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Chicago Gangster and Food Walking Tour

4.8 (285)
Chicago, US
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Chicago Gangster and Food Walking Tour

4.8 (285)
Chicago, US
Share
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Experience the thrilling side of Chicago with the Gangster and Food Walking Tour. Immerse yourself in the Prohibition Era as you indulge in the city's most iconic dishes and explore the stomping grounds of infamous gangsters. Delight your taste buds with prime steak, deep dish pizza, and the world-famous "Chicago hot dog". As you walk through the historic neighborhoods, discover hidden secrets like an old tunnel used by prohibition gangsters. Feel the excitement in the air as you visit locations like Harry Caray's steak house, a former hideout for Al Capone's men. Marvel at the bullet holes from a Tommy Gun on the side of Holy Name Cathedral, where a notorious gangster was gunned down. Cross the iconic Chicago River and capture stunning photos of the city's skyscrapers. Don't miss this unique tour that combines Chicago's world-famous cuisine and captivating gangster history.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 2 hours
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Guided Experience
  • "Taste iconic Chicago foods"
  • "Explore Prohibition era neighborhoods"
  • "Visit gangster hideouts and secret tunnels"
  • "Experience Chicago's famous deep dish pizza"
  • "Learn about Chicago's gangster history"
  • Lunch
  • Alcoholic beverages
  • Tour Guide Gratuity

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More about this experience

Introduction

Experience the thrilling Prohibition Era in Chicago with the Chicago Gangster and Food Walking Tour. This unique tour takes you through one of the most fashionable and notorious neighborhoods of the time while indulging in Chicago's iconic cuisine. From prime steak to deep-dish pizza and the famous "Chicago hot dog," taste the flavors that made this city famous. As you walk the streets once frequented by Al Capone and his gang, uncover the secrets and stories behind the prohibition era. Get ready to step into the underworld of Chicago and satisfy your taste buds on this one-of-a-kind tour.

What to expect?

On this tour, expect to immerse yourself in the history and flavors of Chicago. Lasting for 120 minutes, the itinerary takes you through different steps of gastronomic pleasure. You'll start in the River North neighborhood, home to iconic restaurants and significant gangster history. Indulge in prime steak at Harry Caray's steakhouse, once an Al Capone hideout with a secret tunnel used by gangsters. Savor deep-dish pizza in an old gangster's mansion turned iconic pizzeria. Then, head to the historic Gold Coast neighborhood to try the famous "Chicago Dawg" at one of the oldest serving establishments. Along the way, stop at the Holy Name Cathedral, where a notorious gangster was gunned down in the 1920s. Take in the sights as you cross the Chicago River, surrounded by stunning skyscrapers.

Who is this for?

This tour is perfect for anyone with a love for history, food, and adventure. Whether you're a local wanting to explore your city in a new way or a visitor looking for an authentic Chicago experience, this tour is for you. It's an opportunity to discover Chicago's culinary heritage while learning about its infamous past. The tour is designed to be inclusive and enjoyable for people of all ages and backgrounds. Whether you're a solo traveler, part of a group, or on a romantic getaway, come join us to uncover the secrets and flavors of Prohibition-era Chicago.

Why book this?

Step back in time and dive into the captivating world of Chicago's gangster history on this immersive food walking tour. Not only will you taste the iconic foods that put Chicago on the map, but you'll also walk in the footsteps of notorious gangsters and visit locations that played a significant role in the Prohibition Era. Let your senses be awakened by the rich flavors, tantalizing aromas, and compelling stories that have shaped this city. With a passionate and knowledgeable guide leading the way, every step will be filled with excitement and intrigue. This tour is a chance to experience the best of Chicago's cuisine while uncovering the hidden tales of its past, making it an unmissable opportunity for both locals and visitors alike.

