Private Guided Chicago City Tour

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.

City: Chicago

Sun 23 Feb

Other dates

You can choose the date already on the booking website

Starting at $425.00

Make a reservation

Sun 23 Feb

Starting at $425.00

Make a reservation

New York City Tours

Unique Activities (21) Transfers & Transportation (103) Tours, Sightseeing & Cruises (113) Entry Tickets (47) Sporting Events (1) Good for Small Groups (6) Seasonal & Holiday Tours (41) Walking Tours (697) Outdoor Activities (20) Limitied Availability Tours (6) LGBT Friendly Tours (4) Family-friendly Activities (7) Solo Travelers' Tours (147) Food & Drinks (27) Travelers recommend (73) Good for Groups (8) Top Activities (18) Guided Audio Tours (3) Art, Culture & History (135) Attractions to explore (38)

What's Included

Private transportation

Professional local guide

Additional Info

Wheelchair accessible
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
Face masks required for travellers in public areas
Face masks required for guides in public areas
Hand sanitiser available to travellers and staff
Social distancing enforced throughout experience
Regularly sanitised high-traffic areas
Gear/equipment sanitised between use
Transportation vehicles regularly sanitised
Guides required to regularly wash hands
Contactless payments for gratuities and add-ons
Only guides who have received a full Covid-19 vaccination will operate in-person tours.

What To Expect

Chicago

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.

Museum Campus

Marvel at the spectacular view of downtown Chicago's world-famous skyline and pose for group photos with the city as your backdrop.

Printer's Row

Roll past the iconic Dearborn Station, learn about the industrial history of Chicago, and stop to visit some of the world's oldest skyscrapers.

Gold Coast

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.

Lincoln Park

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.

Magnificent Mile

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.

Wrigley Building

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.

Aqua Tower

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.

Millennium Park

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.

Chicago Cultural Center

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.

Macy's on State Street

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.

Daley Bicentennial Plaza

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.

Chase Tower

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.

Marquette Building

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.

Show 11 more stops

Cancellation Policy

All sales are final. No refund is available for cancellations.

Traveler Photos

Reviews (1)

suedH6644HQ

Nov 2021

This tour was hands down, the best tour I’ve been on that shows so many different aspects of the city. We saw so many different areas and really cool interior as well as exterior architecture. When our guide said she had previously worked with Rick Steve’s, it all made sense. 10/10 I would highly recommend!