By Ashley Goldsmith


I don’t vacation too frequently, but when I do, it always happens to be in another major city. Which often raises the question: If you live in one of the greatest cities in the world, like our beloved New York, does it still feel like an escape when heading to another? I decided that this trip would be an exploration in urban tourism, so a girlfriend and I headed to Chicago, the Second City, for our experiment.

First things first – our hotel was almost our favorite thing about the vacation. I know what you’re thinking, a vacation where you spend a lot of time in your hotel room is never good, but our bed was the most comfortable mattress that I’ve slept on, well…ever. (So comfortable in fact that we tried to lift the bed up before leaving to find out what type of mattress it was!)

Rooms at Hotel Felix

Said hotel is the Hotel Felix, located at the crossroads of the Gold Coast and River North and just blocks from shopping-central on North Michigan Avenue. This boutique hotel is the city’s first hotel built to meet the Leadership in Energy and Environmental Design (LEED) Silver rating from the U.S. Green Building Council. Which means we could count on some fabulous bath products (hello H20 Organics!). And the fitness center, 32″ flat screen TV and free wi-fi came in handy when Mother Nature decided to rain on our vacation parade.

Dinner on our first night was at the hotel restaurant, Elate. We weren’t quite hungry and were a bit tired, so we decided to graze on a few small plates, in true New York style. Two stand-out dishes were the Ruffles & Truffles, homemade potato chips with a chive and truffle cream dip, and the Butterfinger Pot de Creme for dessert. The restaurant was beautiful with floor to ceiling windows and a super friendly staff. I definitely recommend Elate even if you’re not staying at the Hotel Felix, if just for the pot de creme. Our evening continued with a fabulous bottle of champagne at Pops for Champagne, a champagne bar on the North Side, a fantastic Chicago staple offering up a perfect way to celebrate some much needed time away from home. While heading uptown to Green Mill Jazz Lounge, which comes highly recommended by locals, we met some Cubs fans headed to Wrigleyville to celebrate the team’s win that evening. While not the biggest baseball fan, I did find the prospect of some all-American quality time with the locals extremely intriguing. Wrigleyville is the perfect place to get a taste of the dive bar and locals scene in Chicago, where the true Mid-Westerner in the city-dweller really comes out. The scene was different than New York, everyone was about celebrating the Cubs win and enjoying $2 beers and tacos with friends instead of spending the evening on the prowl, hoping to meet prince charming.

The Architecture River Cruise is 90 minutes worth of historic sights and facts

After a peaceful sleep on our bed of clouds, we headed to lunch at The Signature Room on the 95th floor of the John Hancock Building. As I mentioned before, the weather was a bit gloomy and the walls of tall windows were entirely covered in fog. So much, in fact, that some guests were asking the management to pull up what they thought were the curtains so they could see the view! The fog did manage to clear by the end of our lunch. We enjoyed a delicious meal from their lunch buffet, with a hearty soup, and some perfectly sauteed broccoli rabe. Our server, Brian, was extremely charming and attentive and even let us do an entire tasting of all of their delicious sorbets for dessert. The view was breathtaking, water for miles alongside skyscrapers. Very reminiscent of New York, but rarely do you get the option to view the city that way.

We intended on spending the day shopping and sightseeing but instead got caught in a monsoon rainstorm and had to head back to the hotel for cover. Naps are always an important part of vacationing. For dinner, we found ourselves at Rockit Bar & Grill, a causal, locals spot fully equipped with extra large margaritas and menus emblazoned with Rod Stewart’s face. Their burger was juicy and delicious and French fries perfectly crispy. Dessert is a blur as I couldn’t remember much after my third margarita. We turned in early that night after a stroll around town, enjoying the rain-less night.

Our final day in Chicago started with a delicious meal at one of my favorite restaurants ever. Frontera Grill, owned and operated by Rick Bayless, one of the top chefs in Mexican cuisine. Enter margarita #20 (a slight exaggeration?), molcajetes full of freshly made guacamole and tortilla chips and a table crowded with pulled pork, shrimp and chicken tacos. We left stuffed to our heart’s content and headed to the Michigan Avenue Bridge for a 90 minute long Architecture River Cruise along the Chicago River courtesy of the Chicago Architecture Foundation. We learned about the tragic Great Chicago Fire, which wiped out about four square miles of the Chicago but made way for the beautiful modern architecture that adorns the city today. We sipped hot chocolate on the brisk Thursday evening and soaked up all of the beauty that you take for granted as a city resident but adore as a tourist – much like life in NYC.

Green Zebra, Noble Square’s vegetarian restaurant

The evening cruise was the perfect prelude to our favorite dinner of the vacation. Green Zebra in the city’s Noble Square neighborhood. This small-plates vegetarian restaurant satisfies even the biggest meathead. Think the freshest, most seasonal ingredients used at the peak of their season for optimal flavor. Though the menu changes frequently to accommodate the freshest fruits and vegetables, we enjoyed a hearty onion tart garnished with diced summer squash and zucchini, crunchy bok choy and a salad of carrots and ginger sorbet. For dessert, we died and went to heaven with crispy, cinnamon-sugary wontons stuffed with banana and mini ice-cream sandwiches filled with coconut, chocolate and (my personal favorite) peanut butter ice cream. The perfect meal to end a perfectly relaxing vacation.

To answer that burning question – does it really feel like a vacation if you visit another major city – I say yes! While on home turf, we never take time to enjoy all that our wonderful city has to offer, maybe in an attempt to not do anything the least bit “touristy.” But while on vacation, you spend time exploring and learning about new places, enjoying meals at restaurants you’ve never been to before. You take naps at 2 o’clock in the afternoon, because…well…you can. So I say, a vacation is a vacation, no matter what your destination is. The only rule of thumb is to relax. Leave your crazy New York life behind you for a week and enjoy life’s little pleasures like hot chocolate on boat down the Chicago River, tacos created by at top chef and running for cover night after night from the unforgiving rainstorms until finally giving up and embracing it!

Originally published November 2009



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