Chicago Trip Overview
Discover Chicago’s bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture. Guests will see iconic downtown buildings, hear lesser-known stories from the past, and step inside gorgeous interior spaces.
Additional Info
Duration: 4 to 8 hours
Starts: Chicago, United States
Trip Category: Cultural & Theme Tours >> Cultural Tours
Explore Chicago Promoted Experiences
What to Expect When Visiting Chicago, Illinois, United States
Discover Chicago’s bold character through its beautiful landmarks and fascinating backstories on this thoughtfully designed tour of history, contemporary life and world-famous architecture. Guests will see iconic downtown buildings, hear lesser-known stories from the past, and step inside gorgeous interior spaces.
Itinerary
This is a typical itinerary for this product
Stop At: Chicago, Chicago, Illinois
We’ll start your private “Detour” with a highlights drive. Your professional tour guide will show you a grand view of the magnificent Chicago skyline from Museum Campus. Then you’ll see the city’s varied architectural masterpieces, like historic skyscrapers, grand mansions, and modernist buildings. All the while, your passionate and knowledgeable tour guide will share perspectives on how the city has evolved over history.
Duration: 2 hours
Stop At: Museum Campus, Museum Campus, Chicago, Illinois
Marvel at the spectacular view of downtown Chicago’s world-famous skyline and pose for group photos with the city as your backdrop.
Duration: 15 minutes
Stop At: Printer’s Row, Printer’s Row, Chicago, Illinois
Roll past the iconic Dearborn Station, learn about the industrial history of Chicago, and stop to visit some of the world’s oldest skyscrapers.
Duration: 25 minutes
Pass By: Gold Coast, Gold Coast, Chicago, Illinois
Take a scenic drive through the Gold Coast, an enclave of the rich and powerful for over a century. You’ll spot everything from stately rowhouses to grand mansions, like the residence of the Cardinal Archbishop of Chicago.
Pass By: Lincoln Park, Lincoln Park, Chicago, Illinois
Driving up to the North Side, we’ll share the unexpected origins of Chicago’s famous lakefront park before showing you its beautiful landscapes and prominent attractions, including the Lincoln Park Zoo.
Pass By: Magnificent Mile, Magnificent Mile, Chicago, Illinois
We’ll conclude our Highlights drive by cruising down Michigan Avenue, also known as the Magnificent Mile. Home to some of the most luxurious shopping experience this side of Fifth Avenue as well as some remarkable pieces of history, like the famous Water Tower, and soaring skyscrapers, like the John Hancock Center.
Stop At: Wrigley Building, 410 N Michigan Ave, Chicago, IL 60611-4213
We’ll disembark near the famous Wrigley Building, an iconic skyscraper built just beside the Mag Mile a century ago. From there we’ll take in the spectacular riverfront views, learn about the fascinating layers of history surrounding the DuSable Bridge which carries Michigan Avenue across the Chicago River, and then proceed south for our walking tour.
Duration: 20 minutes
Stop At: Aqua Tower, 225 N Columbus Dr Ste 220, Chicago, IL 60601-7910
We’ll stroll through the Lakeshore East neighborhood, taking in its dense collection of architectural styles, including beloved landmarks like the Carbide and Carbon Building and the Aqua Tower. We’ll pause at carefully chosen vistas to drink in the sights and learn about the differing architectural styles.
Duration: 30 minutes
Stop At: Millennium Park, 201 East Randolph Street, Chicago, IL 60601-6530
We’ll stroll over to Millennium Park and visit the iconic “Bean,” , a work of public art that creates fantastic photo opportunities. We’ll take in surrounding attractions like Pritzker Pavilion and Crown Fountain before continuing.
Duration: 20 minutes
Stop At: Chicago Cultural Center, 78 E Washington St, Chicago, IL 60602-4801
Depending on availability, we’ll take you into one of the most beloved spaces in the city. The Chicago Cultural Center’s magnificent Preston Bradley Hall is a show-stopping space, filled with incredible mosaics, chandeliers, and a soaring stained glass dome.
Duration: 20 minutes
Stop At: Macy’s on State Street, 111 N State St, Chicago, IL 60602-1659
The grand dame of State Street, the historic shopping district of Chicago, the old Marshall Field’s is a wonder. Full of dazzling spaces and countless contributions to local history and culture, this department store amazes visitors more than a century after it opened.
Duration: 15 minutes
Stop At: Daley Bicentennial Plaza, 337 E Randolph Dr, Chicago, IL 60602-1305
The Chicago Civic Center, named for the longtime mayor, is home to the most famously beguiling works of art in the city: the Chicago Picasso. We’ll let you see it from all angles and share some of its fascinating history.
Duration: 15 minutes
Stop At: Chase Tower, 4799 W Madison St, Chicago, IL 60644-3616
We’ll pause in the plaza outside Chase Tower, right in the heart of the Loop, where we can easily see the layers of the city’s architectural history laid out in front of us. Highlights include the dizzying design of Chase Tower, the beautiful simplicity of the Inland Steel Building, and one of the oldest restaurants in the city.
Duration: 15 minutes
Stop At: Marquette Building, 140 S Dearborn St, Chicago, IL 60603-5202
We’ll conclude at the Marquette Building, a skyscraper built in the 1890s. Full of revealing history and directly adjacent to dining, sightseeing, and more, it provides a perfect conclusion to our tour together.
Duration: 15 minutes
