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Chicago Skyline

Hi My Name is Windy: My Chicago Whirlwind

By November 20, 2012 Travel
Goodbye Chicago


Eventually, I think Chicago will be the most beautiful great city left in the world.

~ Frank Lloyd Wright

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I’ve heard a lot about Chicago; some great, some not so great. It’s the home of the Blues, the Cubs, Kanye West, high crime rates, R.Kelly and Obama! When I found out I would be visiting the City of Wind for a work conference, I had lots of interest in getting to know the it firsthand. Was it really as cold as people say? Would I run into Lupe Fiasco? What was all the fuss about that silver bean?

I got into Chicago late Wednesday evening, checked into The James Hotel, which is a very nice hotel in the Magnificent Mile neighborhood and near the Razorfish Chicago office. I grabbed late-night sushi and sake with coworkers and got ready for the next day’s activities.

~ Obligatory Mirror Pic ~ 

Before the sightseeing adventures could begin work had to be attended to. The reason for the visit was a Social Media Summit to discuss the latest and greatest in the practice.

Razorfish Chicago is a pretty outstanding office, my favorite one so far (sorry New York & Philly). Neon walls, bright lights, lots of glass conference rooms. And did I mention… beer on tap. I’m not the biggest beer drinker but you have to admit that’s pretty awesome.

~ Whoop, there it is!  ~ 

Over the next two days there was a ton of exchange, idea sharing and thought leadership. Did I mention I love my job? Well I do. After long days in meetings, it was time for a little Chicago style food sharing. Deep dish pizza, anyone? I now fully understand why Chicagoans are wild about their pie!

~ Delizioso! ~ 

After more meetings, Friday finally winded down and the weekend was set to start. We transferred hotels to the sex-ay W Hotel Lakeshore!  How sparkly is this sign? Very posh!

We headed out on the town and hit up Wicker Park area for scrumptious tacos at Big Star and evening cocktails at Violet Hour, which is a clandestine undercover spot that doesn’t allow cell phone use and has hilarious house rules like: “No O-Bombs. No Jager-Bombs. No bombs of any kind.” and “Please do not bring anyone to The Violet Hour that you wouldn’t bring to your mother’s house for Sunday dinner.”  I love it!

With three cold Chicago nights under our belts, Saturday was officially dubbed the CHICAGO CRAM!

With one full day to sightsee, we decided to see as much of Chicago as we possibly could. I think we accomplished that and more. There must be some sort of award for the most frenzied, yet controlled tourism ever! We’d certainly win.

Dressing for city walking and cold temps is no easy feat. I think I managed well with dark skinnies, black & white striped shirt, leopard blazer (unpictured), bright green scarf, my Shelli Segal coat and comfortable suede boots.

First stop was brunch at the absolutely delectable Yolk, a top rated brunch in the city. It was jumping good!

~ Jaimie loves Yolk! ~ 

Next stop, the TOP of the WORLD! Well the top of Chicago at least! We hit up the John Hancock building and got a view of Chicago from the 96th floor. Insider tip, hit up the ladies’ restroom in lieu of going to the observatory. Backdoor tricks FTW! (Thanks Deanna) 

It was so surreal to see all of the immaculate buildings from so high up. Chicago truly has beautiful architecture and many throwbacks to a classier, jazzier age.

We came down from our high and decided to take an old school horse & carriage ride to get a quicker view of the Chi. Chicago has lots of luxury shopping, traditional hotels, cathedrals and amazing signage. Every storefront has its own unique flair. There was even a cow on the front of a building!

~ Say Cheese ~ 

Next we shot across town to Millennium Park. I didn’t know what to expect of the giant Cloud Gate sculpture except that it seemed pretty cool. Cool is an understatement! Millennium Park is beautiful, has so many different sections, great sculptures and lots of energy. There were about 3 different wedding parties taking pictures!

You’d think we’d be exhausted at this point but we kept the party going and headed to do an Architecture Boat Tour on Lake Michigan. As we rushed through throngs of people (the annual Lighting Parade coincided with our trip – what fate!) we prayed we wouldn’t miss our boat.

And guess what…. WE DID!  Bye Bye Boat.

All was not lost. With the lighting parade came a fireworks display and a later boat ride that ended with seeing the fireworks. On. The. Water. SCORE!

For me, the boat tour was the highlight of the trip. Coasting on Lake Michigan, learning all about the buildings, the companies that inhabit them and the history of the city. Chicago is truly lovely at night.

We parked on the lake and watched the fireworks. It was the cherry on the Chicago sundae. Dinner at the famous Ditka’s (the food was superb) for Jaimie’s birthday dinner and eventually the night ended at the legendary Wiener Circle. I couldn’t get good video because I was laughing entirely too much at the crazy characters behind the counter! But this clip from Conan will show you what WC is all about.

I played a hilarious game and won a T-shirt. Wiener Circle is truly hilarious place and a must visit when you’re in Chicago.

Exhausted from a long day, I conked out ready to head home.

Sunday with only a few hours to spare, we trekked to the Navy Pier, the top tourist attraction in Chicago. The Navy Pier has a giant Ferris Wheel and lots of arcade games.

~ We’re Mad for Chicago ~ 

All in all, Chicago is a pretty spectacular city. It’s like a modern day Pleasantville: clean streets, beautiful buildings and lots to do. Seeing the glorious facade of Chicago makes me want to delve deeper into the parts unseen. 

~ It’s safe to say I’m smitten with the Windy City ~

x Until next time, Summertime Chi!

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