What you'll do:

You'll eat your way through one of Chicago's most storied neighborhoods, pairing iconic local food with the real history of the gangsters who called it home.

• Walk River North like Capone did - Explore the same blocks where Prohibition-era Chicago played out, with a guide who brings the history to life at every stop.

• Taste Chicago's defining foods - Try two styles of pizza (deep dish and tavern-style), prime steak, and a classic Chicago-style hot dog across four stops.

• Go underground, literally - Step into a basement tunnel once used by Prohibition gangsters, hidden beneath one of the tour's dining stops.

• Visit a former gangster brothel - Tour a mansion that served as a private retreat for some of Chicago's most notorious figures during the Capone era.

• Hear the story of the mob's final chapter - Dine at the restaurant owned by the man credited with dismantling what remained of the Chicago mafia in the early 2000s.

This Chicago food tour covers about a mile on foot, with four stops that add up to a solid lunch. It's the kind of afternoon that leaves you knowing the city's history in a way no museum can replicate.

Why we love it for your group:

• Dual-purpose experience - You get a genuine Chicago food tour and a deep-dive history tour in one, so no one in the group has to compromise on what they want to do.

• Hidden locations most visitors never see - The underground tunnel and private mansion stops aren't on any standard tourist map, making this feel like insider access.

• Expert local guide - Your guide handles all the storytelling so you can focus on eating, exploring, and asking the questions you actually want answered.

• Satisfying portions - The four tastings are sized to add up to a full meal, so you won't leave hungry or need to plan dinner right after.

• Rain-or-shine guarantee - The tour runs regardless of weather, so you can lock it into your Chicago itinerary without worrying about rescheduling.

About this experience partner:

Empire Tours Chicago specializes in gangster history tours that go deeper than the typical sightseeing circuit. Known for combining real Chicago food with firsthand stories from the Prohibition era, they've built a reputation among locals and visitors alike for guides who know the history and the neighborhood inside out. Their tours run in River North, one of the neighborhoods most tied to Al Capone's Chicago, and are designed for small groups who want to actually experience the city, not just photograph it.

Additional information:

• Includes three food tastings (two pizza styles, prime steak, and a Chicago-style hot dog), plus water and soft drinks throughout.

• The tour covers approximately 1 mile with four stops. Flat terrain, suitable for most fitness levels.

• Tour departs rain or shine. Dress for the weather and wear comfortable walking shoes.

• Tastings are portioned to equal a good lunch. No need to eat beforehand.