Embark on a captivating journey through Chicago’s most illustrious addresses, where each step tells a story of architectural brilliance, historical grandeur, and cultural allure. From the soaring heights of 1150 Lake Shore Drive to the opulent corridors of the Original Playboy Mansion, this tour invites you to delve into the heart of the city’s rich heritage. Discover hidden stories behind iconic facades, walk the paths of the influential, and immerse yourself in the elegance that has shaped Chicago. This isn’t just a tour; it’s your gateway to experiencing the soul of a city that prides itself on architectural marvels and legendary tales. Make history your playground and become the hero of your own Chicago adventure with us.
A full-day private Napa County wine tour from Sacramento
Create a custom itinerary and visit just the wineries you choose
Travel in SUVs or luxury vans with room for six or eight passengers
Pickup and drop-off from anywhere in Sacramento and the surrounds
What To Expect
1150 Lake Shore Drive Building
Iconic skyscraper offering breathtaking Lake Michigan views; a marvel of modern architecture.
15 minutes • Admission Ticket Free
John Wellborn Root House
Historic residence of the famed architect; a glimpse into Chicago’s architectural heritage.
15 minutes • Admission Ticket Free
Ambassador Chicago – JDV by Hyatt
Elegant hotel embodying Chicago’s rich history and sophistication; a stay worth experiencing
15 minutes • Admission Ticket Free
North Astor Street
Prestigious street lined with architectural gems; a walk through Chicago’s elite history.
15 minutes • Admission Ticket Free
Charnley-Persky House Museum
Masterpiece showcasing the collaboration between Adler, Sullivan, and Wright; a cornerstone of architectural innovation.
15 minutes • Admission Ticket Free
Mc Cormick Mansion
Grandiose mansion reflecting Chicago’s Gilded Age luxury; a journey into opulent past lifestyles
15 minutes • Admission Ticket Free
Former Playboy Club
Infamous landmark blending luxury with cultural history; explore the legacy of an entertainment empire.
15 minutes • Admission Ticket Free
East Elm Street
Picturesque street known for its stately homes and tranquil ambiance; a serene escape in the city.
15 minutes • Admission Ticket Free
Highlight
Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Most travelers can participate
This is a private tour/activity. Only your group will participate
Include
Professional local guide services