If you’re visiting Chicago anytime soon, you have more options that you’d possibly be able to do while in town. Figuring out the best places to eat, places to visit, things to see, and places to go can be difficult in a short period of time. Of course, that’s a great problem to have.
But, if that’s your problem, we’d love to help. And one of those ways we’ll help is through suggesting that you don’t limit yourself to the downtown sites that suck tourists in.
Sure, go visit the Shedd Aquarium, shop the Magnificent Mile, and dine at Giordano’s, but go to the neighborhoods, too, and experience more of the real Chicago.
One of the best neighborhoods in Chicago for new-to-towners to visit is Wicker Park. As a Chicago resident and local tour guide, who’s lived and worked all over the city, I’d love to tell you why.
Where is Wicker Park Located?
First off, Wicker Park is an easy train or bus ride from downtown, so it’s easy to get to from practically anywhere you might be staying, even in the suburbs.
There are buses that go to from all over the city, as well as the blue line. Just get off at the Damen blue line stop, and you’ll be in the heart of Wicker Park, in the center of shopping, dining, and near the park itself.
A Brief History of Wicker Park
Image: CC 2.0 by Ben Collins-Sussman via Wikimedia Commons
Secondly, Wicker Park is a fascinating neighborhood that’s packed with rich Chicago history. Even the Walgreens has charm, since it’s a former bank built in 1919. The Walgreens has actually turned the old vault into the Vitamin Vault for a cute, if slightly hokey, little homage to the building’s former life.
In 1868, the Chicago Board of Public Works announced that it wanted to build a park west of Milwaukee and south of North Avenue. The result was Wicker Park itself.
A few years later, in 1871, the Great Chicago Fire, took a significant chunk of the city’s residences, and people began looking for new places to build. This brought development to the Wicker Park area.
During that period, Wicker Park became home to the wealthy northern European immigrants, and the area became known for the large mansions owned by merchants. You’ll still find a number of those mansions along Hoyne and Pierce streets. So many lived here, in fact, that it eventually became known as Beer Baron Row.
Polish immigration into Wicker Park area increased during and after World War II, when it’s estimated that 150,000 Polish folks arrived in Chicago as displaced persons.
Traditionally, immigrants cluster into ethnic enclaves when they immigrate into a new country, and the Polish were no exception as they migrated into Wicker Park and made it their own. Here they built shops, restaurants and banks, and Division Street actually became known as Polish Broadway.
Since that time, Wicker Park has expanded and become a more eclectic neighborhood, but it still boasts fascinating buildings, shops, and other offerings, with more diversity than in the 1940s and 1950s when it seemed to many that everyone in the neighborhood was Polish.
Things to Do in Wicker Park
Because of the rich history of Wicker Park, and the eclectic nature of the many ethnicities that have moved in after the initial collection of Polish folks, the neighborhood has tons of interesting shops, a beautiful park, a large number of restaurants, and a wide variety of artistic and entertainment establishments for anyone to enjoy.
Some of the most interesting places to visit and see in Wicker Park include the following.
1. The 606 – Or Bloomingdale Trail
Nick-named for the zipcode of Chicago, the 606 – or officially Bloomingdale Trail – offers an interesting angle on the city, as you walk above the streets, past parks, and weave your way through a few different neighborhoods in Chicago. If you love walking, and seeing the real sites of a city, then you definitely need to check out this walking trail.
There are multiple access points along the way, meaning you can get to the 606 very easily. Feel free to bring your dog along for a trot or bring up a bike up one of the ramps and traverse the trail on two wheels. Just watch out for foot pedestrians.
If you love parks, you’ll also love the 606, because you can see and access at least six parks from the trail, or close by, including the famous Humboldt Park.
2. The Alliance Bakery
If you don’t love sweets, you can move onto the next list item. If, however, you happen to be like the rest of the universe, you’ll want to check out Alliance Bakery on West Division Street.
Offering cakes, cookies, macarons, cupcakes, pastries, breakfast pastries, and deluxe bars, you will come in hungry and leave completely satisfied.
They also offer a full espresso bar and have Wi-Fi in case you need to sit down and catch up on emails for a bit.
3. Bizaare Bucktown Tours
If you feel like taking a walking tour through the historical parts of the neighborhood, you can book a tour with Bizarre Bucktown Tours, and visit sites like Chicago’s Flat Iron Arts Building – which is supposedly haunted – and learn about various beer barons, artists, mobsters, radicals, and a snake oil tycoon who used to live in the area.
4. Broken Nose Theatre
This unique theater takes a different view of money and the arts. Instead of charging hefty prices, they have the policy of asking their patrons to “pay what you can,” and enjoy the show as you can. This helps to make theater more accessible to everyone. The shows also happen to be fantastic, highly regarded productions.
5. Chopin Theater
Another fantastic theater in Wicker Park is the Chopin. The theater has been around since 1918, and they have a rich history of interesting shows, with a heavy Polish influence beginning in the early years of the company.
Be sure to check out their season and catch a show if one’s playing while you’re in town.
6. Myopic Books
Booklovers, beware. This amazing multi-level bookstore will suck you in and hold you captive for hours, if you’re not careful. You can wander the aisles, which in some senses feel a bit more like a disorganized series of library stacks, or meander down the basement for the sci-fi and fantasy section.
If you’re lucky, you can even catch a poetry reading by local poet Larry Sawyer, who gives his readings in the upstairs space on occasion.
Handlebar is a unique experience with it’s made-from-scratch vegetarian and vegan comfort fare. They serve for all meals, all days a week, and offer a full-service bar and beer garden.
The Subterranean is a unique bar with a live stage upstairs, where rock and hip-hop acts invite their listeners to join the dance party on a nightly basis. For those just wanting a beer, head downstairs to the bar and enjoy the small stage or a quiet room.
There’s a weekly lineup of DJs, and they have one of the most well-attended open mics in Chicago.
9. Emporium Arcade Bar
For something different, check out the Emporium Arcade Bar. Here you’ll find 37 vintage arcade games from the 70s to the 90s, and you only have to pay $0.25 cents to play. There are also 24 different beers on tap, and they focus on Midwest and American craft beers. They’ve also got a large whiskey selection that you’ll want to work your way through.
10. Beer Baron Row
If you love history and are intrigued a bit by the shadier side of the community, you’ll want to walk Hoyne and Pierce Streets in Wicker Park. The beautiful Victorian mansions built between 1868 and 1905 still stand, and many have been restored to their former glory.
11. Margie's Sweets
Another rollicking time for your sweet tooth, Margie’s Sweets has been around 1921, when Peter George Poulos opened the shop not as a candy store, but as an ice cream shop. Later on, Peter’s son married his sweetheart, Margie, and the candy store gained its name.
You can order sundaes, shakes, and tons of other ice cream treats, along with candies, and give your taste buds something to remember.
Simply Put: Wicker Park is Worth a Day While You Visit Chicago
Even if you’re only in Chicago for three or four days, you really ought to check out some of the neighborhoods, rather than focusing your whole time in the Loop. Neighborhoods are where the life of the city takes place, and one of the easiest places to witness Chicago’s uniqueness is in Wicker Park.
Take a walking tour, visit Stan’s Donuts, drink some tea at David’s Tea, or check out any of the places listed above. You’ll have an amazing time and get to know the Windy City just a bit better than the average tourist.