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First timer in the Windy City

TravelLucy LopezComment

Imagine the night before your flight, your stomach in excited knots because it feels like Christmas already. There's nothing comparable to a trip with friends to explore a new city. That's how I felt on Friday Nov. 20.

Simply starting with a text, "do you want to come to Chicago?!" My best friend Kait and her fiancé Moe planned a spontaneous trip and another friend, Brittany, was planning to tag along too. One thing led to another and I got to join in on the exploring. 


WWD: What we did

After an hour train ride into the city from O'Hare, we checked into our hotel, The Wyndham. Our walk from the station was flooded with huge buildings, a pretty view of the river, and crisp Chicago air. After check-in (they got us in early thankfully!) our only concern was FOOD. It was around 11 A.M. we decided to go to Yolk. Moe had been there before and said it was good, he was definitely right!

Once fed, and all hilariously hangry moods aside, it was time to be tourists. We hopped in an Uber and made it to The Giant Bean. Seeing so many people frolic around this giant mirrored structure, taking photos, their eyes filled with pure awe and happiness, made it kind of fun to be a tourist. This is probably the only time I would've loved to own a selfie stick! 

On our Uber to location two, my stomach started to get butterflies. I was mentally preparing for the Skydeck at Willis Tower. Though I didn't look down, stepping out into that little glass box required a deep breath (or three). We got our iconic "sitting on the glass" photos, though Kait got a little freaked... she looked down when she sat down! 

After a quick shopping stroll on Michigan Avenue and a well-need siesta, Friday night concluded with a night out at Henry's and a pizza pan size of nachos. I wish it hadn't been too dark for a picture, but let's just say when they say giant, they mean it. 

Saturday we kept things pretty relaxed. Brunched again, this time at Wildberry Cafe, shopped on Michigan Avenue again (because Uniqlo & Zara are obviously destination shopping), and ended the night with a late dinner at Hub 51. We planned to ice skate but Saturday night's cold was a bit much. I'm a Buffalo girl and used to the cold but I was so not ready for a real-feel of 10 degrees.

We definitely got our taste of winter in Chicago. With all the Christmas decorations going up and crowded streets with pedestrians singing carols to stay cheerful in the frosty air, I definitely got into the holiday spirit! 


WWA: What we ate

Wildberry Pancakes and Cafe

YOLK: As a creature of habit I got eggs benedict for brunch but what stood out was the home fries! I love when breakfast spots use red potatoes. Big portions, so if you're hungry like we were this is a good place to go! 

HENRY'S: Did I mention their nachos were giant? Their name doesn't lie! Upon five or so minutes of going in, we saw someone get nachos and that's all we could think about! We were here for our first night out and it was a nice relaxed vibe with a pool table, large bar spanning the length of the space, and a layout ready for good conversation. 

WILDBERRY: This place is definitely a hot spot. We had around a half hour wait, with no space to stand in their small entryway, needless to say that led to a photoshoot outside. I had eggs benedict, again, and chocolate chip pancakes on the side. WHO DOESN'T WANT CHOCOLATE CHIP PANCAKES ON THE SIDE. My sweet and savory cravings were satisfied. To the right you'll see the massive amount of food we got. 

HUB 51: After yet another well needed siesta, I went on good ol' Yelp to find this. As soon as I saw the variety, I knew it'd be the perfect place to cater to our individual tastes. Together we got a combination of sushi, a burger, arugula salads with salmon, and delicious guacamole. It was also super nice inside, industrial but warm design. 

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WWW: What we wore

"The cold never bothered me anyway." 

You could say Elsa would have been proud of us. Thanks to lots of layers we didn't freeze and, to be honest, it was actually kind of fun to be bundled up! Oversize scarves saved us, literally. 

I am so happy I went coat shopping before the trip, though I was still be able to wear my trench coat with thermal leggings and wool socks for extra warmth! And what's better than going on a trip with friends who all relatively wear the same size as you? Nothing. Absolutely nothing. Triple the wardrobe and accessories!

Quick tip: Ski leggings keep you extra warm for winter. Combined with wool socks I was so cozy! 

Quick tip: Ski leggings keep you extra warm for winter. Combined with wool socks I was so cozy! 


Flights home after a weekend trip are bittersweet. My next time will definitely need to be longer.  Two days in the Windy City and I think it bumped New York off my number one favorite city spot... okay, maybe they're tied.

It was fun Chicago, I'll see you soon.

Let the adventures continue.

• UNTIL NEXT TIME •