Chicago is a fun, diverse city divided into over 200 distinct neighborhoods. You could spend weeks exploring them as each has something unique to offer. Some of these are known for their ethnicities: There’s Lincoln Square which has a large population of Germans and also Greektown and Chinatown.
Other neighborhoods are known for what you can find or do there. Lincoln Park is known for its zoo and many public beaches, while Andersonville is known for its large LGBTQ+ population and busy urban Clark Street.
Then there is the famous Wicker Park neighborhood where I was lucky enough to call home for a few years. Known for its bohemian vibe, incredible vintage shopping, and hip art galleries, Wicker Park is one neighborhood not to miss on your visit to Chicago. Here I’ll highlight the best things to see and do in this laid-back neighborhood.
1. Shop For Vintage Clothing
I’m not just a budget traveler, I’m also a budget shopper. They kind of go hand in hand — in order to save and budget for travel, I’ve got to budget at home too. For this reason, I love garage sales and thrifting. I also love vintage clothing. One of the best surprises when I moved to Wicker Park was discovering all the incredible vintage shops scattered throughout the neighborhood.
Many of these shops can be found while taking a stroll along the busy street of Milwaukee Avenue. One of my favorite shops is Kokorokoko. It is not only fun to say but has an incredibly spacious layout inside. This store focuses on vintage finds from the ‘80s and ‘90s. Beyond clothing, you can also find retro accessories, books, and housewares.
If you’re looking for vintage older than the ‘80s, check out Vintage Underground. Also located on Milwaukee Avenue, this shop is packed with vintage clothing going back to the ‘50s and ‘60s and through the ‘90s, along with all sorts of jewelry to browse.
Any trip to Wicker Park is not complete without a stroll along Milwaukee Avenue. Stop in and out of the various vintage and boutique shops on a quest to find that perfect retro dress.
2. Myopic Books
Not just any bookstore, a three-level used bookstore packed with over 80,000 books ranging in topics from history, poetry, mythology, music, fiction, and many, many more. Located in the heart of Wicker Park, on, you guessed it, Milwaukee Avenue, it would be easy to spend an entire afternoon at Myopic Books pursuing the hundreds of shelves packed with books on just about any topic you can imagine.
Be sure to check out their weekly schedule. On any given day, there may be a poetry reading, a book signing, or live music. Don’t get there early. Myopic Books is open 7 days a week but not until 12 p.m.; you can browse until 8 p.m.
3. Chicago Bath House
Visit Chicago’s oldest and only traditional bathhouse at the Chicago Bath House in Wicker Park. Operating since 1906 and having gone through major renovations in 2011, when new ownership took over, this bathhouse has kept the old world while entering the new world.
The renovation kept all of the original services, the most popular of which are the traditional “banya” and “schvitz.” These are Russian-style hot rooms similar to saunas. Because these rooms have brick or granite ovens that use gas jets to reach extreme temperatures, the steam that is released is much drier than that of traditional saunas.
The option of three levels of cedar benches allow for dramatically different temperatures to suit your fancy. Within the room are cold water taps. Buckets are used to pour this cold water over your head when the heat gets to be too much. Additionally, there is a cold water pool to plunge into.
Another old tradition that remains in this renovated bathhouse are attendants who are available to give you a plaitza or “rub.” This consists of laying naked on a sheet in the hot room while the attendant uses a handheld birch broom to thoroughly scrub your body with soap. Afterwhich, you are then doused in cold water to get the soap off. If you’re brave enough and up for a little pain with your relaxation, this is for you.
With the new renovation came the addition of a full bar, restaurant, and other salon services such as tanning and scrubs. Come for the hot room and stay for the libations afterward at the oldest bathhouse in Chicago.
4. Get Your Dive Bar Fix
Dive bars are my scene because I love their easy-going, unpretentious feel. It’s easy to become a regular fast. Chicago is famous for dive bars, my most favorite of which is The L & L Tavern located in the Lakeview neighborhood. However, Wicker Park is loaded with them too. Most, as we’re learning, are located along Milwaukee Avenue.
After a morning or afternoon of shopping up and down the avenue, take a well-deserved break at Phyllis’ Musical Inn. It’s been around since 1954 and was Wicker Park’s first musical venue. Locals and visitors alike love its laid-back feel and spacious beer garden. Stop into this saloon and hope you catch some great live music.
If you prefer a rooftop to a beer garden, then Whiskey Business is the place for you. It boasts a 3,000-square-foot rooftop that changes themes with the seasons. Get your ‘80s and ‘90s nostalgia on while sipping on a fruity cocktail. You won’t have to go far, as this one is also on Milwaukee Avenue.
5. Piece
It wouldn’t be an article about things to do in Chicago if I didn’t mention pizza. However, the pizza I’m going to talk about isn’t Chicago-style, surprisingly. It’s New Haven-style (hello memories of one of my favorite movies, Mystic Pizza). At Piece, you can get a variety of the thin-crust, coal-fired Neapolitan pizza along with a cold brew from their seven-barrel brew house.
The pizzas are the main attraction here and I recommend the Hot Doug’s Atomic Sausage pizza that comes with a lovely pepper-filled pork sausage, making this a spicy one. Besides pizza, they have a handful of appetizers and salads on offer.
Pro Tip: If you’re still craving that most famous of Chicago-style pizzas, there is a Lou Malnauti’s in Wicker Park. However, it’s carry-out only. Grab a pizza there and take it to Wicker Park to have a picnic and enjoy the greenery.
6. The Flatiron Arts Building
Along with keeping an eye out to spot the various street art and murals while walking around Wicker Park, you can get a concentration of all things art at The Flatiron Arts Building. (I bet you can guess where it’s located.) Step inside this all-artists studio filled with artists of all kinds and shops to browse. You’ll find all genres of art including visual art, costume design, and filmmaking. There are even some tattoo shops.
It is free to enter and many nights there are events and performances, so be sure to check out the schedule. If you’re lucky enough to be visiting Wicker Park on the first Friday of the month, The Flatiron Arts Building celebrates all things art with a huge party inside. Artists in their studios open their doors and welcome the public.
There is no shortage of things to do in the hip, bohemian neighborhood of Wicker Park. There’s also no shortage of restaurants, dive bars, vintage shops, and art. Pick your fancy and spend a day exploring this walkable neighborhood in Chicago.
