Custom Chicago Walking Tours

Portal Tours
5.0
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Cancellation Policy
Up to 24 hours before your scheduled admission.
Logan_R
6 days ago
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.

We create custom walking tours for groups of all sizes and interests, blending delicious food experiences with rich historical storytelling. From downtown explorations for high school students, to tavern tours tracing Chicago’s beer history, to local neighborhood food tours, every tour is crafted to be engaging, flavorful, and unforgettable.

Departure Point

  • These are custom tours. We will arrange a meeting point via email.
Return Details
  • These are custom tours. We will arrange a meeting point via email.
Duration1 hour - 3 hoursLanguages Available
  • Human tour guide - English
  • Human tour guide - Spanish

Points of Interest

Stop At: ChicagoChicago, IllinoisBusinesses, architecture, natural landmarks, you name it! We will tailor the perfect custom tour for you. Duration: 2 hours

Additional Information

  • Wheelchair accessible
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Transportation options are wheelchair accessible
  • All areas and surfaces are wheelchair accessible
  • Travelers should have at least a moderate level of physical fitness
Voucher InfoMobile or paper ticket accepted

The tour identified in this promotion is made available through Viator. Groupon is not affiliated with or sponsored by the Portal Tours in connection with this deal. Please contact Groupon customer service for all inquiries related to this offer. Inquiries placed to Viator will be directed back to Groupon. This offer is not eligible for promo codes.

Need To Know Info

For a full refund, cancel at least 24 hours in advance of the start date of the experience.

Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and Savings

Customer Reviews

5.0
based on Groupon 2 reviews
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All Groupon reviews are from people who have redeemed deals with this merchant. Review requests are sent by email to customers who purchased the deal.
Reviewed on
Logan_R
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.
AsadoGuyBuenosAires
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.

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