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Explore Chicago's Dark History: Explore Gangster Hideouts, Ghosts, & Iconic Food Tours w/ Walking or Minibus Tours

Chicago Ghosts and Gangsters Tours - Chicago, IL
4.7
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Laura
34 days ago
Lilly was amazing. My husband and I went in February in the cold at 8 pm and we both agree the tour was the highlight of our trip. Lilly was so engaging we forgot about the cold. Excellent story telling with a slash of humor. We were the only ones on this Monday night tour and Lilly went above and beyond. Thank you Lilly.

Immersive tours for those eager to delve into Chicago's notorious past, revealing tales of infamous gangsters, chilling ghost stories, and the city's iconic culinary scene.

Highlights

  • Immersive Storytelling: Expert local guides captivate with true tales of Chicago's gangster past and eerie ghost legends, bringing history vividly to life.

  • Culinary Exploration: Savor three iconic Chicago food tastings, including deep-dish pizza, hot dogs, and prime steak, on a unique walking tour.

  • Exclusive Access: Step inside historic gangster hideouts and haunted landmarks, offering a unique perspective on the city's notorious history.

  • Flexible Tour Options: Choose from guided walking tours or a luxury minibus experience, ensuring a comfortable and engaging journey through Chicago's most intriguing spots.

  • Perfect for gifting! An unforgettable experience for history buffs and thrill-seekers, easily giftable for friends, family, or fellow adventurers.

  • Alcoholic drinks

  • Luggage or large bags

What To Expect

Step back in time as Chicago Ghosts and Gangsters Tours unveils the city's shadowy past, allowing visitors to immerse themselves in true crime stories and spine-chilling ghost legends. Guests will walk the same streets where notorious figures like Al Capone once roamed, discovering secret tunnels, opulent brothels, and the sites of infamous gangland hits. The expert historian guides paint a vivid picture, ensuring every turn reveals a fascinating, often unsettling, piece of Chicago's dark history, from the bustling River North to the eerie South Loop.
What to expect media
Whether indulging in iconic Chicago deep-dish pizza and hot dogs on a food-tasting walk, or comfortably exploring key sites like the Congress Hotel and Art Institute from a luxury minibus, each tour promises a unique adventure. Guests will hear tales of hauntings at the Palmer House and Chicago Theatre, gaining exclusive insight into locations where gangsters conducted deals or met their grim ends. They offer a journey filled with historical intrigue and culinary delights, designed to entertain and educate every visitor.

Plan Your Visit

  • Operating Hours
    Hours may vary. Please check the merchant's website for the most up-to-date information.
  • Duration
    The Chicago Gangsters and Food Tasting Walking Tour lasts 2 hours. The Chicago Gangsters and Ghosts Guided Walking Tour involves approximately 1.5 miles of walking with a 20-minute break.
  • Accessibility
    Accessibility varies by tour
    the Chicago Gangsters and Food Tasting Walking Tour is wheelchair accessible, while the Luxury Minibus Tour is not suitable for wheelchair users. The Guided Walking Tour is not recommended for people with mobility impairments or infants.
  • Departure & Arrival
    The Luxury Minibus Tour offers convenient pick-up and drop-off services at the Palmer House.
  • Meeting Point
    Meeting points vary by tour. The Gangsters and Food Tasting Walking Tour and the Gangsters and Ghosts Guided Walking Tour meet outside Hoyt's Restaurant/Tavern at the Royal Sonesta Hotel on the Chicago River (cross streets Wacker and Wabash). The Luxury Minibus Tour meets at the Palmer House, Wabash Street Entrance.
  • Key Stops
    Tours visit iconic Chicago landmarks and historic sites such as Death Alley, Chicago Riverwalk, the Palmer House, Chicago Theatre, Congress Hotel, Holy Name Cathedral, Frank Nitti’s secret vault at Harry Caray’s, and the Jeweler’s Building.

Ticket Options

Chicago Gangsters and Ghosts Guided Walking Tour

A guided historical walking tour through Chicago's South Loop, exploring true tales of gangster history, Al Capone's empire, and eerie ghost legends at haunted landmarks like Death Alley, Chicago Riverwalk, the Palmer House, Chicago Theatre, and the Congress Hotel.

PLUS:Includes visits inside the Congress Hotel and Palmer House.

Chicago Gangsters and Food Tasting Walking Tour

A culinary and historical walking tour through Downtown Chicago's notorious River North neighborhood, combining tastings of iconic Chicago foods like deep-dish pizza, hot dogs, and prime steak with stories of famous gangsters and visits to their old hideouts and an underground tunnel.

PLUS:Features three food tastings (deep-dish pizza, tavern-style pizza, prime steak, Chicago hot dog) with water and soft drinks.

