See more
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Check availability to see start times.
English
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Meet at the starting point
Before arrival, please install the VoiceMap mobile app and use the code provided on your confirmation ticket. This is a self-guided audio tour that you can start, pause, or restart at any time and complete at your own pace. Detailed starting point instructions are available after downloading.
Open in Google MapsFor a full refund, cancel at least 24 hours before the scheduled departure time.
Your booking is confirmed immediately after checkout.
From $8.99 per person