After we booked our Airbnb in Chicago’s Wicker Park neighborhood, I worried I’d made a terrible mistake. The area was quite far away from any major tourist spots and definitely not walkable to the restaurants I had hoped to visit in West Loop. I’d read that Wicker Park would be a great alternative outside the city center, but now all I could see was the amount of added travel time it would create to get there.
Part of the reason I leaned towards Wicker Park, though, was because of Chicago Food Planet’s Food & Cultural Walking Tour. They have a couple neighborhoods they currently offer tours for (Lincoln Park, Chinatown, Gold Coast), but I became intrigued by the Bucktown/Wicker Park tour last year when I started thinking about a Chicago trip. What better way to learn about the neighborhood than through food?
Turns out, I think we made the right move! Granted, next time I’d probably prefer to stay in Bucktown over Wicker Park, since it’s a little cleaner and more family-friendly. But all-in-all, the neighborhood was very our style. Quiet, local, and unique.
We set out on a dreary Thursday morning on our way to meet the tour group at George’s Hot Dogs in Bucktown, the first stop on the tour. Our guide Jade introduced herself and offered to let us take a seat inside while we waited, since it was starting to rain. We warned her that we might only stay on the tour as long as Evelyn would allow and not to be alarmed if we suddenly disappeared. I had gone into the whole thing with the notion that I’d be totally ok with leaving if necessary, which helped ease (some of) my anxiety about taking a 1 year old on a 3 hour walking tour. We settled down in the back of George’s and Evelyn immediately became antsy (mostly because it was almost lunch time). “Oh gosh,” I thought. “How is this going to work??”
Jade brought out our first tasting, a quintessential Chicago-style hot dog, which we quickly cut it into pieces to feed our hungry little monster. The Chicago dogs were topped with 7 signature ingredients: onion, tomato, sweet relish, peppers, celery salt, mustard, and one hefty pickle spear, all on a poppy seed bun. For the time being, Evelyn seemed satisfied.
We carried on down Damen Avenue until we reached The 606 (or Bloomingdale Trail), an old elevated train line that has since been converted into a 2.7 mile walking path akin to New York’s Highline. The renovated trail and green space officially opened in June 2015 and is in stark contrast to the neighborhood of yesteryear.
Today the streets are lined with trendy eateries and loft apartments, but it wasn’t always so. The area was originally settled by Polish and German immigrants. It gets the name Bucktown from the many goats (male goat=buck) that were once raised here by its blue collar residents.
The next stop on our tour was just past the 606 at Mindy’s Hot Chocolate. It was a quick stop for an iced hot chocolate topped with a housemade marshmallow; the perfect treat for a summer day. Hot Chocolate serves a full lunch and dinner menu as well, and is a local favorite, with Mindy Segal being a James Beard Award-winning chef.
From there it was just a few blocks south to Goddess and Grocer for a lighter eat. Jade served up a beloved kale salad, one of their bestsellers. Their trick is to blanch the kale first to take out some of the bitterness out of the leafy green. And it works! It was a surprise favorite among the group.
Goddess and Grocer doesn’t have a ton of seating room, but is perfect for a grab and go lunch. Families can pick their own favorites and head down to Churchill Park (just past the 606) for a picnic. And don’t forget dessert (maybe a slice of their beautiful rainbow cake?) while you’re at it!
As for us, we kept on our way and crossed over North Avenue, which divides the two neighborhoods (Bucktown to the north and Wicker Park to the south). The difference among the two can be seen almost instantaneously. “Like Bucktown, but a little rougher around the edges,” was Jade’s spot-on description on Wicker Park. We stopped into Piece Brewery and Pizzeria on North Avenue for a slice.
Piece has made it’s home in what used to be an old truck garage, and we settled into one of the old receiving spaces that now serves as a sunken dining area. While Chicago might be famous for deep dish pizza, it’s Piece’s thin crust New-Haven style pizza that is a hit here. The micropub also brews their own beer on site, and since they don’t distribute it, it can only be enjoyed in house. We noshed on a white pizza topped with tomato and basil alongside a small tasting of their Golden Arm brew, a German-style kolsch beer.
The group was thoroughly stuffed after adding a slice of pizza to our already full stomachs, but this was no time for slowing down. We veered off the main drag into a more residential neighborhood, strolling past brick townhouses with their black wrought iron fences.
Well, except for that one.
Cutting across Milwaukee Avenue, we found ourselves in the Wicker Park. With children running across the field and dogs playing in the dog park, we looped around the south side of the park to see some of the historic homes that lined Schiller Street.
In the early 20th century, the neighborhood was a mix of residents from all sorts of backgrounds and economic classes, many of them moving out to the “suburbs” after the Great Chicago Fire. They rebuilt their homes in beautiful (and sturdier) brick. But in the mid-1900’s, many of these wealthier residents left for the Gold Coast and other more desirable neighborhoods, leaving Wicker Park’s beautiful mansions behind. A good majority of them fell into disrepair over the next 30 years. Starting in the 1980’s, an influx of young professionals saw the value in buying up these mansions and restoring them back to their original condition. But because of the area’s Chicago Landmark District status, regulations for renovation create additional hurdles, and the transformation (particularly around Wicker Park) has been slow and costly.
Back outside the park, Evelyn was waking from her stroller nap as we continued through the neighborhood. We stopped at the Victorian home on Hoyne Avenue that used to be the local American Legion post. Outside on the front lawn still sits a real World War I-era cannon, said to have protected Chicago’s Navy Pier at one time.
Back on the road to food, we made our next stop at Sultan’s Market for a falafel pita. The owner, Jordanian emigrant May Ramli, opened the restaurant in 2001. She originally served American foods she thought her customers might like: hot dogs, meatball sandwiches. But one day she brought in a batch of hummus and it sold out in a day. The neighborhood hipsters had never had anything quite like it! From then on, May transformed her kitchen, and now serves up the food she grew up on: everything from tabbouleh salad to lamb schawarma, and of course, that famous falafel.
Almost 3 hours after the start of our tour we made it to the last stop just outside the blue line station: Stan’s Donuts. Because after 5 well-portioned dishes, there’s always room for a giant glazed donut, right?
Stan’s is actually a California-based donut shop, but that doesn’t mean it’s not a favorite here as well. It was brought to Chicago when Rich Labriola, owner of the local Labriola Baking Company, saw Stan on a TV travel show and felt inspired to strike up a partnership to bring the West Coast donuts to the Midwest. We admittedly had to take ours to go, or we weren’t going to make the walk back home. But Stan’s does have quite the selection, and I’d love to come back for an apple fritter someday! Plus, it’s open late, so it’s the perfect after-dinner treat.
After stuffing our faces for 3 hours, it was time to head back home. Evelyn’s cat nap gave her a burst of new energy and she wasn’t interested in sitting any longer!
We enjoyed our time with Jade and Chicago Food Planet a ton, and doing it with a baby really wasn’t too bad at all! If you’ll be staying in one of the neighborhoods they offer tours in, I’d highly recommend it for a fun and different experience.
Yes, after all that, I’m feeling confident we made the right decision to stay in Wicker Park. Heck, I think we might even be back sooner than later for more donuts and kale salad.