Small-group moments with real support

Private Chicago Mafia and Blues Evening Tour

Get a guided experience designed around how you want to spend your time in Chicago , Illinois. You’ll receive clear booking details, straightforward inclusions, and a quick reply from a real person.

2 hours 30 minutes (approx.) (approx.)
Max 5 travelers
English language

The offer

Pay a fixed price upfront and get confirmation details when available. If you have accessibility needs or dietary restrictions, include them—we’ll do our best to accommodate.

Request now

Highlights

  • Confirmation details provided during booking
  • Wheelchair and stroller friendly
  • Most travelers can participate—tell us what you need
Service animals allowed Surfaces are wheelchair accessible

City context

This experience is paced for real-life travel—time to enjoy, time to ask questions, and space to take in Chicago through local flavor and stories.

Time-friendly itinerary Local storytelling focus Small-group atmosphere

Meeting address is shared with confirmation so you know exactly where to be.

Included

What you can expect during the experience.

    Bottled water Driver/guide Hotel pickup and drop-off Transport by private vehicle

Not included

A few practical notes so there are no surprises.

    Alcoholic drinks (available to purchase) Gratuities

Detailed tour information

A well-paced itinerary built for guests who want quality time, not rushing.

Travel back in time to learn about life in Chicago in the 1920s, 30s, and 40s on this private, 2.5-hour sightseeing tour. Learn about the mafia, blues music, plus the city's scandals, sports teams, and more. Then explore the current nightlife scene in the Windy City.
  • Historic Chicago sightseeing tour of the 1920s-1940s
  • Learn about the mafia, blues music, scandals and more
  • Explore the current nightlife scene in Chicago
  • Private guide ensures personal attention

What To Expect

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Chicago Travel & Tours

Tour privativo organizado pela Chicago Travel & Tours

• Admission Ticket Free

Green Mill

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Northalsted

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Wrigley Field

Tour privado, podemos personalizar o tour de acordo com sua expectativa

• Admission Ticket Included

Lincoln Park

Tour privado, podemos personalizar o tour de acordo com sua expectativa

• Admission Ticket Included

What makes this special

Thoughtful guidance, genuine local context, and an emphasis on comfort—so you can relax into the experience.

Top highlights

    Confirmation will be received within 48 hours of booking, subject to availability Minimum age is 21 years May be operated by a multi-lingual guide Not wheelchair accessible A minimum of 3 people and a maximum of 12 people is required per booking A current valid passport or government-issued ID is required Near public transportation Duration includes hotel pickup and drop-off Most travelers can participate Tour offered in Portuguese only This is a private tour/activity. Only your group will participate

Practical city guidance

Chicago , Illinois travel can be busy. We recommend arriving a few minutes early for an unhurried start. If you’re traveling with dietary needs, allergies, or accessibility requirements, add them to your request—this helps us confirm the details for your group.

Share allergies in your message Ask about accessibility needs We’ll confirm meeting logistics

Clear expectations

Know what’s included and what isn’t before you request. We keep details simple and easy to review.

Human support

Send your questions with confidence—your request is handled by people who answer like real humans.

Comfort-first pacing

Designed for small groups with practical timing so you can enjoy the neighborhood without stress.

FAQ & practical guidance

Quick answers to help you plan confidently.

Choose your preferred date and share your group details. After your request is received, confirmation and meeting details are provided when booking is confirmed.
Yes—include allergies, dietary preferences, and any restrictions in your message. We’ll do our best to accommodate where possible.
Many guests participate comfortably. If you’re traveling with a stroller, require wheelchair access, or have other accessibility notes, tell us in advance so we can confirm details.
Just come ready to enjoy. If you have any allergies, we recommend mentioning them again when you arrive. Comfortable shoes help, and a phone is useful for meeting-day coordination.

Your request, your pace

Tell us what matters most—then we’ll confirm details so you can relax.

  • Clear inclusions and notes before you book
  • Meeting logistics shared at confirmation
  • Support available for questions and special needs

Prefer help choosing the best date? Use the form and include your arrival window—we’ll respond with practical guidance.

Request this experience

We’ll review your details and reply with confirmation and next steps by email. Please fill everything in so we can match you with the right plan.

Questions first?