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THE BEST OF CHICAGO TOUR $1,200.00

CHICAGO NIGHT GANGSTER TOUR

(3 customer reviews)

$900.00

Travel straight to the Prohibition Era, explore the famous historic neighborhoods, and learn true crime stories.

DURATION
3 hours		 TOUR TYPE
Private tour, your party only
GROUP SIZE
Up to 6 people. Please contact us for larger groups.		 PICKUP POINT
Your hotel or Airbnb

BOOK NOW

*Free Cancellation up to 24 hours before the tour

*Book Today and receive an Ultimate Chicago Restaurants Guide

PLEASE NOTE: As we operate a boutique luxury tour company with only the best hand-picked local guides, we highly recommend you to make a tour reservation as soon as possible to get your preferred date and time slot and avoid missing out!

Overview

This fantastic 3-hour evening adventure will take you back 100 years ago straight to the Prohibition Era.

Your journey will start right at the doorsteps of your hotel or Airbnb, where our friendly and knowledgeable tour guide will pick you up in a luxury vehicle. You will learn true crime stories about Chicago Gangster Al Capone, The Untouchables, The Chicago Mob, Cap George Streeter, Leopold & Loeb, H.H. Holmes, John Dillinger, Frank “The Enforcer” Nitti, and many others. You will see the district where the 1920s and 30s, shady partying, deal-making, and threats took place daily.

Next, you will tour historic neighborhoods like The Old Town, The Loop and Magnificent Mile, River North, Lincoln Park, and Streeterville. You will visit the landmark buildings like Cook County Criminal Courthouse, Harry Caray’s Italian Steakhouse, Biograph Theater, and Holy Name Cathedral. Finally, you will explore the famous crime scenes with amazing photo ops!

HIGHLIGHTS

  • Congress Hotel
  • Death Alley
  • Palmer House
  • Biograph Theater
  • Holy Name Cathedral
  • Cook County Criminal Courthouse
  • Harry Caray’s Italian Steakhouse

WHAT’S INCLUDED

  • Private tour, your party only
  • Luxury vehicle
  • Complimentary pick up at select locations
  • Knowledgeable tour guide
  • Bottled water
Reviews(3)

3 reviews for CHICAGO NIGHT GANGSTER TOUR

  1. Sadie –

    Ben was an awesome storyteller, and this was my 4th tour with USA VIP TOURS during the trip. All were super great! But this one truly brought the history to life. I would say this is a must if it’s your first time visiting the Chicago.

  2. Eric and Virginia –

    Our tour guide William was knowledgeable, fun and kept us fully engaged the entire time! We learned about the city and its spookiness, and the rise and fall of Al Capone. We really felt like we time-traveled to the past when listening to the stories. We thoroughly enjoyed our experience.

  3. Genesis –

    Absolutely recommend doing this if you’re in Chicago. We had the best time exploring the city and listening to its infamous history. Good stops with interesting points. Our guide Roman was very enthusiastic and entertaining, he shared so many facts about the prohibition era, gangster life and Chicago disasters with us. Thank you! We will recommend this tour to all of our friends and family.

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Why Choose Us
OUR TOURS ARE FULLY CUSTOMIZABLE

Every guest is unique, so we try to find out your needs and preferences before the trip, to be able to draw up a tailored to perfection tour experience.

WE ONLY USE EXECUTIVE TYPE VEHICLES

We always put your comfort first and make sure you get the best seat in the house with our state-of-the-art luxury sedans, max size SUV’s and Mercedes Sprinter vans.

WE FOLLOW STRICT HEALTH PROTOCOLS

All of our guides are up to date with their vaccinations, and thoroughly sanitize the vehicles between each tour. We also provide masks and hand sanitizers for your convenience.

WE LOVE TAKING PICTURES

We know photos are important, so we take you to the best picture-perfect spots and capture those wonderful moments for you to remember.

WE GIVE USEFUL RECOMMENDATIONS

Our tours don’t “end” when the time’s up, we give you tons of suggestions on what to do in your free time, and you’re always welcome to reach out to us even after the tour.

