Chicago – My Kind of Town

Chicago – My Kind of Town

Chicago Skyline at night.
This is my kind of town, Chicago is my kind of town,
Chicago is my kind of people too, people who smile at you.
– Frank Sinatra

I grew up in the Midwest but didn’t always appreciate it. I took it for granted — the well mannered people, the change of seasons, the corn fields. I’ve lived in Florida for over 10 years and have not yet become accustomed to the perpetually nice weather. So every fall, I yearn for the brisk Midwestern air and the genteel people with firm handshakes and kind smiles.

This year, I waited as long as my tapping toes would stand, and when I couldn’t wait any longer, I grabbed my husband David, packed our bags and flew to the Windy City. It’s also a plus that my younger brother Brandon and his chic girlfriend Kailee live there. These two are twenty-five year old go getters who know all the hip places to go.

David and I stayed at the Ritz Carlton right off of Michigan Avenue, which is a wonderful central location to walk from. Walking a city is one of my favorite pastimes. It’s usually during those explorations that you stumble on the best things.

Between my own discoveries and the cool places that Brandon and Kailee took us, I came up with this list of the “must do’s” of Chicago.


If you want to be with all the tourists, shop on Michigan Avenue. If you want to feel like a local, venture to the Gold Coast neighborhood for upscale stores and boutiques like Barney’s New York, Ted Baker and Prada. If I lived in Chicago, this is where I’d live. The added benefit of Lululemon on the corner would enable me to never leave my ‘hood.

To feel like a local, you could also take the EL to Wicker Park and sip French press coffee with the young hipsters. Wicker Park is filled with unique boutiques and vintage shops. I’ve been told that if you need any mustache shaping cream, this is where you’d find it. Hipsters apparently can’t get enough of it.

Eating and drinking…

…are two of my favorite things to do in Chicago. The cool restaurants are endless. Here are a few of our favorites:

  • RL Ralph Lauren on Michigan Avenue. Do you want to feel like you are living in a Ralph Lauren ad? Eat here. The dark ambiance sparkles with gold sconces, a crackling fire and traditional paintings. Brunch is a great time to enjoy this crowd pleaser. Just make sure call ahead for a reservation and look your best. You aren’t the only one people watching.
  • The Pump Room at the Public Hotel. Oh, Ian Schrager. You are my favorite hotelier. What a legacy this guy is creating. One of the founders of Studio 54, everything he touches becomes magically hip and chic. The Pump Room was a popular supper club in the 1930s and 1940s and was part of the Gold Coast’s famed Ambassador East Hotel. Schrager recently bought the old hotel and renovated it into another jaw dropping experience. From the entirely white lobby to the globe like light fixtures in the restaurant, you will be talking about it for days.

{The Pump Room}

{David and I at at the Pump Room}

  • Nellcotte is a lovely place filled with candles and beautiful chandeliers hanging from the exposed ceiling. It’s small plates, which makes it a healthy girl’s delight to have only three bites of the best mashed potatoes this side of Lake Michigan. It’s a bit loud, so be sure to sit close to someone interesting.
  • Hot Chocolate is a fun brunch spot. Brandon and Kailee took us here one chilly Saturday. We bellied up to the bar for French press coffee (we were in Wicker Park after all) and rich hot chocolate with homemade marshmallows. I finished it off with a mimosa and quiche, which can fix just about anything.
  • Sprinkles has, in my cupcake expert opinion, thee best cupcakes on the planet. Holy moly. Lots of flavors to choose from, but vanilla vanilla is my hands down favorite. When the vanilla is pure, that’s how you know it’s a really good cupcake. Sprinkles was founded by Candace Nelson, a judge on The Cupcake Wars. Her beautifully creative vision comes through in every detail. If you don’t feel like waiting in line, use the cupcake ATM. It’s all the rage from Chicago to LA.
  • The Bar at the Penninsula Hotel. This is a cozy warm place to rest your tired shopping feet. Set your bags down, kick up your feet and snuggle up by the fire for a mid-afternoon toddy. (Are you beginning to see why this online magazine is called Karousing?) David and I did just that one Friday afternoon. Great people watching.
  • Gilt Bar. Whatever you do, please do not miss this place. It’s dark. It’s chic. It’s a raucous good time. As you scarf down the Midwestern comfort food you are transported back in time to 1930s France. “Midnight in Paris” anyone? A live band plays the French big-band music of times gone by. It is truly a unique experience.

Before I knew it we were saying our farewells to Brandon, Kailee and my favorite Midwestern city. David and I took the train to the airport and on my way to my seat, I collided with another woman pulling a large suitcase. The collision was undoubtedly my fault, and just as the words, “I’m sorry” came out of my mouth, she smiled and apologized to me.

That’s the thing about Midwesterners. We apologize for everything, even if it’s not our fault. A motto, I think, more people should adopt. And, when you apologize, do it with a smile. Who knows? You might even get mistaken for a Midwesterner. And that my fellow Karousers, is never a bad thing.





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