How to Spend an Afternoon in Chicago: A Walk Through Wicker Park

When you visit a big city like Chicago, it’s sometimes hard to find the out-of-the-way spots and neighborhoods away from the main tourist traps of downtown. You might want to wander, but you’re not totally sure which neighborhoods are safe, or where you can find good food or shops that don’t jack up prices for the tourists.

For those of us who want to connect to the communities which we visit, and experience life as a local, we need some help finding ways to do that.

As both a travel writer and a walking tour guide, I’d love to do that for you today by suggesting you take a walk through Wicker Park, a neighborhood in Chicago that I’ve grown to love for its community focus and awesome friendliness. It’s also got some of the top-rated restaurants and boutiques in the city.

Getting There: Damen Blue Line Stop

When you get to Chicago, whether by car, train, or airplane, you’ll find yourself with access to the “L” in nearly any spot in the city. The elevated train runs in colors, so be sure to look for your stop on the right line. There are CTA maps everywhere, but I usually use the Google maps app on my phone – which, by the way, works while you’re going at high speeds underground on the subway.

For Wicker Park, we’re focusing on a single stop: the Damen Blue Line stop. You’ll find this stop is northwest of the Loop/Gold Coast/Near East Side/River North neighborhoods. So, if you’re coming from downtown, you’ll want to hop on going north towards O’Hare.

Google Earth views of the confusing Milwaukee/Damen/North Ave intersection

A Very Brief History of Wicker Park

While you’re riding the train to the neighborhood, I thought a brief history of Wicker Park might help give life to your mini-tour once you arrive.

The neighborhood has been a part of the city since 1837, at just the northwest edge of the city’s lines. Germans and Norwegians were the first groups to settle into the Wicker Park/Bucktown area. Later, other groups flooded in, and changed the face of the neighborhood again, bringing in a mix of both Jewish and Polish culture.

Beer Baron Row – or Hoyne between Schiller and Pierce – is one of the streets in this neighborhood that’s decked out in mansions from the days before Capone and prohibition. These mansions were built by the wealthiest brewery owners of the time.

The neighborhood still has many of the oldest buildings still in place and has turned them into newer offerings, such as the Noel State Bank built in 1903 now converted into a Walgreens – complete with a “Vitamin Vault.”

Let’s Get Walking

Once you arrive at the Damen Blue line stop, exit and turn toward the funky multi-directional intersection.

I’ll give you a hint right off the top of the tour – anytime you come to an intersection like this, the name of the street on the top of the posted sign is the first street on the right.

In this case, the first (sharp) right is Milwaukee Avenue, and the second right (perpendicular to Damen) is North Avenue.

Grab a Coffee

There is a plethora of coffee shops in Wicker Park and Bucktown. My two personal favorites are Stan’s Donuts – they have awesome donuts, including three gluten-less flavors – and the Wormhole. You can find Stan’s just outside the Damen stop and the Wormhole is down Milwaukee a couple of blocks.

The Peanut Butter Pocket from Stan’s Donuts

Snag Some Awesome Threads

Wicker Park is loaded with awesome clothing shops. There are contemporary boutiques with current designers, but since I’m a thrift nut, I lean towards shopping in the vintage shops. You can find a combination of both at Una Mae’s, or just some vintage items at Vintage Underground.

Peruse Some Records and Books

Inside Reckless Records

Since I’m also a lover of media, and I know heaps of you are, too, I can’t help but mention my two favorite bookstores and another awesome Chicago gem. Reckless Records has thousands of titles in vinyl, DVDs, CDs and other media, while Myopic Books and Volumes Book Café offer some of the best choices in new and used books anywhere in the city. Volumes specifically works with local authors, as well.

Volumes Book Cafe Interior 1 09 2019.jpg
Entering Volumes Book Café

Dine at Some of Chicago’s Best Restaurants

Whether you’re looking for some Michelin-star restaurants like Schwa or Bib Gourmand Award winners like Antique Taco, or just a good nibble at a low-key joint like the Chicago classic Jay’s Beef, Wicker Park is loaded with the best eats in practically any category.

Inside Antique Taco

Experience a Tea Ceremony

If you’re a tea fanatic like me, you’ll want to get to the Easthill Tea on Milwaukee Avenue. Keqi Meng, a Chinese born tea expert, has brought a beautiful shop into the Bucktown neighborhood. Here he serves tea and celebrates tea ceremonies with his clientele, teaching us the importance of family and connectedness through tea.

One of the tea pots at Easthill Tea Co.

Sniff Some Blooms

My final thought for a quick tour through Wicker Park is the beautiful Asrai Garden shop where you can sniff some flowers, pick up some unique jewelry, or purchase some distinct gifts for family members. I love walking into this shop and smelling the beautiful scents and scanning the flowers to create my own beautiful bouquet.

A few of the gift choices at Asrai Garden

Final Thoughts on Wicker Park and Bucktown

There are loads more shops, restaurants and things to do in Wicker Park in any kind of weather. If it’s a comfortable day, walk the 606 Trail – officially the Bloomingdale Trail – hang out in Wicker Park. If it’s a little cooler – or a lot colder like this winter has been – get warm while looking through some art galleries, like the Jackson Junge, or grabbing a book for a reading session at the aforementioned Volumes Book Café where you can grab a cocoa or coffee, too.

Some street art to enjoy from many angles at the 606

If you’re interested in a more in-depth look at this neighborhood, I’ve created a 1-Day itinerary with Unanchor Travel. The guide will be released soon.


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