Chicago Gangsters and Ghosts Luxury Minibus Tour

A comfortable, guided luxury minibus tour exploring Chicago's notorious crime history and chilling ghost tales across the Loop and River North neighborhoods. Visit iconic sites like the Art Institute, Chicago Theater, Palmer House, Congress Hotel, Holy Name Cathedral, Frank Nitti’s secret vault at Harry Caray’s, and the Jeweler’s Building.

PLUS:Includes one stop at Harry Caray’s Italian Steakhouse and convenient pick-up/drop-off at the Palmer House.

How It Works

1. Plan your visit

Select and reserve your preferred date.

2. Grab the Deal

Proceed to checkout to buy & book your Groupon!

3. Redeem your Mobile Ticket

Scan your Groupon upon arrival.

4. Enjoy the Experience!

FAQs

What should visitors bring on the walking tours?

Visitors should bring comfortable shoes for the walking tours. It is also recommended to bring water and wear comfortable clothes, as tours depart rain or shine.

Are the tours suitable for all ages or mobility levels?

Suitability varies by tour. The Chicago Gangsters and Food Tasting Walking Tour is wheelchair accessible. However, the Chicago Gangsters and Ghosts Guided Walking Tour is not recommended for people with mobility impairments or infants, and the Luxury Minibus Tour is not suitable for wheelchair users. Children aged 6 and under can join the Guided Walking Tour for free.

What types of food are tasted on the Chicago Gangsters and Food Tasting Walking Tour?

The tour includes tastings of Chicago's iconic deep-dish pizza, historic tavern-style pizza, prime steak, and the world-famous "Chicago hot dog." Water and soft drinks are also provided.

Where do the tours typically meet?

Meeting points differ based on the chosen tour. The Gangsters and Food Tasting Walking Tour and the Gangsters and Ghosts Guided Walking Tour generally meet outside Hoyt's Restaurant/Tavern at the Royal Sonesta Hotel. The Luxury Minibus Tour meets at the Palmer House, Wabash Street Entrance, and also provides drop-off at this location.

What historical figures and sites are highlighted during the tours?

The tours highlight figures like Al Capone and explore sites such as old gangster hideouts, speakeasies, an underground tunnel used by Capone, Death Alley, the Chicago Riverwalk, the Palmer House, the Chicago Theatre, the Congress Hotel, Holy Name Cathedral, Frank Nitti’s secret vault at Harry Caray’s, and the Jeweler’s Building.

Need To Know Info

Promotional value expires May 7, 2030.
  • 3-day hassle-free refund guarantee - Free cancellation for up to 3 days after purchase for unredeemed vouchers.
  • Limit 5 per person.
  • May be repurchased every 180 days.
  • Online booking only.
Merchant is solely responsible to purchasers for the care and quality of the advertised goods and services. Learn about Strike-Through Pricing and Savings

About Chicago Ghosts and Gangsters Tours - Chicago, IL

During the Roaring 20s, Chicago's business district served as the stomping grounds for Al Capone and other historic gangsters. Today, the district, known as the Loop, still contains remnants of that bygone time, and the Gangsters and Ghosts Tour exposes guests to those gangster gems. Each night's walking tour starts near Wyndham Grand Chicago Riverfront hotel and explores 1.5 miles over about two hours. During the tour, an historian leads guests to famous and little-known spots that once housed underground tunnels and speakeasies, relaying verified ghost stories along the way.

Company Website

Customer Reviews

4.7
based on Groupon 882 reviews
100% Verified Reviews
All Groupon reviews are from people who have redeemed deals with this merchant. Review requests are sent by email to customers who purchased the deal.
Reviewed on
Laura
1 rating|1 review
Lilly was amazing. My husband and I went in February in the cold at 8 pm and we both agree the tour was the highlight of our trip. Lilly was so engaging we forgot about the cold. Excellent story telling with a slash of humor. We were the only ones on this Monday night tour and Lilly went above and beyond. Thank you Lilly.
Christine
2 ratings|1 review
Went in January and was not disappointed. Our guide, Max, was very informative and kept the tour interesting and engaging.
Mikayla
Top Reviewer
Helpful Reviewer
15 ratings|12 reviews
This tour was awesome! We selected the bus tour, because those Chicago winters are COLD! The guide stopped multiple times so that we could get out and fully explore a few spots. The tour was well done and the driver had extensive knowledge of the gangsters, ghosts, and Chicago in general. Highly recommend!
Guest
1 rating|1 review
Alan was a great tour guide! He was fantastic at telling stories.
Maddie
1 rating|1 review
Adam the tour guide was fantastic! Very nice and knowledgeable

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