Good to know

Please note that the total duration of the tour is 120 minutes. The meeting point is in front of "Hoyt's" at the Royal Sonesta Hotel, conveniently located across from the Chicago River. The tour takes you through various neighborhoods, providing not only delicious food stops but also opportunities for sightseeing and exploration. The tour ends just two blocks from the Magnificent Mile, a vibrant area perfect for continuing your Chicago adventures. Don't forget to wear comfortable shoes and bring along your appetite as you embark on this fascinating journey through Chicago's history and cuisine.

Reviews

Feedback from previous participants attests to the exceptional experience offered by the Chicago Gangster and Food Walking Tour. Visitors have raved about the knowledgeable guides, who bring the stories and history to life, making the tour engaging and entertaining. The combination of delicious food and intriguing tales makes for an unforgettable outing. Travelers have praised the selection of food stops, from the legendary Harry Caray's steakhouse to the mouthwatering deep-dish pizza served in a historic gangster's mansion. The opportunity to visit significant locations, such as the Holy Name Cathedral and crossing the Chicago River, has been mentioned as highlights of the tour. Overall, reviews highlight the tour as a must-do in Chicago, providing a unique and immersive experience that blends history, culture, and cuisine seamlessly.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Your Itinerary

River North

Chicago's famous River North neighborhood containing many of Chicago's most iconic restaurants, food and gangster history. Travelers will eat at Harry Caray's steak house, an old hideout for Al Capones men with a secret tunnel used by gangsters in the 1920s and 1930s which the guests will see. Also we will have deep dish pizza in an old gangster's mansion that was converted years ago into one of Chicago's most iconic Pizzeria restaurants.

Gold Coast

Try Chicago's iconic "Chicago Dawg" at one of it's oldest serving establishments in the beautiful and historic Gold Coast neighborhood.

Holy Name Cathedral

On route to one of our food stops we will stop in front of this beautiful church where one of Chicago's most notorious gangsters was gunned down in the 1920s. The bullet holes from the Tommy Gun are still visible in the side of the church today! Hear the story on our tour!

Chicago River

Guests will get to cross the Chicago River on this tour with all its many skyscrapers. Great for Photo Ops!

Reviews

(285)

4.8 (285)

Maira_M

Baylor was a phenomenal guide!! Took the time to answer all questions and explain the rich Chicago Mob history! Baylor gave great recommendations as well. Definitely one of my favorite tours!

Sergio_P

Thank you to Ty for a great couple of hours learning about Chicago's colorful past. Lots of information and interesting stories mixed with a nice sampling of food. Would recommendas a way to spend an afternoon in Chicago.

Mindy_L

We had a blast learning about the history of Chicago gangs and stopping to eat on the way. Alan was knowledgeable and engaging. He had all the answers to any questions my kids had to ask. Great steak, awesome pizza experience and very cool hotdogs, too. I would recommend this to anyone visiting Chicago! Be ready for a nice walk!

Ginny_B

Alan was very knowledgeable. The food was amazing. I highly recommend this tour for people wanting to taste the local fare amd learn about the history of the area

Natalia_R

Cool walking tour! They take you places to ear you wouldn’t think of trying and taste some great food. And you get to learn about the history of Chicago. Avery was a great guide!

Kristina_B

Alan was fantastic - the only thing I wish is a private tour would have been an option when booking there were 8 of us for a business team building event and a random couple from WI.

donitab225

Great time learning about Chicago food and its history as well as some serious gangster action. Sarah did a great job and we enjoyed all the members in our tour group. Highly recommend!

JON_R

Alan was great! Knowledgeable, well-spoken, funny and just a really good guy. The food was also outstanding and was such a great representation of Chicago.

Holly_M

I loved Alan's story telling and knowledge of the history of Chicago. The delicious food was a bonus! We were able to try the classics from a different place than where we had already been. Putting these on my list for next time!

shannondJ8522GF

Unique way to get a bit of history while trying some of the staples of Chicago cuisine! Baylor was a super informative guide in terms of going through the Gangster history as well as providing advices on various activities to do in Chicago.
Collected by Evendo, Tripadvisor & Viator
2024-04-29 18:39