Avid traveler, and travel writer, Stephanie Bonilla returns to share her experiences from a recent Chicago visit. Many of our cruisers are from the Windy City, so we are delighted to share this contribution!

I finally booked my trip to Chicago after catching myself constantly looking up airfares from Miami to O’hare. It seemed I was on a subliminal mission to check the ‘windy city’ off my wanderlist. On a celestial Wednesday night, the stars aligned and I was able to find an extremely cheap flight just in time for Labor Day weekend.

Something about Chicago has always fascinated me. There’s something to say about a city whose endured so much (the Great Chicago Fire, every single winter ever) yet prevails year after year, never falling short of any “best cities to live in” list. Every Chicagoan I’ve ever talked with describes how miserable and brutal the weather can be, yet follows up his/her complaint with numerous ways the city blossoms during summer. For only three fleeting months of awesomeness, locals willfully withstand six months of snow storms and insanely cold temperatures. The only other city that comes to mind that houses such a loyal fanbase is NYC, where every winter becomes an obstacle of the spirit for its inhabitants. But why? What makes Chicago the outlier of the Midwest? I was determined to find out.

Friday

After taking the earliest flight out of Miami possible, we were checked in and ready to sight-see by noon. Chi-town is an extremely walkable city, allowing visitors to embark on their respective journeys via foot (or by purchasing a Ventra Card). We quickly made our way to Wild Berry, conveniently located on the outskirts of Millennium Park. The restaurant’s ‘Creamy Nutella’ crepe, which comes sprinkled and stuffed with chocolate drizzled banana goodness, is one of the many delectable dishes diners can choose from. Fall where you will on the brunch debate, this place won’t disappoint. We used our sugar buzz to take on Millennium Park, making it in and out of the park in about an hour and checking out its impressive amphitheatre and infamous Cloud Gate sculpture along the way. It seemed like everyone was out enjoying the summer’s heat, with herds of joggers and cyclists invading the park’s grounds. I started to see why Chicago’s residents are so bewitched by their city.

After wandering around the park’s surrounding area, we hopped on a train and headed to Goose Island Brewing Co., the masterminds behind one of my all-time favorite beers, 312. Although we didn’t make it to the walking tour, we sat in the brewery’s tap room for quite some time. Pint after pint, our buds were awakened with a mix of tasty ales. Already in the beer spirit, we took a train to Rock Bottom Brewery, a brewpub designed with beer enthusiasts in mind. Every craft-beer served at this pub is truly a labor of love. After trying a couple of brewskies and wallowing in the pub’s pungent hoppy aroma, we somehow stumbled back to our hotel to change in preparation for our evening plans. Volare was what was for dinner and marked the perfect ending to our eventful day. This gem should be on every restaurant list published about Chicago.  In fact, any lists printed prior to the opening of this restaurant should be required to be republished. If you like authentic Italian cuisine intertwined with a romantic ambiance, make sure you add this to your itinerary. Reservations are a must, unless you’re cool with waiting an hour or two for a table.

 

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Saturday

After having such a great first day in Chicago, Saturday had big shoes to fill. We started our morning by visiting the Willis Tower. There is so much to see here, particularly the sky deck that offers spectacular views of the city. If you’re brave enough, you can stand on one of the glass boxes that extend 4 feet from the deck, leaving you floating 1,353 feet up in the air. It’s truly a gnarly experience. After experiencing such an adrenaline rush we decided to indulge in some emotional eating. Fortunately, Giordano’s, Chicago’s famous deep dish pizza eatery, was just a few steps away. It takes around 45 minutes for the restaurant’s pizza artisans to work their magic, but the final masterpiece is worth the wait.

We embarked on a 75-minute Wendella Architecture Tour later that afternoon, learning about Chicago’s glittery skyscrapers and the history behind the city’s remarkable transformation. This tour is a must for design and architecture buffs, allowing passengers to see Chicago in a truly unique way. Once the tour was over, we treated ourselves to more food and drinks at a near-by gastropub called Public House. With a mixed crowd of yuppies and hipsters, this place has an awesome, laid back feel and some really good nachos.

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Sunday

Sunday started as quickly as it ended. Inspired by the city’s abundant energy, we decided to run to Lincoln Park, through the  Lincoln Park Zoo, over to Lake Michigan, stopping to gaze at beautiful brick houses along the way. We were famished by 11:30 a.m., making it back just in time for our brunch reservation at Hutch. From their pulled bacon Benedict to their jalapeno and garlic infused cocktails, this place knows how to fusion. Named on many of Chicago’s “boozy brunch” lists, seating at this restaurant comes much slower than it goes.

We rolled on over to Wrigley Field after brunch, the legendary home of the Chicago Cubs. If you’re visiting during baseball season, I encourage you to buy tickets to a game. Chicago fans are no joke, wearing their royal blue and red jerseys with pride.  Following a big win against the Arizona Diamondbacks, we made our way through the rowdy crowds, seeking shelter at Emporium Arcade Bar, an adult playground come to life.  If you could get your hands on any of the 400 machines found in this ‘barcade’, you can play Ms. Pac-Man while sippin’ on your PBR(s) and jammin’ to awesome tunes. The rest of the night is a little hazy, but I vaguely remember bar hopping and fireball shots being involved.

Monday

We attempted to cure our hangover with sunshine and the consumption of a lot of comfort food. Yolk offers a great food selection with more than just eggs on their menu. They’re known for pushing the envelope with creative breakfast and lunch items which include: scooped out pineapples filled with housemade Greek yogurt and fresh fruits or tasty Red Velvet FrenchToast.  Soon after eating and sipping on some much-needed coffee, we took Uber to Chicago’s landmark, Navy Pier. After taking a ride on the pier’s iconic Ferris wheel, our time left in Chicago was quickly approaching its end.

Our last stop on our trip was Lagunitas Brewing Company. Because why not get over a hangover at a brewery, right? Although the location is a bit rough around the edges, the facility’s size and interior more than make up for the sketchy locality. Be prepared to walk through many trippy hallways blasting Alice and Wonderland tunes.  Afterall, this is the headquarter of a beer-maker that believes the golden hued liquid they discharge out of a tap is the answer to social intercourse. My favorite part of Lagunitas, or any brewery for that matter, was their tap room. We sent our amazing long weekend off with lots of clinks of our Hop Stoopids and Sucks, a reference only true beer fans will understand.

‘Til next time, Chicago.

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