2 Cool Hotel Bars in Chicago and the Tip Top Tap

Chicago is one of my favorite cities and during a recent visit I saw first-hand how vibrant the hotel scene is there. Landmark favorites like The Drake and The Palmer House have survived and even thrived as grand dames, but a number of new hotels sparkle and shine. Take a look over at TravelSkills.com for my roundup of three new and notable Chicago hotels, as well as a heads-up on properties in the pipeline.


Order up a whisky: Bernard’s Bar in the Waldorf Astoria Chicago is intimate and clubby.

Writing the TravelSkills piece found me thinking about how during my most recent visit to Chicago, two hotel bars knocked my socks off. And that never happens. The first was Bernard’s Bar, in the newish Waldorf Astoria on the Gold Coast (11 E. Walton). This was the most gorgeous clubby bar I’ve ever been in—I felt like I was in the library of a new millionaire friend’s home. If I were a man, and if it were legal, and if I did such things, Bernard’s would almost certainly make me want to smoke a cigar! By the way, I was crazy about the hotel overall and highly recommend it.

The view from the Terrace at Trump is breathtaking. (Photo: Trump International)

The view to the lake from The Terrace at the Trump is breathtaking. (Photo: Trump International)

The other standout was The Terrace at the Trump rooftop bar in the Trump Hotel (401 N. Wabash). It is such a special luxury to inbibe outdoors on the 16th floor—a very rare experience in downtown Chicago.  What a view! The large space looks straight down the Chicago River to the lake—a spectacular place for a glass of wine after work.


This sign from the long-closed Tip Top Tap has inspired lounge dreams for decades. (Photo: Flickr/Owen Byrne)

Speaking of a bar with a view, long ago when my friends and I were single, we fantasized about the Tip Top Tap in the Allerton Hotel on Michigan Avenue. We knew the lounge had closed years prior but many nights we’d gaze up at its prominent sign on the skyline (which remains to this day) and wonder what we’d missed. Doesn’t the Tip Top Tap sound like just the right place to end an evening? Apparently, it had been a pretty swanky scene in the ‘50s and ‘60s, and we imagined the view would be to die for. So, good news: The Allerton was purchased earlier this year and rebranded as the Warwick Allerton, and the new owners have not ruled out revival of the Tip Top Tap. One can only hope.

What makes a great hotel bar? Weigh in with a comment. (And if any readers visited the Tip Top Tap in its heyday, I’d love to hear about what it was like.)

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