Chicago: Only Have Two Recommendations, Both Outstanding


My #1 Recommendation for Chicago is Soho House (and #2 is the new Amazon Go)

  • Absolutely LOVE Chicago’s Soho House. It was my salvation on both ends of my trip.
  • Even if you are not a member, you can come here to dine at The Allis Restaurant or stay at the hotel which is open to the public.
  • It’s where I ultimately recuperated at the beginning of my stay and it’s where I spent 12 hours on the last day while awaiting my sleeper train back to NYC.
  • It’s my favorite House of all those I’ve visited. It’s big, it’s gorgeous, the staff is wonderful and the members seem to be super nice.
  • They also have a huge work area where phone calls are allowed which is incredibly helpful – other houses should look into this!
  • I could kick myself for not staying here. Room rates for members are almost identical to the horrid Freehand where I was staying. I even tried to switch hotels but of course they were booked solid by the time I got to Chicago.
  • No photos allowed but I found the above interior shots online.

Other than Soho House and Amazon Go (see below), I would say Chicago was a bit of a bust for me.

  • I arrived feeling sick. The weather was cold and blustery. My hotel was awful.
  • In the interest of full disclosure, I have never been an aficionado of Chicago so even without all the problems associated with this trip, I might find it hard to whip up a lot of enthusiasm for the city.


Read on below for what I did manage to check out while in the Windy City – and most especially for my experience with Amazon Go – totally knock-your-socks-off.  Wow!


AMAZON GO (113 S. Franklin Street) Open 7am-8pm Mon-Fri

We have yet to get one in NYC so was excited to check them out in Chicago. IMPRESSIVE: well-informed staff, great layout, exceptionally well-curated merchandise (the latter is rarely mentioned but I believe it’s crucial to what makes Amazon Go such a hot destination).


Amazon plans to open 3,000 of these cashierless convenience stores by 2021.

And based on an analysis of the first Amazon Go store which opened in Seattle in January sales are through the roof:

  • That initial store in Seattle generates $2,700 in annual sales per square foot, a figure surpassed only by Apple ($5,600 in annual sales per square foot). When you consider Apple is selling $1,000 iPhones, while Amazon is selling food items for under $10 each — Amazon Go is all the more remarkable.

Here’s how it works:

  • You download the Amazon Go app to your smartphone and prep it prior to use. There’s quite a bit of swiping and so on involved before you can set foot in a store.
  • The app gets activated when you swipe it as you enter the store.
  • It then becomes aware of your movements throughout the space, knowing what you pick up and put down.
  • There’s no need to interact with a human; you pocket whatever item you want, and through an array of cameras, sensors, artificial intelligence, and machine learning, the Amazon Go store knows what you’ve selected and charges your Amazon account accordingly.
  • It’s clearly a convenience store rather than a supermarket. Most are not open on the weekends and also close at around 8pm.
  • The selection of merchandise is impressive. A great mix of brands including Amazon Go Exclusives. The overall perception is much more premium than anything you’d find at a typical convenience store.
  • The food options skew to salads, sandwiches, meal kits and LOTS of chocolates, desserts and snack foods.
  • Notable brands included: Pellegrino, Farmer’s Fridge, Burt’s Bees, Mrs. Meyer’s, Vosges, Lindor.
  • Everyone who’s got a hot brand is going to want to get it into Amazon Go. Reminds me of how the Cosmopolitan Hotel in Los Vegas is a magnet for hot brands and always gets them first e.g. Egg Slut, Dry Bar etc.
  • Analysts estimate that the Seattle store is generating about 50 inventory turns per year, or some four to five times the number of turns a typical retail operation can produce. There were quite a few out of stocks at the store I visited (OOS signs humorously tell you it’s “so good, it’s gone.”)



NEW MCDONALD’S (600 N. Clark St)

This is considered the “Apple Store of Fast Food.” Looks great, very techie but also “green.” However, once inside, it’s still filled with the same homeless people you’ll find elsewhere.



NEW APPLE STORE (401 N. Michigan Avenue)


It’s cool enough. And I do love the way it’s tucked in down by the river. But I am so over Apple stores – I mean when the McDonald’s becomes the Apple Store of fast food, there’s got to be a new style we can get excited about.





On a warm day this is undoubtedly great. On a frigid and blustery day – don’t bother.

  • I DID bother, however, and hung around above deck as long as I could bear it but had to go below OR get even sicker.
  • Listening to – and trying to see – what our architecture guide was pointing out, is impossible from below deck. First, everyone around you is chitchatting and second, every direction is opposite of where you are being directed to look.
  • Also, this river tour (vs. the one in NYC) reverses itself on the river several times as opposed to making one grand loop around Chicago.
  • 3 star (out of 5).




I’ve been a huge fan of the Sydell’s Group’s Freehand brand. I’ve been to the properties in Miami, LA, and NYC. How the Chicago one could turn out as badly as it did is a mystery to me.

Do NOT stay here even if you’ve heard me rave about all the other locations.



Being sick put a serious crimp in my restaurant explorations. I only checked out one place – Pacific Standard Time. The restaurant looks great but the one item I ordered (the cod) was OK, not great. So got nothing for you on the food scene for Chicago!



Bottom Line.

I know many of you love Chicago. It’s just not my scene. I have some great friends there but the city doesn’t rock my boat.

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