The Windy City has plenty to offer, especially during the holidays with fun displays full of festive cheer. From art and shopping to food and culture, there is so much to enjoy! I recently got my city fix in for a weekend, and it was honestly the perfect little itinerary for a short and fun getaway. While I am nowhere near an expect on the city, here is where I suggest you eat, shop and explore in Chi-town.
The Magnificent Mile on Michigan Ave is the place to go for shopping in Chicago. Being one of the most famous streets in America, the glamour doesn’t disappoint. Glitzy designer flagships align the street among large global chains and huge department stores, meaning there is something for everyone. The window shopping is first class too! For the holidays, the street is all decked out with fun little displays outside, in addition to amazing window decor from the designer stores. I was there on Black Friday, and although crazy, the hustle-like atmosphere from the crowds was exciting and exhilarating, almost like out of a Christmas movie. All of the department stores are worth checking out and, while not as large as their NYC counterparts, stores like Bloomingdales, Saks 5th Ave and Nieman Marcus prove to be alive in the holiday spirit.
Perpendicular to Mich Ave is Oak St. which houses more designer stores, among nicer brands such as Barbour, AllSaints, and Madewell. The area serves as a bit of an escape from the crowds of Michigan since it’s a little less grand and a little more quaint. I recommend walking in and out of the surrounding streets to explore more of what’s around off of the high street.
It is easy to make a day out of the Chicago Institute of Art and Millennial Park since they are right next to each other and I would 10/10 recommend doing so! I was surprised at how vast the collections were at the art museum. They literally have every sort of art imaginable, all wonderfully curated and displayed with countless masterpieces from artists of every time period. Besides the more famous American art and impressionists collections that everyone goes to see, the museum has a super cool gallery of European armor from as early as the 7th century. I can be a bit of a history nerd, so I found the display extremely interesting and well done. They also have an exhibit of miniature rooms, like doll houses, that show scenes from different time periods and locations.
Down the street from the museum is the classic instagram famous mirrored sculpture otherwise known as the Bean. I really wanted to check out the bean for the soul reason of getting a picture, but I ended up being more fascinated in it than I thought I would be. Yes, it is touristy and crowed, but that is all apart of the fun and allure. The shape of the sculpture creates many different illusions with the bean-shaped mirror that changes at every angle and location. You can move anywhere around and you’ll get a totally different shot. It also reflects a beautiful and well-positioned image of Chicago’s sky line, making it a delight for both tourists and locals alike (and of course insta-worthy!).
Like any major metropolis, Chicago has a wide range of cuisine and food specialities. I’m honestly not a big deep dish fan (prefer NY pizza for sure, sorry Chicago), so I opted for other indulgences such as donuts. Stan’s Donuts is a serious must try. They are located right on busy Michigan Avenue, but have 8 other locations throughout the city with their cute little cafe-like shops also serving coffee and gelato. I tried the nutella banana filled donut and the blueberry cream cheese pocket donut which were both amazing. Honestly though, all of Stan’s array of classic and unconventional donuts looked fabulous (I’m that person that would try everything); I doubt you can go wrong.
I checked out Eataly Chicago which was the first time that I’d gone to an Eataly. Eataly is a food concept department-like store that specializes in imported authentic Italian food with the idea that food is a celebration and an essential part of culture. The first stores started in Italy and they are now in many major cities around the world with Chicago being one of four in the US. The indoor market has different stations serving up Italian specialities such as gelato and made-to-order cannolis. There are different casual restaurants and many bars that allow you to “bar-hop” throughout Italy.
For a fun Sunday brunch, Luxbar in the gold coast neighborhood is classic and fun with signature entrées and delicious almond croissants. And for a nice dinner, Brindille proves to be a fantastic dining experience with decadent and modern french cuisine. Honestly, the highlight of the meal are the amuse-bouch potato beignets which taste like ridiculously good tater-tots. The desert menu is also spectacular with options such as a plate of freshly baked cookies that will make you feel like a little kid on Christmas.
Both the Willis tower and the Hancock tower offer impressive views of the city and a different perspective from above. You have to take a picture at the sky deck on top of the Willis tower. Little clear capsules perturb out of the building making it seem like you are suspended above. It is a little frightening, but super cool to look down (people with a fear of heights: beware).
Walking around the city during the holidays is an experience in itself, but to really get your Christmas fix, head down to Lincoln Park and see the Zoo Lights. Every year from Black Friday to Christmas, the zoo puts up an over the top display of lit up animals and trees, complete with light shows to music. It’s totally free and fun for everyone.