3 Perfect Days In Chicago

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 credit card, it’s time to spend.  With your hands full of new fashions, walk back to the Public Hotel and refresh.

It’s dinner time.  Pelago restaurant takes Italian food to a new level.  Chef Mauro Mafrici opened this eatery which has the feel of a New York City restaurant:  Intimate and designed beautifully.  It’s no wonder. The Michelin Star chef used to cook at several top New York eateries. But make no mistake, his roots are in the Old Country. All Pelago’s pastas and breads are homemade at the restaurant with love.  The food is delicious with a modern twist on traditional Italian fare.  And the staff here are on their A-Game.  I’m sure you’ll agree.  This is a great find!

Day 2:

Wake up and stroll along Lake Shore Drive.  If it’s a nice day, stop by one of Chicago’s beaches like Oak Street Beach.  You can enjoy stunning views of the city, all while taking a dip in the waters of Lake Michigan.

Brush off the sand and hop in a cab for lunch at Blackbird restaurant.  It’s been around since 1997 and has become synonomous with innovative dining in  Chi-Town.  The short rib burger is delicious!!  But so are the salads! You’re in for a real treat. Don’t overeat though. Tonight, you’ve got a big dinner ahead of you!

Take a cab over to Grant Park, sight of President Barack Obama’s victory speech in the 2008 Presidential Race.  The park is also home to one of the world’s most famous fountains.  It’s called the Buckingham Fountain and it has been photographed and viewed many times.  Remember the opening of Married With Children? Yes, that was the fountain.

You can make the long walk back to your hotel or cab it. Tonight, dinner at Alinea, ranked the top restaurant in North America. Get ready for 15+ courses of heavenly delight that will get your taste buds dancing with joy. Don’t worry, some of the courses are one bite, so you won’t get too stuffed (just a little!)  If you can’t score a reservation here (I would call way in advance,)  try Moto restaurant, also a gastronomic experience.  Both are VERY expensive but once-in-a-lifetime creative meals.

Dinner At Moto

Day 3:

Today is all about looking at things from different perspectives.  First, seeing the amazing waterways that flow through the heart of Chicago.  The hour long Architectural boat tour will not only provide stealer views, but also plenty of insight about this bustling city.

Head over to The Art Institute of Chicago, but first, stop for some deep-dish delight.  It would be a sin to come to Chicago and not try a slice of the decadent deep dish that is waiting for you.  Lou Malnati’s consistently ranks as some of the best pizza in the city according to several of my foodie facebook friends!

After you’ve finished, it’s time to see some of the greatest art in the world. The Art Institute is a must-not miss!


Edward Hopper’s "Nighthawks"

Even Ferris Bueller skipped school to spend the day here.  Masterpieces like Grant Wood’s American Gothic , Edward Hopper’s Nighthawks and Picasso’s The Old Guitarist line the walls.  At every turn, there’s something magnificent.

Grant Wood's "American Gothic"

Speaking of magnificent, if there’s time, head over to the Willis Tower, formerly known as the Sears Tower.  1450 feet, 110 stories high.  Your ears will pop as you head up to the sky deck to peer down at all the action below.  At one point, it was the tallest building in the world.  It now ranks 7th.


Dinner tonight is close to home.  There are several fantastic restaurants along Chicago’s Rush Street.  Among the standouts: Tavern on Rush and Gibson’s for Steaks.  As one friend remarked, “It doesn’t get anymore Chicago than Gibsons.”

One last thing. If you have time, head on over to Wrigley Field for a Cubs game.  It’s not just baseball you’re after.  It’s to experience the ultimate party!

Now that you’ve tasted Chicago in every sense, it’s time to get some shut eye and start thinking about your next trip to this fantastic city!


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