Chicago: Gangsters and Food Tasting Walking Tour

Chicago: Gangsters and Food Tasting Walking Tour Review

If you’re visiting Chicago and have a taste for history, crime stories, and delicious bites, this Gangsters and Food Tasting Walking Tour offers a compelling mix of both. For just $81, about two hours of walking through the city’s historic River North neighborhood, you’ll get a hefty dose of local cuisine paired with tales of Chicago’s notorious gangsters—think Capone and his rivals. The glowing reviews, with an impressive 4.6 out of 5 from 157 travelers, suggest this tour hits the mark for many visitors.

What really sets this experience apart is the way it seamlessly combines culinary delights—such as deep dish pizza, prime steak, and a Chicago hot dog—with fascinating gangster stories and hidden historic sites. It’s perfect for history buffs, food lovers, or anyone curious about the city’s darker past. One of our favorite aspects? The authentic storytelling from guides like Alan, who’s lauded for his humor, knowledge, and engaging style.

A possible consideration is the walking component—the tour covers about a mile and involves standing at four stops, so comfortable shoes are a must. Also, since the tasting food amounts to a full lunch, it’s best suited for those ready to eat and explore at a leisurely pace. If you’re after a relaxed, informative, and flavorful experience that offers a taste of Chicago’s past and present, this tour is a solid pick.

Key Points

• Authentic Food Tastings: Sample Chicago classics like deep dish pizza, hot dogs, and prime steak.
• Historical Insights: Learn about Chicago’s gangster era through stories of Capone, underground tunnels, and historic sites.
• Expert Guides: Guides like Alan and Baylor are praised for their knowledge, humor, and storytelling.
• Hidden Locations: Visit old gangster hideouts, underground tunnels, and spots where famous gangsters relaxed or met their fate.
• Value for Money: The tour includes multiple tastings (equivalent to a full meal), access to historic sites, and engaging storytelling—at a reasonable price.
• Accessibility: The tour is wheelchair accessible and departs rain or shine, making it flexible for different travelers.

In-Depth Look at the Experience

The Itinerary and Stops

The tour kicks off outside Hoyt’s Restaurant at the Royal Sonesta Hotel, located right on the Chicago River. From here, you’ll embark on a two-hour walk through the city’s River North neighborhood, a historic area once dominated by gangsters and speakeasies.

One of the first stops takes you into an old basement where gangsters once used tunnels for secret meetings or escapes. This underground tunnel is a real highlight, offering a glimpse into the clandestine practices of Prohibition-era criminals. It’s a tangible connection to the past, and guides often share stories of how Capone’s crew and rivals operated behind the scenes.

Next, you’ll visit a vintage mansion that once served as a gangster’s hideout or perhaps a brothel—these locations are ripe with stories of illicit activity and social intrigue. The tour also includes a stop at a historic cathedral, where, according to local lore, gangsters met their end or did deals that shaped Chicago’s underworld. The guide’s storytelling here makes this place come alive, with tales of violence, betrayal, and power plays.

Food Tastings and Why They Matter

The food stops are thoughtfully chosen to showcase Chicago’s iconic cuisine. You’ll indulge in two types of pizza—a classic deep dish and a tavern-style slice—giving you a taste of local flavor that’s hard to beat. Reviewers mention that these slices are hearty, often enough to substitute for lunch.

A stop at a renowned steakhouse provides an opportunity to enjoy prime beef, prepared to your liking, echoing Chicago’s reputation for excellent steak. The hot dog, another staple, is served with typical garnishes—though some reviewers noted the hot dog portion was smaller than expected, it still offered the authentic Chicago experience.

The tastings are generously portioned, making the tour feel more like a food crawl or a casual lunch rather than just a snack. This approach makes the experience especially good value, as you leave with your appetite satisfied and your knowledge deepened.

The Guide and Atmosphere

Reviews consistently praise the guides—such as Alan, Baylor, Talia, and Avery—for their wealth of knowledge, engaging storytelling, and sense of humor. One reviewer mentioned that Alan’s passion for Chicago’s gangster history made the tour memorable, blending facts with amusing anecdotes. Baylor’s enthusiasm and friendliness also received high marks, making the experience feel personal and fun.

The tour maintains a lively yet respectful tone, balancing entertainment with education. Guides also point out great photo spots and little-known facts, adding layers of interest beyond the main stories.

Group Size and Pacing

Most reviews describe the group size as manageable, around 10-15 people, which creates an intimate atmosphere conducive to questions and interaction. The pacing is relaxed, with enough time at each stop for photos and exploration. Since the walk is about a mile total, comfortable shoes are essential.

Accessibility and Practicalities

The tour departs rain or shine, so good weather gear is advised. It’s wheelchair accessible, which broadens its appeal. Starting at Wacker and Wabash Wacker Streets makes it easy to find, and the tour ends back at the same meeting point, simplifying logistics.

The Value Proposition

While $81 per person might seem steep for a two-hour walk, the inclusion of three substantial food tastings elevates this experience from a typical city tour to a delightful culinary adventure. Reviewers noted that the food alone could serve as a full lunch, meaning you’re not just paying for stories but also for a hearty meal.

The access to historic sites, underground tunnels, and behind-the-scenes stories enhances the value, especially given the lively, knowledgeable guides. Many guests mention that the experience is well organized, with clear communication and a good balance of history and humor.

Who Will Love This Tour?

This experience is ideal for history enthusiasts, especially those curious about Chicago’s gangster past. Food lovers will appreciate the authentic Chicago eats, and anyone seeking a fun, engaging way to learn about the city’s culture will enjoy the storytelling. It’s also suited for first-time visitors wanting a quick, rundown of the city’s criminal and culinary history.

It’s perfect for groups, couples, or solo travelers who enjoy walking and exploring, with the added bonus of delicious bites and captivating stories. Since the tour is wheelchair accessible and departs rain or shine, it accommodates a range of mobility and weather preferences.

Final Thoughts

In short, the Chicago Gangsters and Food Tasting Walking Tour offers a lively, authentic glimpse into a colorful part of Chicago’s history. The combination of delicious local foods, hidden historic sites, and entertaining storytelling makes it a memorable experience that appeals to many travelers. The guides’ passion and knowledge truly shine, elevating the tour from a simple food walk to an engaging journey through Chicago’s past.

If you love stories of crime and glitz, crave hearty Chicago staples, or want to see a different side of the city, this tour is well worth considering. It balances value, entertainment, and education, making your time in Chicago even more memorable.

FAQ

Is this tour suitable for all weather conditions?
Yes, the tour departs rain or shine, so it’s best to dress appropriately for the weather. Good shoes are recommended since you’ll be walking about a mile.

How long is the walking portion?
The tour covers roughly one mile, with four stops. It’s designed to be a relaxed pace, allowing plenty of time for photos and exploration.

What is included in the price?
You get three food tastings, which are enough to serve as a full meal, plus water and soft drinks. You also gain access to old gangster hideouts and historic sites with a knowledgeable guide.

Are alcoholic drinks included?
No, alcohol is not included, but the tour does not prohibit bringing your own if desired.

Is the tour accessible for people with mobility issues?
Yes, the tour is wheelchair accessible, making it suitable for travelers with different mobility needs.

Can I cancel or reschedule?
Yes, you can cancel up to 24 hours in advance for a full refund. You can also reserve your spot now and pay later, offering flexibility for your travel plans.