“You wake up in Chicago, pull back the curtain and you KNOW where you are. You could be nowhere else. You are in a big, brash, muscular, broad shouldered motherf***in’ city. A metropolis, completely non-neurotic, ever-moving, big hearted but cold blooded machine with millions of moving parts — a beast that will, if disrespected or not taken seriously, roll over you without remorse.
It is, also, as I like to point out frequently, one of America’s last great NO BULLS**T zones. Pomposity, pretentiousness, putting on airs of any kind, douchery and lack of a sense of humor will not get you far in Chicago.”
Anthony Bourdain (one of the great loves of my life) wrote that, not me. And he’s right.
I wasn’t expecting to fall in love with Chicago, but I did. There’s something special about walking in downtown, with the Chicago River snaking through the city and its towering skyscrapers.
Thanks to easy public transit, renowned museums, and an incredible food scene, I got the perfect taste of the Windy City in just four days.
Side note: I was visiting one of my dear friends, so when I refer to “we” in this post, I’m referring to Jo!
Where to Stay
I stayed at The Robey in Wicker Park, which is an excellent neighborhood to experience the spirit of Chicago. Plus, the train station is nearby, so you can easily hop on the ‘L’ train to get to downtown.
Dine at Cafe Robey (they serve all-day brunch) and visit The Up Room for cocktails and panoramic city views.
Cross your fingers and toes that you get a room with a view because I got to witness Chicago’s first magical snowfall of the season, and it was extra special to see the city streets layered with puffy snow.
Where to Eat
I ate my way through the city and never had a bad meal. Chicago is known for staples, like deep-dish pizza and dipped Italian beef sandwiches, so you know I had to do some investigative work! Here are my favorites.
I accidentally stumbled into Dove’s because it was close to my hotel. Let me just say, I was so bummed I discovered it on one of my last days because I would have totally brunched there every morning.
It’s a 41-seat diner where you can eat some tasty Southern-inspired Mexican dishes while listening to vinyl records. The highlight for me wasn’t just the delicious food, but the bartender’s energy. His name is Courtland, and he is one of the coolest people I’ve encountered. You can tell he loves what he does. The man knows how to spin that jukebox and mix up some bomb cocktails for folks.
This neighborhood gem in Logan Square also offers dinner, but my friend and I enjoyed a phenomenal breakfast burrito there. I can’t stop thinking about its soft scrambled eggs, which were cooked to perfection. Also, the green salsa goes hard.
After dining here, I went down a rabbit hole and learned that its Chef and owner, Jason Hammel, is actually self-taught. He wanted to be a writer, but discovered his passion for food after traveling to Italy and staying across Florence’s central market. It’s really no surprise that Lula Cafe is at the forefront of the farm-to-table movement in the Midwest. As a farm-to-fork girlie, I approved.
The food blew me away, so of course I had to pick up The Lula Cafe Cookbook: Collected Recipes and Stories. If I were a book cover, I’d be this one, obviously.
I made his Brussels sprouts salad with cashews for Thanksgiving. It only took me 4.5 hours and a few tears, but oh my goodness, it was unreal. Who knew a fish sauce and lime vinaigrette paired with cashew sauce is the perfect combination?!
the salad I made!!
Pequod’s is a vibe. The space feels like an old neighborhood bar with zero pretentiousness.
They’re apparently known for their caramelized crust, which gives the pizza a crunchy texture. You can also go crazy with your own toppings, so have at it. I’m not the biggest fan of deep-dish pizza, but I still enjoyed my slice.
There are so many deep-dish pizza places to choose from, so you can go on a mission to find YOUR favorite slice. My other friend from Chicago also recommended Lou Malnati’s and Giordano’s. I enjoyed Lou Malnati’s pizza because it has a thinner, flakier crust, and I’m just used to that. Chicagoans, I’M SORRY.
Experience old-school Italian cooking and martinis here! I sat at the bar and relaxed in the mid-century-themed atmosphere. Come hungry because the portions are huge. I had their 8 Layer Eggplant Parmigiana and then ended the night with their homemade cannoli and a shot of espresso.
