Skip the crowds this is a private tour for your group only! 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.
Iconic skyscraper offering breathtaking Lake Michigan views; a marvel of modern architecture.
Historic residence of the famed architect; a glimpse into Chicago's architectural heritage.
Elegant hotel embodying Chicago's rich history and sophistication; a stay worth experiencing
Prestigious street lined with architectural gems; a walk through Chicago's elite history.
Masterpiece showcasing the collaboration between Adler, Sullivan, and Wright; a cornerstone of architectural innovation.
Grandiose mansion reflecting Chicago's Gilded Age luxury; a journey into opulent past lifestyles
Infamous landmark blending luxury with cultural history; explore the legacy of an entertainment empire.
Picturesque street known for its stately homes and tranquil ambiance; a serene escape in the city.
We will meet outside the 1150 Lake Shore Drive Building.
Chicago is a vibrant city known for its stunning architecture, rich cultural heritage, and world-class cuisine. Situated along the shores of Lake Michigan, it offers a unique blend of urban excitement and natural beauty, making it a must-visit destination for travelers from around the globe.
Millennium Park is a famous public park in downtown Chicago, known for its modern art and architecture. It's home to the iconic Cloud Gate sculpture, also known as 'The Bean'.
One of the oldest and largest art museums in the United States, the Art Institute of Chicago houses an impressive collection of artworks from around the world.
Located on the 103rd floor of the Willis Tower, Skydeck Chicago offers breathtaking views of the city and Lake Michigan. Visitors can step out onto The Ledge, a glass balcony extending out from the building.
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
A thick, buttery crust filled with layers of cheese, toppings, and tomato sauce. It's a Chicago classic and a must-try for pizza lovers.
A steamed or grilled all-beef hot dog topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato wedges, pickled sport peppers, and a dash of celery salt, all served on a poppy seed bun.
Thinly sliced beef cooked in its own juices and served on an Italian roll. It's typically dipped in the juices and topped with sweet or hot peppers.
A sweet and savory snack made with caramel and cheese-flavored popcorn, often sold in colorful boxes at street corners and ballgames.
This is the best time to visit Chicago for outdoor activities, festivals, and sightseeing. The weather is warm and pleasant, making it ideal for exploring the city's parks and attractions.
United States Dollar (USD)
Central Time Zone (CT) (GMT-6)
120VV, 60HzHz
Chicago is generally safe for tourists, but visitors should be aware of their surroundings and take precautions to protect themselves and their belongings. Some areas of the city have higher crime rates, and visitors should research their destinations before traveling.
Union Station, Ogilvie Transportation Center
Greyhound Station, Megabus Terminal
The 'L' is a convenient and affordable way to get around Chicago. It consists of eight color-coded lines.
Available • Apps: Uber, Lyft
Car, Bike, Scooter
Navy Pier is a 3,300-foot-long pier on the Chicago shoreline of Lake Michigan. It offers a variety of attractions, including shops, restaurants, and rides.
Wrigley Field is a historic baseball park located on the North Side of Chicago. It's home to the Chicago Cubs and offers a unique atmosphere for sports fans.
The Museum Campus is a 57-acre park located on the southern tip of Grant Park in Chicago. It's home to several world-class museums, including the Field Museum, the Shedd Aquarium, and the Adler Planetarium.
Price varies by option