also love being able to stop in venues along the way to get a chance to taste and drink the best the city has to offer. Wendy’s groups always have interesting guests too.” ~Bernadette, 1950s Nightlife in the Loop

Meeting Point:  The Drake Hotel, Michigan Avenue and Oak Street, at the Oak Street entrance 

Tour End: Pump Room at Public Chicago, 1301 North State Parkway

Running Time: 2.5 hours, walking less than one mile.  

Drinks and appetizers at the Pump Room are up to you – many options.

“Very fun and interesting tour. Great way to learn more about Chicago’s fascinating past.” ~Cathy, 1960s Nightlife in the Gold Coast

Subject matter on this tour recommended for adults only.

Price: $50 / $100 tour minimum


Please call *text * email me with any questions: 312-810-6609 or wendysue302@yahoo.com

“I have lived in Chicago my entire life … and I learned so many new things and saw amazing, beautiful places I never knew existed! When you live somewhere you don’t always take advantage of all it has to offer and you go about your daily activities missing all the beauty around you. Wendy is so knowledgeable and passionate and showed me all there is I am missing.”  ~Sarah, 1950s Nightlife in the Loop





  • WendyCity Tours This Week | WendyCity October 8, 2015 - 5:03 am Reply

    […] 1960s Nightlife in the Gold Coast […]

  • Leentje July 23, 2016 - 8:26 am Reply

    Being an off the beaten path tour guide myself I am always up for something new or different. This tour definitely ticked all of my boxes: it was different, fun, not too long, small sized group of very nice people, and of course: there were drinks involved. Thank you Wendy for a great Friday night!

    • Wendy July 24, 2016 - 6:10 pm Reply

      That means so much coming from you, Leentje!

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