As a foodie who is also a sucker for a dimly lit ambiance, dining at RL did not disappoint.
The interior felt like I was in some upscale and exclusive Upper East Side cigar lounge or old-school library. The walls are covered in beautiful paintings, and leather accents can be spotted left and right.
Service was great — thanks to our waiter, we learned it’s a must to check out their bathroom downstairs. He knew the girlies needed a selfie in RL’s elevator.
obligatory elevator selfie. outfit details: Sézane sweater, Free People trousers, Uniqlo bag.
There are so many of these. It’s a fast food restaurant that knows how to run things. I inhaled their Chicago-style dog. I didn’t get their Italian beef sandwich, but they apparently deliver nationwide, so I might treat myself to one!
still thinking about that glazed cinnamon roll on the right
I could see this place from my hotel room and the line of folks waiting in the cold never died down. I had to see what the hype was all about. I am still thinking about their cinnamon roll! SO DELICIOUS.
Where to Explore
The Art Institute of Chicago (AIC)
Lots of bangers here. I was very impressed by their thorough Impressionism collection.
This is an excellent way to learn more about the history of Chicago. I recommend booking a tour on a day when it’s fairly sunny, since the best way to take in the city is from the boat’s deck.
There are several companies to choose from, but the Chicago Architecture Center (CAC) tour was highly recommended to me by many. Plus, the CAC docents are expertly trained and provide knowledge about architectural styles. The boat will go through all three branches of the Chicago River, and at the end, you’ll get to see a stunning view of Lake Michigan.
Frank Lloyd Wright Home and Studio Tour
Continue looking at architecture by visiting the home and studio of Frank Lloyd Wright. It’s in Oak Park, which is a charming area that is also home to the birthplace of Ernest Hemingway.
On the Frank Lloyd Wright tour, you’ll learn all about the Prairie architecture style. You can also tour other Wright-designed residences nearby.
Where to Shop
Browse through new and gently used books at this gem. Photography is prohibited here, but I sneaked a picture for my blog. What can I say, I’m a rule breaker.
Super cute store with many trinkets and gifts for any occasion (they were already decked out for Christmas!). The shop carries antique home goods and vintage goods sourced from auctions and European flea markets.
peep the Lula Cafe cookbook
A dope woman-owned business. Their mission to support independent artists and makers is crystal clear. You can find anything here, from pantry items to artwork, clothing, etc.
Lots of vintage clothes to peruse through. This place started out as a market and eventually opened up its flagship shop in Wicker Park! Make sure to take some photos in their vintage photo booth in the back.
Where to Hang Out
Walk through the park, people watch, and see the iconic Cloud Gate, aka “The Bean.”
3 Arts Club Cafe at RH Chicago
You can peruse the store, dine in the gorgeous courtyard, or grab a coffee from their cafe and rest and relax in a cozy corner.
Wicker Park
I’m biased because I stayed in Wicker Park, but I truly enjoyed this neighborhood. It’s wonderful and walkable. I would totally live here.
Milwaukee Avenue is filled with so many unique small businesses (some are mentioned in ‘Where to Shop’), but if you need your big brand fix, you can always pop into the Levi’s Store or even Salomon off of N. Damen Avenue. The options are endless.
The neighborhood is also very close to Ukrainian Village, which I had to check out. I did enjoy some potato and mushroom dumplings at the Old Lviv Restaurant. ❤
Chi-Town, you stole my heart. Weirdly, it felt like home. It might be because, as a kid, I was obsessed with Kanye West’s song, “Homecoming.” Absolute banger of a tune, and it hit different when I was there.
But I think it felt like home because one can live a hustle-bustle life here, yet still feel grounded. People seemed passionate about what they do, and they felt real. I guess I want to be where there’s some realness and edge.
Until next time, Chicago! xo
Where should I go next?!
torimuser 
Great post, and a fun read too Tori! The pecan-packed cinnamon roll from Mindy’s looks delectable!
LikeLike
thank you, Monch! RIGHT?! i wish i could’ve tried more things at Mindy’s!!
LikeLiked by 1 person
If I was there, I’d definitely have it with a regular black coffee!
LikeLike