How To Spend Four Days in Chicago

Hey everyone! I hope you all had a great long weekend. As you may have seen on Instagram, I was in Chicago this weekend with my mom. And I'm here to recap our girls weekend for you! 

Why Chicago?

Ever since I came back from Europe in January (read about that trip here), I've been wanting to travel again. That's the thing about traveling—the more you do it, the more you want to do it. At the beginning of the year I made a dream destination list of places I wanted to go and Chicago was at the top of the list. It's a two hour flight from NYC and it has such a cool art scene, great restaurants, and beautiful architecture. I'd say about once every four years I take a true vacation-vacation (you know, sitting on the beach, G&T in hand) because for the most part I want to be constantly exploring and on the move, so cities are my go-to destinations. I hit up my BFF (hi mom) to ask if she wanted to join me and she said yes! Plus, she let me plan the whole trip and didn't complain when I made her take photos of me, so needless to say she was a fabulous travel companion. 

What I Packed

I will be the first to admit I am not a light packer, but I was super impressed with how I did on this trip! Here's what I brought along in terms of clothing:

Jackets: black leather jacket, white bomber jacket

Tops: black off-the-shoulder top, pink blouse, white T-shirt, striped T-shirt, mesh floral top

Dresses: little black dress

Jeans: black skinny jeans, blue distressed jeans

Bottoms: denim mini skirt, black cotton pants

One-Pieces: patterned romper, black jumpsuit

PJs: T-shirt and running shorts

Shoes: black and white sneakers, black patent boots

Extras: makeup bag, curling iron, toiletries, computer, camera, umbrella

And that's it!! Not bad for an over-packer. To see more photos of my outfits, check out my Instagram

Day-by-day breakdown



We took a mid-day flight from NYC and landed in the afternoon, which left plenty of time to explore that day. We headed over to our hotel in the River North neighborhood. After we checked in, the obvious first task was to find deep dish pizza. Thirty minutes later we were at Lou Malnati's—they're known for their buttery crust, and even though they're a chain I can promise you they're the real deal. We walked along Magnificent Mile (picture 5th Ave) and through Millennium Park, home of "The Bean," which is actually a sculpture called "Cloud Gate" made by British artist Anish Kapoor. One of the biggest mistakes I've made when traveling in the past was not allowing enough downtime to get a little lost and explore to see where the day takes you, so I wanted to make sure this trip had lots of room for that. For dinner, we met one of my best friends from high school, Nicole, at a restaurant called The Hampton Social. I actually went back to this place for brunch on Sunday because I was so obsessed with it. The food was fabulous, and the atmosphere was adorable. If you're ever in town, definitely check it out. 


I decided Friday and Saturday the days where we'd pack in all of the must-see sights. I had been told by several Chi Town experts (my friends and Chicago-based bloggers I DM'ed on Instagram) that I had to check out Wicker Park, a neighborhood that definitely had some Brooklyn vibes going on. We popped in and out of some shops like Myopic Books and Moon Voyage before heading over to Big Star for tacos and margaritas. My favorite taco that I tried was called "The Walkaway" which came in a Fritos bag, with the Fritos acting as the tortilla. The margaritas were also heavenly (we both ordered seconds). We got a corner table just as the sun came out—talk about perfect timing! In the afternoon it was off to the Museum of Contemporary Art, which has some really cool exhibitions up right now, like "Eternal Youth." I am tempted to come back in June because they'll have a whole show for one of my favorite artists, Takashi Murakami. We went to Eataly for dinner and after I met up with my friend Selena, who I worked with forever ago at Free People, and her friends. We went to Headquarters Beercade, which had tons of free arcade games, great beer, and an abundance of Instagrammable neon signs. Definitely a fun place for a night out here. 


On Saturday we started off by hitting up probably one of the most popular things for tourists to do when they visit the Windy City: an architecture boat tour. We did ours through the Chicago Architecture Foundation and it was absolutely awesome. Originally the weather had predicted thunderstorms and when we woke up it was 75 degrees and sunny. Our guide knew every building inside and out, and there was even free lemonade and cookies on board. The whole tour took 90 minutes and since we opted for the 10 A.M. one, that left plenty of time for brunch after. We found a place super close to our hotel called Bridge House Tavern, which is right on the river and has $5 mimosa and bloody Mary specials on the weekends. Then it was off to The Art Institute of Chicago, which I've wanted to visit since I found out it existed. My mom swooned over Monet and Renoir while I got swept up by Judd and Mondrian. The Institute is right across from the park, so we went to enjoy the beautiful day (and I met up with Nora, who I can't seem to go anywhere without!) For dinner, we got to catch up with my cousin Meaghan who I haven't seen in forever over gnocchi and wine at Siena Tavern. It was so good to see her and hear about her life!


The weekend flew by! I couldn't believe that Sunday had come so fast. We had an afternoon flight so when we woke up we were debating where to feast on one final brunch before heading back to New York. We couldn't help but notice the menu of The Hampton Social pop up as we were scrolling through OpenTable. Why mess with a good thing? We happily went back to the adorable eatery and had lobster B.L.T.'s (my new favorite dish) and enjoyed a breeze coming through the open windows, and live music. Afterwards we headed back to the hotel where I wrote part of this post while sitting outside on the patio with a view of the river. It felt like the perfect last moment of the trip. Fast-forward a few hours later and we were back in New York. 

Photos by my mom, Nora, and me

And that's it! I am already mentally planning where I want to go next. I realized that I've now been to 17 out of 50 of the United States and I hope to do all 50 in my lifetime. One of the best parts of this trip was that I realized that I really do have friends everywhere who can recommend fun things to do, offer a couch to crash on, and who can show you a good time in an unfamiliar place. It makes traveling so much easier—and way more fun—when you can do it with awesome people.

Have you ever been to Chicago? What are some of your favorite places?