Custom Chicago Walking Tours

I enjoyed how the tour was catered to our interest. Not only did we eat food that is known for the area but also the history and architecture around the food industry.

My daughter, her friend, and I spent an unforgettable afternoon with Henry from Portal Tours in Wicker Park, and it was the highlight of our Chicago visit.
 We met Henry at the Gurgoyle Fountain. The original had been taken out in 1908 replaced with a plain jet spray, but they recreated it to its original design under the 2nd Mayor Dailey in 2002.

 We then made our way to Hoyne Avenue’s Beer Baron Row—a showcase of grand mansions built by German brewing magnates in the late 19th century. Henry stopped at several of these homes, weaving stories of the families, architecture, and immigrant history that gave the neighborhood its character. Walking those shaded blocks felt like stepping into another era. From there, we crossed near the Bloomingdale Trail (The 606), Chicago’s remarkable elevated greenway. Henry explained its history as a former train line, now a nearly three-mile park, with talk of possible extensions all the way to the lakefront.
 Our first tavern stop was an architectural gem: a Schlitz Brewery tied-house, complete with the brewery’s iconic “belted globe” insignia, restored in bright color. A plaque on the building commemorates it as a Chicago landmark. Hearing Henry describe how tied-houses worked, and how prohibition policies backfired by making beer cheaper, made me see the building with fresh eyes.
 Our walk eventually brought us to The Map Room, a bar I hadn’t stepped into since my Chicago days. Opened in 1992 as a “traveler’s tavern,” its walls lined with maps and vintage guides, it still feels like a home for wayfarers and neighbors alike. Here Henry introduced us to the legendary “Chicago Handshake”: a shot of Malört with an Old Style chaser. I didn’t find Malört as terrible as its reputation suggests. Maybe my palate is already trained on Fernet, but that lingering aftertaste was something else. The fact that Malört has a place on The Map Room’s shelf feels fitting: this is a bar where tradition and the unexpected meet, inviting you to try something both bitter and legendary. We later passed another tied-house, this one shuttered and painted completely white, its Schlitz emblem erased—a stark contrast to the brightly restored landmark we had admired earlier. The afternoon had playful surprises too, like stopping at T-Shirt Deli, Co., a quirky shop styled like a deli counter but selling witty shirts.

 Back at the green space where we began, Henry surprised us with Cohasset Punch—a bold, sweet, winey‑rum concoction. I later learned it was created in Chicago and first bottled in 1899 by Williams & Newman. This ruby-red, fortified‑wine‑like liqueur, served traditionally over a brandy‑soaked peach slice, was once a beloved local cocktail, dubbed “the definitive Chicago cocktail” back in the day. Tasting it was like sipping on a piece of vintage Chicago.
 Henry crafted this tour especially for us, blending architecture, immigrant history, tavern lore, and quirky neighborhood finds. His storytelling is warm and detailed, his knowledge deep, and his passion contagious. If you want to feel Chicago’s history not just through buildings but also through tastes and toasts, take a Portal Tour with Henry.