Chicago: Gangsters and Food Tasting Walking Tour

If you’re heading to Chicago and love a good mix of history, food, and city vibes, this tour might just be worth your time. It promises to combine delicious iconic bites—think Chicago deep-dish pizza, hot dogs, and juicy steak—with stories of famous gangsters from the Prohibition era. The idea of walking through a neighborhood steeped in gangster lore while sampling some of Chicago’s best foods sounds pretty compelling, doesn’t it?

What really catches our eye about this experience is the way it balances entertaining storytelling with tasty, filling food stops—and all within just two hours. Plus, the access to old gangster hideouts, including underground tunnels used by Al Capone, adds a dash of adventure and mystery. The reviews highlight guides who are knowledgeable and fun, making it clear that this isn’t just a food crawl but an engaging journey back in time.

That said, it’s worth mentioning that this tour is mostly about walking and tasting, so if you’re not into more active outings or have mobility concerns, it might require some extra planning. Also, while the food is plentiful and satisfying, it’s a good idea to come hungry—these tastings add up to a solid lunch.

This tour is best suited for food lovers, history buffs, and those intrigued by Chicago’s gangster past. If you’re after a relaxed, friendly way to explore the city’s stories and flavors in a manageable time frame, this might be just the ticket.

Key Points

• Balanced Experience: Combines food tastings with gangster history, making it engaging on multiple levels.
• Duration & Pace: It’s a 2-hour walk covering approximately 1 mile with four stops, so it’s easy to follow and not overly strenuous.
• Food Quality & Variety: Enjoy two types of pizza, hot dogs, and prime steak—stories and flavors that offer a true taste of Chicago.
• Expert Guides: Many reviews praise guides like Baylor, Alan, and Talia for their knowledge and enthusiasm.
• Historic Access: Includes visits to underground tunnels and old gangster hideouts, adding a sense of adventure.
• Value for Money: For $81, you’re getting a well-rounded experience with multiple tastings, stories, and access to historic sites.

You can check availability for your dates here:

What’s Included and What to Expect

This two-hour walking adventure is set to take you through the streets of River North, a neighborhood once buzzing with the illicit dealings of Chicago’s most notorious figures. The tour meets outside Hoyt’s Restaurant at the Royal Sonesta Hotel—an accessible, central starting point—and heads out rain or shine. Comfortable shoes are advised since you’ll be walking roughly a mile with four key stops.

Included in the price are three food tastings—which are substantial enough to serve as a lunch—plus water and soft drinks to stay hydrated during the walk. Your guide, an expert local, will narrate stories about Chicago’s gangster past, point out historic sites, and lead you into old hideouts, including a famed underground tunnel once used by Capone himself.

Knowing the tour length and pace is helpful: it’s designed for a relaxed stroll, not a marathon, with just a mile of walking between four stops. The experience is suitable for most, and the tour is wheelchair accessible, making it convenient for a wide range of travelers.

The Itinerary: What You’ll See and Taste

Starting Point and First Stop: Food & Gangster Lore

As you gather in front of Hoyt’s Restaurant, the guide kicks off the tour with an overview of Chicago’s gangster era. Expect stories about notorious figures like Al Capone and the North Side Gang, intertwined with local history. The first tastings typically include a Chicago hot dog—famous for its unique toppings—and a little background on the city’s most beloved street food.

Underground Tunnel and Historic Hideouts

One of the most talked-about features is a visit to a basement tunnel used by gangsters during Prohibition. This underground pathway adds a dash of intrigue and a tangible connection to Chicago’s criminal past. Previous guests have enjoyed seeing hidden parts of the city that most travelers miss, and many reviews highlight how fascinating and well-presented these stories are.

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A Mansion Turned Brothel and a Daring Gunning

Next, you might visit a mansion that served as a gangster-run brothel, or see the site of a notorious shooting at the local cathedral where Capone’s men were involved. These locations are chosen for their historical significance and vivid stories, giving you a sense of the dangerous, glamorous, and sometimes deadly world these gangsters inhabited.

