Imagine strolling through Chicago’s historic streets, tasting legendary deep-dish pizza, savoring a classic Chicago hot dog, and hearing gripping tales of Al Capone and the gangsters who once ruled the city’s underworld. For just $81 per person, this 2-hour walking tour takes you through the bustling River North neighborhood, blending history, culture, and cuisine in a way that’s as engaging as it is delicious. Led by guides whose passion and storytelling ability shine, you’ll visit spots that once served as gangster hideouts, underground tunnels, and even a mansion linked to illicit activities.

What we love most about this tour is how it balances authentic food experiences with fascinating mafia history. You’ll get to taste some of Chicago’s most iconic dishes, like deep-dish pizza and a Chicago-style hot dog, while learning about the city’s notorious gangsters. Plus, the chance to explore hidden tunnels and historic buildings makes this more than just a food tour—it’s a mini adventure into Chicago’s wild Prohibition era.

One potential consideration is the walking distance involved—around a mile across four stops—so comfortable shoes are a must. Also, while the tour includes enough food to serve as a hearty lunch, it’s mostly a daytime activity, so it might not be ideal if you’re looking for a late-night experience.

This tour is perfect for those curious about Chicago’s gangster past, lovers of classic American foods, and anyone wanting a lively, story-rich experience that combines history with flavors. If you enjoy engaging guides and memorable stories, you’ll find this tour a real highlight of your trip.

This experience made our article of What Are The Best Walking Tours In Chicago? Our Top 16 Picks.

Key Points

Historic neighborhoods: Walk through Chicago’s fascinating River North area, rich with gangster lore.
Tasty highlights: Sample deep-dish pizza, tavern-style pizza, prime steak, and the famous Chicago hot dog.
Hidden history: Visit old gangster hideouts, underground tunnels, and locations linked to Capone’s era.
Expert guides: Guides are praised for their knowledge, storytelling, and friendly manner.
Authentic experience: The food tastings are substantial, often enough for a satisfying lunch.
Accessible & flexible: The tour is wheelchair accessible, with options to cancel or reschedule as needed.

You can check availability for your dates here:

A Deep Dive into the Experience

Chicago’s reputation as a city of gangsters and great food is well-earned. This tour offers an engaging way to explore both facets in a compact package. Starting out in front of Hoyt’s Restaurant at the Royal Sonesta Hotel, your guide—such as Talia, Baylor, Alan, or Trevor—welcomes you with enthusiasm. From there, the walk begins, and you’ll quickly realize that this isn’t just about eating; it’s about storytelling, locating, and understanding the city’s past.

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Day of the Tour: What to Expect

The tour covers roughly one mile of walking, with four main stops, each packed with historical significance and tasty bites. The pace is gentle, allowing plenty of time to listen, ask questions, and savor each dish. The food tastings, which include Chicago’s signature hot dog, deep-dish pizza, and prime steak, are more than just samples—they’re mini meals that leave you full and satisfied.

The Historic Stops

One of the most exciting aspects is visiting an underground tunnel used by Prohibition gangsters. These tunnels, often hidden beneath restaurants, reveal Chicago’s secretive past when illegal activities thrived in shadowy alleyways. Another highlight is a mansion once used as a gangster brothel, giving a glimpse into the lavish lifestyles of the underworld elite.

You’ll also see where gangsters relaxed, made deals, or perhaps met a violent end—like the cathedral where Capone’s men were gunned down. These sites aren’t just remnants of the past; they’re stories etched into the very streets you walk.

Food and Stories: A Perfect Pairing

Throughout the tour, guides share ** riveting tales** of Al Capone, the North Side Gang, and the chaos of Prohibition. The stories are detailed, often humorous, and delivered with a passion that makes history come alive. Many reviews commend guides like Baylor, Alan, and Talia for their knowledge, friendliness, and storytelling skills.

Participants frequently mention how the food elevates the experience—deep-dish pizza is a must-try, with some reviewers noting they went back later for another slice! The hot dog with sport pepper garners special praise, with one reviewer claiming it was “so good” that they ate another later that day.

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Practical Details

This tour is designed for easy accessibility and flexibility. It’s wheelchair accessible, and with options to cancel up to 24 hours in advance or reserve now and pay later, it’s a low-risk choice. The 2-hour duration makes it ideal for a midday activity, fitting well into most itineraries.

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Value for Money

At $81, the price might seem modest considering the amount of food and inside knowledge you receive. The tastings alone could rival a casual meal, and the historical insights add a rich layer of context that makes this experience more meaningful than a simple restaurant visit.

Why This Tour Works

The combination of delicious food and intriguing mafia stories appeals to a broad range of travelers. History buffs will enjoy reliving Chicago’s gangster era, while food lovers will appreciate sampling iconic local dishes in a lively setting. The guides, many of whom are praised for their enthusiasm and storytelling, help make each stop memorable.

The tour’s pacing and stops are well thought out—enough to keep everyone engaged without feeling rushed. The small group size (not explicitly stated but implied by the reviews) fosters a more personal experience, making it easier to ask questions and soak up the atmosphere.

The Sum Up

If you’re looking for a tour that combines history, culture, and cuisine, this Chicago gangster-themed walk hits all marks. It’s a smart choice for those wanting to get a feel for the city’s colorful past while enjoying delicious local foods. The guides’ storytelling skills and the authentic historic sites make it a worthwhile addition to any Chicago itinerary.

Perfect for history enthusiasts, foodies, and adventure seekers who enjoy a good story paired with great eats, this tour offers a lively, engaging way to experience Chicago’s most notorious era.

FAQ

Is this tour suitable for all ages?
Yes, the tour is appropriate for most ages since it’s a walking experience with food tastings. Young children may enjoy the stories, but be aware that some sites involve walking and standing.

How much walking is involved?
The tour covers about one mile across four stops. It’s leisurely, but comfortable shoes are recommended because of the walking and standing.

What food is included?
You’ll taste two kinds of pizza (deep-dish and tavern-style), prime steak, and a Chicago hot dog. These are substantial enough to serve as a lunch.

Are alcoholic drinks included?
No, alcohol is not included in the tour price.

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

Is the tour accessible for wheelchair users?
Yes, the tour is wheelchair accessible.

What should I bring?
Bring comfortable shoes and perhaps a water bottle, especially if the weather is warm or rainy.

What is the best time of day to take this tour?
The tour is typically available in the morning or afternoon, fitting nicely into most travel plans.

Whether you want to satisfy your curiosity about Chicago’s gangster history or just enjoy some classic American fare in a lively atmosphere, this tour promises a blend of both that’s hard to beat.