Chicago Gangsters & Ghosts Tours with Food Tastings, Walking Tours, or Luxury Bus Experience

Gangsters and Ghosts Tour - Chicago
Chicago

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858 Groupon Ratings
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Highlights

Explore Chicago’s thrilling past with guided tours that blend food, history, and hauntings. Choose from a gangster-themed food tasting, a ghostly walking tour, or a luxury minibus adventure — all led by expert guides through the city’s most notorious neighborhoods.

About This Deal

Highlights

  • 2-hr to 3-hr guided experiences through Chicago’s gangster and ghost history

  • Taste Chicago’s signature foods including deep-dish pizza, tavern-style pizza, prime steak, and the iconic Chicago hot dog

  • Explore famous gangster hideouts, prohibition tunnels, and sites tied to Al Capone

  • Visit haunted landmarks like the Congress Hotel, Palmer House, and Death Alley

  • Comfortable, guided luxury minibus option for those who prefer sightseeing in style

What To Expect

Chicago’s gangster past and ghostly legends come to life on these immersive tours. On the Gangster Food Tasting Tour, you’ll sample Chicago’s most iconic bites while stepping into Al Capone’s old haunts, from prohibition tunnels to mob-owned mansions. It’s a feast of history and flavor that leaves you full in more ways than one.
What to expect image
Prefer chills over thrills? The Gangsters & Ghosts Walking Tour takes you through Chicago’s South Loop, revealing eerie tales of hauntings and infamous mob deals. Or, upgrade to the Luxury Minibus Tour, where you’ll relax in comfort while exploring the Chicago Theater, Palmer House, and the city’s most haunted hotel — the Congress. Each experience is led by knowledgeable local guides who make history both engaging and unforgettable.

Plan Your Visit

  • Meeting Point Food Tasting Walking Tour: Royal Sonesta Hotel – 71 E. Upper Wacker Drive
    Guided Walking Tour – Royal Sonesta Hotel – 71 E. Upper Wacker Drive
    Luxury Minibus Tour – Palmer House a Hilton, 17 E Monroe Street, Chicago, 60603
  • Operating Hours / Schedule Tours run daily with various start times; check availability at booking.
    Food Tasting Walking Tour: Daily at 11:15AM and 1:30PM
    Guided Walking Tour – Daily at 11AM, 1PM, 4PM, and 8PM
    Luxury Minibus Tour – Daily at 2PM, 4PM, 6PM and 8PM

Tour Options & Duration

Chicago Gangsters and Food Tasting Walking Tour

Savor Chicago’s iconic eats while exploring the streets once ruled by gangsters. From deep dish pizza to bullet-riddled landmarks, this tour blends bold flavors with gritty history for a truly immersive experience.
Duration: 2 hrs

Chicago Gangsters and Ghosts Guided Walking Tour

Uncover Chicago’s haunted past on a 2-for-1 Gangster & Ghost Tour—real crime scenes, eerie landmarks, and gripping stories led by expert guides.
Duration: 2 hrs

Chicago Gangsters and Ghosts Luxury Minibus Tour

Discover Chicago’s gangster and ghost stories on a guided minibus tour through the city’s most haunted and historic neighborhoods—spooky, scenic, unforgettable.
Duration: 2 hrs

How It Works

1. Grab the Deal

Proceed to checkout to buy & book your Groupon!

2. Redeem your Mobile Ticket

Scan your Groupon upon arrival.

3. Enjoy the Experience!

FAQs

What foods are included in the Gangsters Food Tour?

Guests enjoy Chicago staples such as deep-dish pizza, tavern-style pizza, prime steak, and the city’s signature Chicago hot dog. Water and soft drinks are included.

Are vegetarian options available on the Food Tour?

Yes, most stops can accommodate vegetarian requests. Be sure to note dietary needs when booking.

Is the Ghost Walking Tour family-friendly?

Yes, the Ghost Walking Tour is suitable for families and kids ages 6 and up. While stories may be spooky, they are presented in an engaging, family-friendly way.

Can children join the tours for free?

Children under 6 may join the Ghost Walking Tour free of charge. For other tours, reduced child pricing may apply — check at booking.

Where does the Luxury Minibus Tour start and end?

The Minibus Tour begins and ends at the Palmer House, Wabash Street Entrance. Guests enjoy sightseeing in comfort with a dedicated guide.

Are the tours wheelchair accessible?

The Food Tour is wheelchair accessible. The Ghost Walking Tour involves 1.5 miles of walking and may not be suitable for those with mobility issues. The Luxury Minibus Tour is not wheelchair accessible.

Fine Print

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. Offer is not eligible for our promo codes or other discounts. Learn about Strike-Through Pricing and Savings

About Gangsters and Ghosts Tour

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.

Groupon Customer Reviews

4.7
858 Groupon Ratings
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