Final Stop: Harry Caray’s and the Deep Dish Pizza

The tour usually concludes at Harry Caray’s restaurant—owned by the man who helped take down parts of Chicago’s mafia in the early 2000s. Here, you get to sample Chicago’s iconic deep-dish pizza along with prime steak, rounding out the experience with a hearty, satisfying taste of the city’s culinary traditions.

Guides and Their Stories

A common thread in reviews is how engaging and knowledgeable the guides are. Whether it’s Baylor, Alan, Talia, or Trevor, guests consistently mention guides who are passionate storytellers. They don’t just recite facts—they weave histories, personal anecdotes, and humor into their narratives, making the stories of gangsters like Capone come alive.

One reviewer noted, “Alan was friendly, patient, and knew the city’s history inside and out,” while another highlighted Baylor’s energy and storytelling skills. This level of enthusiasm makes the experience more than just a food tasting; it becomes a mini history lesson wrapped in fun.

The Food: More Than Just Snacks

What sets this tour apart is the quality and variety of the food. Multiple reviews mention how the tastings are substantial—adding up to a full meal—so coming hungry is a good idea. You’ll enjoy a classic Chicago hot dog, two types of pizza (deep dish and historic tavern-style), and prime steak with fries.

Guests often rave about the fabulous flavors. One reviewer even said, “I went back that night for a steak dinner because I couldn’t stop thinking about the food.” It’s clear that the culinary stops are memorable and well-curated.

The Value: Is It Worth the Price?

For $81, you’re getting a solid blend of history, culture, and hearty food. The reviews suggest the experience is quite good value—especially given the number of sites visited, the access to hidden tunnels, and the quality of the tastings. Many guests feel it’s a satisfying way to spend a couple of hours, filling both mind and stomach.

Practical Tips

• Arrive early at the meeting point outside Hoyt’s Restaurant.
• Wear comfortable shoes as you’ll be walking and standing.
• The tour is rain or shine, so dress accordingly.
• Since the tastings are filling, plan for the rest of your day accordingly.
• If you’re a history enthusiast or foodie, you’ll find plenty to love here.
• Remember, alcoholic drinks are not included, but you might find some establishments offer options if you wish.

Who Will Love This Tour?

This experience is perfect for those who enjoy a relaxed pace, good storytelling, and hearty food. History buffs interested in Chicago’s notorious past will find plenty of engaging tales, while food lovers will appreciate the carefully chosen tastings. It’s also a great way to explore a neighborhood with a storied past without the fuss of a longer, more vigorous tour.

Final Thoughts

In the end, the Chicago Gangsters and Food Tasting Walking Tour offers a satisfying blend of history, food, and local color. With attentive guides, tasty bites, and access to hidden sites, it’s a fun, informative activity that provides a different perspective on the city. If you’re curious about Chicago’s gangster era and want to taste some true Chicago classics, this tour is worth considering.

Is this tour suitable for children?
While not specifically marketed as a family tour, children interested in history and food might enjoy it. The tour involves walking and some storytelling that can appeal to older kids and teenagers.

How long is the walking part of the tour?
The tour covers about one mile of walking between four stops, so it’s quite manageable for most people.

Are drinks like alcohol included?
No, alcoholic beverages are not included. The tour includes water and soft drinks.

What should I bring?
Comfortable shoes are recommended since you’ll be walking around the neighborhood.

What kind of foods will I taste?
You’ll sample two types of pizza (deep dish and tavern-style), a Chicago hot dog, and prime steak. These tastings are enough to feel like a full lunch.

Does the tour go rain or shine?
Yes, it departs rain or shine, so dress accordingly.

Is the guide knowledgeable?
Absolutely. Multiple reviews praise guides like Baylor, Alan, Talia, and Trevor for their storytelling skills and passion for Chicago’s history.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund.

If you want a relaxed, tasty, and story-rich way to get to know Chicago’s past and present, this tour could be just what you’re looking for. It’s a mix of history, culture, and comfort that will leave you full of good stories and good food.

You can check availability for your dates here: