Chicago: A Review

When I was first making the leap to move to a big city about five years ago, I was choosing between Chicago and New York City. I had new friends from Birthright that lived in both, I was eager to make a huge change in my life, and I knew that either could provide me the opportunity and adventure that I was seeking. It was my mom that encouraged me to go for NYC, making a good point that Chicago is very livable at any age, but that New York is best enjoyed when young and so I went for it. 

When I visited Chi the first time, it was January so it didn’t even reach zero degrees, plus I had just dropped out of grad school so I had negative money and couldn’t really enjoy it. The next time was about a year later, did some fun tourist things but still didn’t have much cash and so we did everything that was cheap. 

I just spent a long weekend in this lovely Midwest metropolis visiting my bestie, and this time was much different than the last. I got to experience the life of an uptown Chicagoan, hanging by the lake, snacking on some tasty things, exploring fabulous bars, and enjoying a new concept called a “progressive dinner.” And now I will tell you about some of the magical things I ate, because that’s what you’re here for, right? 

Cafe Baba-Reeba 

Get this. In Chicago you can go to happy hour, split 2 pitchers of sangria and about 10 plates of tapas for 4 people and only rack up $80. WHAT A CONCEPT. This place was everything we needed it to be. The sangria was delicious, the tapas were hot off the grill and so tasty (and extremely cheap), and the bartender had us cracking up in about five minutes. We planned to stay for about an hour and ended up there for almost three. What else could you ask for? 

Klein’s Bakery 

First of all, what a cute little spot. They have indoor and outdoor seating, lovely baked goods, and a really delicious blueberry iced tea. After much deliberation, I selected one of the puff pastries, stuffed with cream cheese, spinach, and ham, and sat myself outside to answer some emails on the most beautifully sunny, cloudless day. 

Hot Dog Fest

Yeah, there’s an entire festival dedicated to hot dogs, one of my favorite foods. Just picture my excitement, I couldn’t contain myself. We did a lap to get a rundown of the options, then decided we’d split three dogs plus an ear of elote. The initial dog was called the Midway Monster which had BBQ sauce, cheddar cheese, bacon bits, and giardiniera peppers (a fantastic condiment made of spicy and mild peppers that everyone should try.) Next was a classic Chicago Dog. To be honest, it was kind of disappointing because it had a regular bun rather than a poppy seeded on and the slices of tomato were enormous which caused a strange distribution upon biting down. However, a good quality Chicago Dog is better than no hot dog so I was pleased. And finally, we had a guac dog topped with fresh guac, spicy mayo, roasted poblanos and cheddar cheese. The stomach ache that ensued was definitely worth it because I just really, really love hot dogs. 

Happy Camper

Easily one of the coolest bars I’ve ever been to. It’s mostly outside but has covered areas that feel indoors yet with a breeze. The drinks are unique and delicious; I had a “Trashy Tea” which is a can of Brisk with a little Deep Eddy Lemon airplane bottle tipped in, and then a “Pink Flamingo” which was like a spicy margarita. NOM. Then we split Goat Stix which I mistakenly thought were stuffed with goat cheese (I’m sure you can imagine my disappointment) but were actually just fluffy breadsticks that we dipped in a sauce made of goat cheese and marinara. Yeah, I know, it was as fantastic as you’re imagining it. But the real beauty was the pizza. It was like a hybrid of NY style and deep dish with a super fluffy crust that had a little chew to it and piled high with toppings. Mine had huge cloves of perfectly roasted garlic, artichoke hearts, basil, feta, and olive oil. I kind of wish I didn’t eat it on the same day as the hot dogs because my appetite wasn’t as huge as it could be, and we did leave the leftovers out on the counter all night which was devastating but honestly, it was all worth it. So, so worth it.

D’amato’s Bakery

On Saturday, we did this awesome “progressive dinner” concept with my friend’s entire family. We started at her condo, had some tasty chocolate and beverages, then took a party bus to her cousin’s place where we had more appetizers and their family’s signature drink. Next was a different cousin’s massive apartment with a gorgeous roof where we were served margaritas and a taco bar. We finished the evening at someone else’s apartment where we had even more alcohol (yes, I know) and this amazing tray of desserts including huge cannolis capped with chopped pistachios on the ends of a fabulous vanilla pastry cream. Each one was so indulgent I couldn’t finish it by myself so I had to split it with someone. They. Were. Epic. 

I obviously didn’t do the tourist things like Lou Malnati’s deep dish or Garrett’s popcorn, mostly because I’ve had them before, but also because I love to experience a city through the things locals love. Even if I don’t have friends to show me around, I find it much more validating to find the funky things, the places off the beaten path, the family favorites. I highly recommend it; you never know what you’ll find!