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Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour

8 Reviews 4.63 out of 5 stars Based on 8 reviews collected by Key West Private Charters and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
| Chicago, USA
Book online or call us

from $8.99 per person

Lowest Price Guarantee
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Don't miss out!
On average, this is booked 21 (0) days in advance.
50 minutes (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

Where did Chicago’s millionaires live, love and misbehave? Walk the Gold Coast with historian Amy Bizzarri, author of 111 Places in Chicago That You Must Not Miss. This self-guided tour is great value for money!

Start at Lincoln Park’s last surviving grave, stroll mansion-lined Astor Street and hear about the Pump Room’s celebrity booth, a ghoulish surgical museum and Jane Addams’ artists’ club. The tour ends at the Zebra Lounge, a hidden piano bar that has had live music since 1929. Step inside for a Faster Pussycat martini and sing along. GPS audio plays automatically and works offline, so your phone stays in your pocket.

Highlights:
- 1.3-mile walk narrated by a Chicago author and historian
Peek through the gates of Hugh Hefner’s original Playboy Mansion.
- Walk one of Chicago’s last 19th-century wooden block alleys.
- Finish with a cocktail at the Zebra Lounge, playing live piano since 1929.
- Pause for a drink and pick up where you left off, with lifetime access.

What's Included

  • Directions to the starting point so that when you're in the right place, the tour will start
  • Lifetime access to this tour in English before your booking date and after it
  • Offline access to audio, maps, and geodata
  • Smartphone & Headphones
  • Transportation
  • Food/Drink
See 3 moreSee 4 more

Meeting Location

Meeting point

1601 North Clark Street
Chicago, IL 60614, USA

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

1220 North State Parkway
Chicago, IL 60610, USA

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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Safe & secure Easy breezy Hassle‑free

Chicago History Museum (pass by)

Your tour starts outside Chicago’s oldest cultural institution, at the edge of Lincoln Park. Amy Bizzarri introduces the Gold Coast, the lakefront neighborhood that became the city’s most glamorous address after the Great Fire of 1871. It’s easy to reach by CTA bus or the Red and Brown Lines. PLEASE NOTEL Any entrance fee is not included.
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Couch Mausoleum (pass by)

This is Lincoln Park’s eeriest secret. The park was once the city cemetery, and thousands of bodies are still believed to lie beneath it. One tomb survived: the limestone vault of early millionaire Ira Couch. Its huge stones are riveted together with copper, which made it far too costly to move.
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Lincoln Monument Gardens (pass by)

The Standing Lincoln Stature - Pass Augustus Saint-Gaudens’ larger-than-life bronze of Abraham Lincoln, unveiled in 1887 and considered one of the finest statues of the 16th president in the country. It’s a fitting landmark as you head out of Lincoln Park toward the mansions of the Gold Coast.
Read more

Archdiocese Of Chicago- Cardinal Mansion (pass by)

Built in 1885 for Chicago’s first Catholic archbishop, this red-brick Queen Anne residence is one of the oldest buildings in the Astor Street District. Seven archbishops have called it home. Try to count all 19 chimneys from the sidewalk. Only three of them still work.
Read more

Lake Shore Drive (pass by)

Stroll the lakefront boulevard that Potter Palmer’s money helped create from swampland. Hear the story behind the ’70s hit song “Lake Shore Drive” and the double meaning in its lyrics that the songwriter always denied. Keep an eye on Lake Michigan as you walk.
Read more

International Museum of Surgical Science (pass by)

This 1917 lakefront mansion was modeled on the Petit Trianon at Versailles. Inside are four floors of medical history, from bloodletting tools to a gallery of trephined skulls with holes drilled to release “evil spirits.” It’s ghoulish and fascinating, and worth a visit inside if you have time.
Read more

Burton Place (pass by)

Learn how the Gold Coast was born. In 1882, hotel tycoon Potter Palmer built a castle-like mansion on swampy land beside the lake, and Chicago’s wealthiest families soon followed him north. Today the neighborhood is still one of the richest in urban America.
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North Astor Street (pass by)

Walk down what many call Chicago’s most beautiful residential street. It’s lined with 19th-century townhouses and mansions in a mix of grand revival styles. Look up at the carved stone, turrets and ironwork, and imagine the city’s elite arriving home by horse and carriage.
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Chicago's Wood Block Alley (pass by)

Step onto a street surface that hasn’t changed since horse-drawn days. In 1871 Chicago had 37 miles of wooden block paving, which was quieter under hooves than stone. Only a few stretches survive, and this is the best of them. Hear why it was slippery and smelly, and why it didn’t burn.
Read more

Original Playboy Mansion (pass by)

Hugh Hefner bought this 70-room 1899 mansion in 1959. The door once read “Si Non Oscillas, Noli Tintinnare” (“If you don’t swing, don’t ring”), and the basement had a pool with a glass wall. Find out why Hefner suddenly left Chicago for Los Angeles in 1974.
Read more

3 Arts Club Cafe at RH Chicago (pass by)

Jane Addams co-founded this Byzantine-style building in 1912 as a safe, affordable home for young women studying music, painting and drama. More than 13,000 artists lived here. Today it’s a Restoration Hardware gallery. Step inside to see the sunlit central courtyard, now a café.
Read more

Zebra Lounge (pass by)

An outstanding Chicago night out on the town always ends piano side, sipping Lemondrops and singing along with the piano man into the wee hours at the Zebra Lounge. Hidden in the lobby of a vintage apartment building in the glam Gold Coast, the Zebra Lounge has been swinging with live piano players seven nights a week since 1929.
Read more
Show 11 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Chicago’s Gold Coast Hidden History: A Self-Guided Audio Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-110804P96

Traveler Photos

Reviews

4.63
8 reviews

Average 4.63 out of 5 stars based on 8 traveler reviews collected by Key West Private Charters and partner sites such as Cool Destinations and TripAdvisor

5 stars
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Don't miss out!
On average, this is booked 21 (0) days in advance.
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Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Key West Private Charters customers.

Filter by:

Q: What is the cancellation policy for the Chicago’s Gold Coast Hidden History: A Self-Guided Audio Tour?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (CST).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Directions to the starting point so that when you're in the right place, the tour will start.
  • Lifetime access to this tour in English before your booking date and after it.
  • Offline access to audio, maps, and geodata.
  • The VoiceMap App for Android and iOS.
  • Flexibility to explore at your own pace with a self-guided GPS tour.
The following is NOT included:
  • Smartphone & Headphones.
  • Transportation.
  • Food/Drink.
  • Tickets or entrance fees to any museums or other attractions en route.
Apr 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 6..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Chicago's Gold Coast Hidden History: A Self-Guided Audio Tour is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago’s Gold Coast Hidden History: A Self-Guided Audio Tour will be included in your confirmation email from Key West Private Charters. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Directions to the starting point so that when you're in the right place, the tour will start
  • Lifetime access to this tour in English before your booking date and after it
  • Offline access to audio, maps, and geodata
  • The VoiceMap App for Android and iOS
  • Flexibility to explore at your own pace with a self-guided GPS tour
  • Smartphone & Headphones
  • Transportation
  • Food/Drink
  • Tickets or entrance fees to any museums or other attractions en route

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Infants are required to sit on an adult’s lap

Report Product Issue

Activity name