Want to explore Chicago's history and food scene?

Join a 2-hour walking tour where you can try iconic local foods like deep-dish pizza, a Chicago hot dog, and prime steak. As you eat, a guide will share stories about the city's gangster past and mob crime scenes, blending delicious treats with fascinating history.

What We Offer

Get ready to explore Chicago's River North neighborhood, where you'll taste iconic local foods like deep-dish pizza, prime steak, and a Chicago hot dog. As you walk, you'll hear fascinating stories about famous mobsters like Al Capone and uncover their old hideouts, including a hidden tunnel and a former brothel-mansion. You'll also discover historic crime scenes, such as a Cathedral where mob shootings took place, on this unique tour that blends history, food, and thrilling stories.

Highlights

• For One Adult or Child
• Includes three food tastings (enough for a good lunch), soft drinks and water
• Expert local guide with tour of old Al Capone hideouts
• Food and Gangster History in Chicago's River North neighborhood
• Tour Times: Daily at 11:15 AM and 1:30 PM (Please arrive 10-15 minutes early)
• Meeting Point: In front of Hoyt's Restaurant at the Royal Sonesta Hotel (Wacker and Wabash).
• Distance & Duration: The tour is a 1-mile walking tour with four stops. Takes approximately 2 hours.

On this guided tour, a historian will reveal the darker side of Chicago's past. You'll hear true tales of the city's mobster history and how Al Capone built his empire. The journey also explores eerie ghost stories connected to famous landmarks like the Palmer House and the Chicago Theatre. You'll walk through notorious locations such as Death Alley and the Chicago Riverwalk, and finish at the infamously haunted Congress Hotel to learn about the chilling events on its 12th floor.

Highlights

• For One Adult or Child
• Visits inside the Congress Hotel and the Palmer House.
• Guided walking tour with a historian guide.
• Tour Times: Daily at 11 AM, 1 PM, 4 PM, and 8 PM
• Meeting Point: Outside Hoyt's Tavern, next to the Royal Sonesta Hotel.
• Distance & Duration: Approximately 1.5 miles of walking with a 20-minute break. Takes approximately 2 hours.

Hop on a luxury minibus to explore the most historic and notorious neighborhoods of Chicago's Loop and River North. Your guide will immerse you in the city's chilling past with eerie tales from haunted landmarks like the Congress Hotel. You'll also discover gangster lore at places like Holy Name Cathedral, Frank Nitti's secret vault, and an Al Capone speakeasy. The tour includes stops at iconic landmarks such as the Chicago Theater and the Palmer House, providing plenty of photo opportunities.

Highlights

• For One Adult or Child
• Explore the city's history and haunts with an expert guide from the comfort of a luxury minibus.
• One stop at Harry Caray’s Italian Steakhouse
• All taxes and fees included
• Tour Times: Daily at 2 PM, 4 PM, 6 PM and 8 PM
• Meeting Point:The tour begins and ends at the Wabash Street entrance of the Palmer House.
• Duration: The tour lasts approximately 2 hours.

Why You Should Grab The Offer

Step into the shadowy world of 1920s Chicago as you walk through River North, one of the city’s most storied gangster districts. This two-hour guided tour pairs legendary Chicago eats with tales of mobsters, speakeasies, and Prohibition-era crime. You’ll savor local staples like deep-dish and tavern-style pizza, prime steak, and the iconic Chicago hot dog—enough for a full lunch—while exploring notorious landmarks tied to Al Capone and his rivals.

Expect to uncover hidden tunnels once used by bootleggers, visit a mansion-turned-brothel frequented by gangsters, and stop at the site of a historic mob hit outside Holy Name Cathedral. From the culinary icons to the criminal legends, this tour offers a one-of-a-kind blend of flavor and folklore—all led by a passionate, expert guide.