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Willis Tower

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Chicago Riverwalk

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United Center

Wrigley Field

Landmarks & monuments

Viewing points

Day trips

Museums & exhibitions

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  • Top experiences
  • Interests
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Architecture

Bus & minivan tours

Lights tours

TV & movie tours

Ghost & vampire tours

Dinner & lunch cruises

Boat parties

Speed & jet boat tours

Dinner shows

Sailing trips & boat tours

Hop-on Hop-off tours

City cards

Explore more things to do in Chicago

Sightseeing

Culture & history

Food & drinks

Outdoor activities

Rainy-day activities

Outdoor sports

Water sports

Nature & adventure

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Explore more things to do in Chicago

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48 hours in Chicago

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Chicago travel guide

Chicago: Prohibition-Era Culture & Architectural Treasures

Top rated
4.7471266 out of 5 stars
4.7
4.7471266 out of 5 stars
87 reviews
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Chicago: Prohibition-Era Culture & Architectural Treasures
Top rated
4.7471266 out of 5 stars
4.7
4.7471266 out of 5 stars
87 reviews

Walk Chicago to see the legacy left behind by the Prohibition Era. See the architecture, iconic sights (both old and new), and best spots and try a local sweet treat along the way.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Reserve now & pay later
Keep your travel plans flexible — book your spot and pay nothing today.
Duration 2.5 hours
Check availability to see starting times
Live tour guide
English
Private group available

Highlighted reviews from other travelers

M
Melisa – New Zealand

Rich was a great tour guide, he was very knowledgeable and it a great tour of Chicago highlights

M
Marcy – Canada

Our tour guide Bash was outstanding. He enthusiastically shared his love for Chicago and its history. This is a must tour for first timers to Chicago. We learned so much about the history, architecture and people who made Chicago.

Select participants and date

Participants

Itinerary

  • Timeline stop icon

    Starting location:

    The Chicago Theatre

  • Timeline stop icon

    Chicago Pedway

    Guided tour, Walk (20 minutes)

  • Timeline stop icon

    Chicago City Hall

    Guided tour, Walk

  • Timeline stop icon

    Chicago Picasso Statue

    Guided tour, Walk (10 minutes)

  • Timeline stop icon

    Chicago River

    Guided tour, Walk (20 minutes)

  • Timeline stop icon

    Chicago Riverwalk

    Guided tour, Walk (20 minutes)

  • Timeline stop icon

    Wrigley Building

    Guided tour, Walk

  • Timeline stop icon

    The Magnificent Mile

    Guided tour, Walk (10 minutes)

  • Timeline stop icon

    Millennium Park

    Guided tour, Walk (20 minutes)

  • Timeline stop icon

    Cloud Gate

    Guided tour, Walk

  • Finish at:

    Millennium Park

Main stop

For reference only. Itineraries are subject to change.

Highlights

  • Explore Chicago’s Prohibition-era legacy and iconic architectural landmarks
  • Stroll along the Riverwalk, discovering key buildings like Willis Tower
  • Visit the Chicago Cultural Center and enjoy a local Chicago-style popcorn treat
  • End at Millennium Park and the iconic Bean, with tips for lunch and sights
  • Receive personalized attention on a small-group tour with just 12 participants

Full description

Explore Chicago’s Prohibition Era legacy and how it shaped the city's growth and architecture. Learn about iconic buildings that reflect Chicago’s dynamic future and rich history.

Start at the Chicago Theater, then stroll along the Riverwalk, learning about key landmarks like Marina Towers, Willis Tower, and the Jewelers Building. Discover Art Deco designs at the London House and Du Sable Bridge.

Visit the Chicago Cultural Center, a stunning architectural gem, and enjoy a local treat of Chicago-style popcorn. Learn about the Wrigley Building, Tribune Tower, and the city’s historical roots in journalism.

End at Millennium Park, home to the iconic Bean sculpture, with your guide offering great recommendations for lunch and further sights.

Includes

  • Local English-speaking guide
  • Popcorn tasting
  • Gratuities

Meeting point

The Chicago Theatre (underneath the marquee), 175 N. State Street, Chicago, IL 60601

Open in Google Maps

Important information

What to bring

  • Comfortable shoes
  • Weather-appropriate clothing

Know before you go

  • This tour is carbon neutral, operated by a B Corp certified company committed to using travel as a force for good. This Certification measures a company’s social and environmental impacts and responsible tourism practices.
  • The maximum number of people on small group tour will be 16 passengers.
  • This is a child-friendly walking tour. Children under the age of 6 are permitted to join this tour free of charge.
  • Suitable for all ages and fitness levels, but please note that this tour covers about 4.8 km (3 miles) of walking.
  • Experiences happen rain, shine, or snow. Please dress accordingly.
  • We can accommodate vegetarian options but cannot accommodate other food allergies or dietary preferences. Please notify us in advance if you have any dietary requests.
Save up to 30%

From $49 $34 per person

Reserve now & pay later to book your spot and pay nothing today
Reserve now & pay later to book your spot and pay nothing today

Customer reviews

Overall rating

4.7 /5

based on 87 reviews

Review summary

  • Guide
    5/5
  • Value for money
    4.7/5
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M
Melisa – New ZealandMay 7, 2025 – Verified booking
Rich was a great tour guide, he was very knowledgeable and it a great tour of Chicago highlights
M
Marcy – CanadaMarch 17, 2025 – Verified booking
Our tour guide Bash was outstanding. He enthusiastically shared his love for Chicago and its history. This is a must tour for first timers to Chicago. We learned so much about the history, architecture and people who made Chicago.
M
Maria L – United StatesSeptember 24, 2024 – Verified booking
The tour guide was knowledgeable, patient and informative

Product ID: 243062

Activity provider:Intrepid Urban Adventures
  • United States
  • Illinois
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