A Quick Trip to Chi-Town

Dear Chicago. I love you. 

On Sunday morning, I landed in O’Hare International Airport and by noon I was smitten with Chicago. This city is simply stunning. Each and every piece of this architectural puzzle compliments the other and is guaranteed to take your breath away no matter what direction you look. But seeing as I naturally gravitate to the water, I may be a little biased to the East.


I started my journey by checking into The W Hotel- Lakeshore, where I dropped off my bag and met with Quincy, the concierge. In no time, he had me well acclimated to my surroundings and provided some helpful key points of interest.

Millennium Park was my first stop. I wandered around, smiled at strangers, people watched and then questioned how I had yet to stumble upon The Bean. So I typed “The Bean” into Google Maps, to quickly realize it was just a few short steps away. At that point, I decided I wouldn’t rely on my iPhone to get me from Point A to B. My time with Quincy was well spent and I was more than capable of figuring it out as I wandered about. And that I did.


Although I was advised by a couple of Chicago transplants back home against it, I took a few totally touristy selfies. 

Like NYC, Chicago is a giant grid. Familiarize yourself with key streets and landmarks and you’re good to go. Plus Michigan Avenue is hard to miss and is basically the spine of the city.  

After Millenial Park, I headed to the Architecture Boat Tour on Chicago’s First Lady. This tour provides a true taste of the intention behind the most famous buildings in the city. I left feeling like I had a better understanding of the skyscrapers surrounding me and the history their walls have witnessed over the past century, even more so than the city I call home.

Lake Michigan is no joke. Unlike the Hudson and East Rivers, where I would never be caught dead in a kayak, the water sports and activities here are in full force.

There was no better way then to close out my first day here than with a Lou Malnati’s Deep Dish Pizza. Although I ate like it was, this wouldn’t be my last encounter with Chicago style pizza.

Turns out that Chicago isn’t just great at the deep dish. They are also pretty spectacular at specialty pies too. I ate more pizza on this trip than I did as a senior in college. And we ate A LOT of pizza in college.


Typical Monday nights aren’t very exciting. But my Monday night in Chicago was the best night of my trip. Mainly because I spent it at a Cubs Game and it ended with what else, moreeee pizzaaaa! Wrigley Field was so great that it even made eating sunflower seeds satisfying. In any other venue, they are most certainly not worth the trouble. The video below details my first hand experience learning how to eat sunflower seeds. Sorry in advanced. I have sworn to stick to peanuts instead.

After several attempts at starting “the wave”, catching balls and eating more sunflower seeds, I looked around the stadium and thought to myself, “I am so happy.” Everything about that moment, this trip, that day, and this city, encouraged me to simply feel fulfilled. I love the Cubs and all that encompasses Wrigley Field. This stadium and those who fill it are inviting, friendly and down right fun. I am officially a Cubs fan. Sry Yanks.


Although the Cubs didn’t win, the stadium stayed full until the very last inning. I’m sure it helps that there’s no annoying commute home like the fans of our New York based teams are forced to endure. But it felt like there was more love and respect for the players and people here and that maybe a miracle might just happen at the last possible second. And when it didn’t, we dealt with our emotions the best way we know how. Pizza.

From left to right: Nacho Slice; Spinach, Mushroom and Roasted Pepper Slice; Tomato, Spinach and Feta Slice
Pictured above is our late night pizza party post Cubs Game. We think we picked up these sexy looking slices at Big G’s right by the stadium, but no promises. At this point I was exhausted from all the bleacher creature commotion and was a few beers deep. Although these slices were insanely delicious, the dirty water dogs and Goose Island 312’s while posted up in the bleachers at Wrigley Field, were still a bit more satisfying. But hey- it’s not really a fair comparison.

Continuing with the food scene here, I doughnut even like doughnuts that much but Doughnut Vault came highly recommended. So I gave it a whirl. And let me tell you- doughnut disturb me while I’m eating my Ginger Bread Stack. Because that cakey goodness takes up all of my attention. They were just the right amount of sweet and doughy.

Dinner on day two was at Monteverde. This place is known for their homemade pasta but everything we ordered was insanely delicious. We started with the ricotta and artichoke crostini’s sprinkled with flakey truffles then moved on to the green salad and broccoli rabe. After all of that, I still managed to eat my homemade Cacio e Pepe main course plate clean. The portions here couldn’t have been more perfect and the food itself is both mouth watering and mind blowing. And the breadsticks. Don’t even get me started on the crispy breadsticks! I wanted to stuff the few that were left in my bag for later. Don’t worry, I didn’t. But I really wish I had…

I am already thinking about how and when I will be able to come back here. If I could eat this meal everyday, I would be a very happy girl.

My last stop before heading back home was for the best burger in America at Au Cheval. And it most certainly did not disappoint. This burger was bad ass and now ranks as my #1 favorite. Decorated with a bright sunny side egg and crispy slab of bacon, this burger is sure to be as messy as it is delicious. I thought I’d be safe to indulge but turns out I made friends at the bar which encouraged me to keep it as clean as possible. Two cloth napkins and friends later, I slid into a food coma and headed to the airport.


I would totally contemplate moving here if it wasn’t for the intense winter months. So instead, I’ll just plan to visit again in the summer time. A big thank you to all of the new friends I made in Chi Town for making my quick trip so memorable. When exploring a new city, it pays to keep your eyes up and your heart open to trying new things. I promise, you won’t be disappointed you did.