WE STRIVE FOR COMPLETE CUSTOMER SATISFACTION

Our goal is to ensure that you have the most amazing, highly personalized and stress-free experience full of fun with everlasting memories.

FAQ
WHAT KIND OF VEHICLES DO YOU USE FOR THE TOURS?

We always put your comfort first and make sure you get the best seat in the house with our state-of-the-art luxury sedans, max size SUVs and Mercedes Sprinter vans.

DO YOU USE A DRIVER-GUIDE OR A GUIDE + A DRIVER?

Our tour guides are also drivers, but if you prefer to have a separate driver, we can organize it for an additional charge.

DO YOU DO TOURS IN ENGLISH ONLY?

No, other languages are available upon request.

DO YOU PROVIDE CAR SEATS FOR CHILDREN?

Yes, we do, free of charge.

ARE YOUR TOURS APPROPRIATE FOR KIDS?

Yes, all of our tours are appropriate for children. We love having kids on our tours, and we find that they truly enjoy the experience. We have booster and child seats available upon request, free of charge.

HOW MUCH WALKING DO WE DO DURING THE TOURS?

As we do highly personalized private tours we always put your comfort first and make sure you enjoy the pace. You can do as much or as little walking as you want. But please let us know in advance if you have any mobility issues.

WHAT TIME DO YOU USUALLY START THE TOURS?

As all of our tours are private we do not have any specific time frames to start or finish the tours. It is really up to you to choose the time slot that works best for your group.

WHERE DO YOUR TOURS START?

We usually pick you up from your hotel or Airbnb, but we can also do airport or cruise terminal pick-ups and drop offs at an additional charge.

WHAT DO I NEED TO TAKE ON THE TOUR?

We recommend that you take your credit card for anything you would want to purchase during the tour (such as coffee, souvenirs, etc.), ID, a hat and sunscreen on a hot day.

IS GRATUITY INCLUDED?

If you feel that the tour guide met or exceeded your expectations you are welcome to reward him/her as an expression of your appreciation. Leaving a gratuity is at your discretion, and the standard gratuity in the service industry is 15-20%.

WILL THERE BE STOPS ON THE TOUR?

Of course! We will make as many stops as you’d like, our tours are highly personalized and we will make sure it is tailored to your specific needs and preferences.

WILL YOUR TOUR GUIDE TAKE PICTURES?

We love taking pictures and we know how important they are, so we take you to the best picture-perfect spots and capture those wonderful moments for you to remember.

DO YOU SHOW OFF-THE-BEATEN PATH SPOTS?

With our deep understanding of all the insider secrets to the best sights, you are sure to be taken to the right place at the right time, both bucket-listers and hidden gems.

WILL WE HAVE TIME FOR LUNCH ON THE TOUR?

It depends on the length of the tour and your preferences. The tour time is YOUR time, and you can choose to have a short coffee stop or a nice lunch in the restaurant, no rush, we want your experience to be perfect!

WILL THE TOUR GUIDE GIVE SOME RECOMMENDATIONS ON WHAT TO DO IN OUR FREE TIME IN THE CITY?

Our tours don’t "end" when the time’s up, we give you tons of suggestions on what to do in your free time, and you’re always welcome to reach out to us even after the tour.

CAN YOU ORGANIZE THE WHOLE USA TRIP FOR ME?

Yes, we do that for our guests all the time! Our team will take care of everything from helping you plan your trip to actually assisting you with anything you may need while you are here. We leverage on the exceptional relationships that we trust with the best USA luxury resorts, 5-star hotels, magnificent villas, talented local guides, luxury transportation, cruising & yachting, private aviation charters, and exclusive events. Let us help you transform your USA vacation into something really unique and unforgettable!

Got Questions?

There are four fast and easy ways to contact us:

CALL or TEXT

+1 (800) 760 0092

WHATSAPP or VIBER

+1 (818) 568 8875

EMAIL

contact@usaviptours.com

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