To quote the late, great Frank Sinatra, “This is my kind of town, Chicago is!”   I couldn’t agree more.  And if you’re going to tackle this Mid-Western gem, you might want to begin this way:

Day 1:

Start by checking in at the Public Hotel, in Chicago’s affluent Gold Coast neighborhood.  The property is newly renovated and rich with history. It used to be The Ambassador East, a place where Frank Sinatra, Ronald Reagan and Judy Garland used to socialize.  It was recently acquired by famed hotelier and former Studio 54 guru Ian Schrager, who took this place well into the millennium with sophistication, grace and that hip vibe you need to bring in all the cool folk.  Modern and classy, it is the IT hotel in Chicago. At night, the hotel’s restaurant/bar, The Pump Room, is packed and the music is kicking.

The Pump Room At Public Hotel, Chicago

Public Hotel: Lobby

Put on your walking shoes. You’re going to need them.  Exit the hotel and walk toward Chicago’s most exclusive street, Michigan Avenue.  Make sure you’ve got your wallet handy. Today, isn’t about “window” shopping. It’s about shopping! Chicago’s Michigan Avenue and the area around it known as the “Magnificent Mile” is a shopper’s paradise.  You’ll be surrounded by skyscrapers as you make your way south. Hold on a second. You aren’t going to do your spending just yet. First, you want to head to Millennium Park.  This is a great place to stroll around on a sunny day.  You’re here to look for a big, shiny, grey object that looks like a giant piece of mercury.  It’s called Cloud Gate, a modern art piece.  Try and spot yourself in the shape.  Fun, interesting, and just plain cool. It is one of Chicago’s treasures and most talked about things.

Cloud Gate

Cross the street and head back up Michigan Avenue, stopping along the way at your favorite shops.  Get out your [Read more...]