Cindy’s on Michigan was our destination as we set out on our 5 1/2 mile walk from Lakeview.  It was a beautiful sunny October morning, perfect for a stroll along the lake.  Choosing to go inland along the Miracle Mile for our last leg, we stuttered after crossing Madison before finally identifying the entry to the 13 story Chicago Athletic Association’s 1893 Venetian Gothic hotel (1), upon whose roof Cindy’s (2) sat.  There was no marking other than the 12 S. street address.

You had to go through the lobby to the elevator before seeing a small sign to Cindy’s.  If you looked down off Michigan, out could see the worn logo of the CAA on the rug in front of the door. 

For the first 123 years of its existence this home of the Chicago Athletic Club was a private club, a hotbed of social activities and athletics.  A few mementoes of that past are on quiet display

On the way up the elevator to Cindy’s you’re reminded that this place is still home to some sweating with a purpose.

Once up and in, it was clear from the Monday brunch crowd that the place was no longer a very well-kept secret, even if you had to work to find it.  It’s hard to get a seat there, but there’ll be no sitting whatsoever on their deck.  Patrons may bring their libation out there to admire the view – and in summer be served by a bar right on the deck – but sitting and eating must take place inside.  The deck commands the best outdoor views in all of Chicago (the observation decks of those skyscrapers are all enclosed), with the lake and the park straight ahead, flanked by architecture to the left and museum row to the south.

Looking east from Cindy’s deck you see out to Monroe Harbor and Lake Michigan.  Millennium Park is in the Foreground, with the skating rink to the side and the seating area of the Jay Pritzker Pavilion crisscrossed by metal bands.  Beyond to the lake is Maggie J. Daley Park (she was Da’Mere’s beloved wife).  The skyscrapers you can see on East Randolph include the deep blue Blue Cross Blue Shield building and the rounded black shiny building at the end, the Park Shore Condominiums, where my brother-in-law Bob lived for a year.  Cut out of the picture to the left of BCBS is “Big Stan” (once the Standard Oil building, now the AON building), the 3rd tallest skyscraper in Chicago.

Looking southward you see mainly the buildings of the Art Institute.

The little round bump on the end of that spit, the Adler Planetarium, makes the east end of the Museum Campus. Just in from there at the foot of the spit is Shedd Aquarium and in from there the much larger Natural History Museum.  Way, way beyond that on the water are the buildings of the South Shore neighborhood.

Even when you’re done taking the view, the bar/restaurant is pretty good, with fancy cocktails and fine food served under soaring ceilings.

As you come back down the elevator and step onto Michigan Avenue, the fun is hardly over.  You can turn right and ascend the stairs between the lions of the Art Institute to go in and see your Monet, van Gogh, Seurat, Picasso, and such, or you can turn left into Millennium Park, climb the steps to Cloud Gate (“The Bean”) and see yourself in all sorts of distorted ways.  Once done, you can walk back to Michigan and look up to see where you’ve been.

You can make reservations at Cindy’s through RESY, with a booking window of one month.


  1. Chicago Athletic Association.

2. Cindy’s.

Published by rike52

I retired from the Rheumatology division of Michigan Medicine end of June '19 after 36 years there. Upon hitting Ann Arbor for the second time (I went to school here) it took me almost 8 months to meet Kathy, 17 months to buy her a house (on Harbal, where we still live), and 37 months to marry her. Kids never came, but we've been blessed with a crowd of colleagues, friends, neighbors and family that continues to grow. Lots of them are going to show up in this log eventually. Stay tuned.

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