You are here :Home > Major City > Chicago > Guided Tour of Chicago

Chicago Old and New

Explore Chicago, old and new. From famous spaces to historic places discover the wonders of the Windy City as a step-on-guide shows you Chicago’s most fascinating places.

Guided Tour of Chicago Guided Tour of Chicago
Guided Tour of Chicago Guided Tour of Chicago
Guided Tour of Chicago Guided Tour of Chicago
Guided Tour of Chicago Guided Tour of Chicago
Guided Tour of Chicago Guided Tour of Chicago

What to Expect on Your Guided Tour of Chicago's Attractions

During your tour of Chicago, your step-on-guide will give you detailed information on some of Chicago’s most incredible landmarks. Delve into the history behind Chicago’s buildings that date back to the late 1800’s. You will see the renowned sculptures, beautiful parks and iconic places that make Chicago the center of Illinois.


Wondrous Buildings and Structures

Chicago is home to some of America’s most remarkable buildings and structures. It is often considered the birthplace of the skyscraper.  Many buildings date back to the late 1800’s and were built after the Chicago fire of 1871. Sit back and marvel at works by renowned architects such as Ludwig Mies Van Der Rohe, Louis Sullivan and Helmut Jahn as the history of these extraordinary structures unfolds.


Chase One Tower

Once known as the Bank One Building, Chase Tower is situated in the Chicago Loop occupying an entire block. It serves as the headquarters for Chase Bank and Exelon. At 850 ft, the Chase One Tower is the 10th largest skyscraper in Chicago known for its curving features and lively public spaces.


 James R. Thompson Center

Opened in 1985, you’ll find the James R. Thompson Center located in the Chicago Loop. Renowned for its postmodern design, the 17-story, all glass exterior building is occupied by the Illinois State Board of Education and the Illinois House Republican Staff. It has also served as a place in pop culture appearing in several different films.


 Chicago Temple Building

Home to the First United Methodist Church, the 568 ft, 23 floor skyscraper is used for religious and office purposes. Situated on Washington Street, this unusual temple is made of limestone and has distinct detail that makes it stand out from surrounding buildings. Completed in 1923, the Chicago Temple Building remains the tallest church building in the world.


Chicago Board of Trade

The world’s oldest future and options exchange is not to be missed. Established in 1848, the 45-story building not only remains a crucial part of the economy, but also has a fascinating history behind it. Look for the Roman goddess Ceres on top of the Chicago Board of Trade. A 31 ft, faceless statue of Ceres was sculpted by John Storrs. Storrs left the statue faceless because he didn’t believe there would ever be buildings high enough for people to notice the goddess had no face.


Willis Tower

The mere size of the Willis Tower will leave you in owe. Formerly known as the Sears Tower, the 108-story, 1,451 ft building is the tallest in America and the 7th tallest freestanding building in the world.


John Hancock Center

The John Hancock Center, situated on Michigan Avenue, is Chicago’s 4th largest skyscraper at 1,127 ft. Home to offices, restaurants and 700 condominiums, it’s popular among tourists and the ideal location if you’re looking for panoramic views of the city and surrounding area.


 Michigan Avenue Bridge

Proposed in the early 20th century, the Michigan Avenue Bridge, officially called the DuSable Bridge is used as a link between south side and north side parks by cars and pedestrians.  As you cross the historic Chicago landmark look out for the luxurious, 90-story Trump Tower, built by millionaire Donald Trump in 2005.


Harold Washington Library

Bookworms look no further, Harold Washington Library is located just south of the Loop. The library was designed by award winning architectural firm Hammond Beeby Rupert Ainge, Inc., and is stunning both inside and out. Not only is Harold Washington Library the central library of Chicago, but boasts being the biggest public library building in the world.


Federal Reserve Bank of Chicago

As the saying goes, money makes the world go round. Chicago’s Federal Reserve Building is one of the 12 regional reserve banks and along with the Board of Governors, makes up part of the nation’s central bank.


Iconic Places

As America’s 3rd largest city, Chicago is bursting with iconic locations for you to discover, from famous shopping areas, to the homes of the rich and famous.


Magnificent Mile

Running from the Chicago River to Oak Street, the Magnificent Mile is one of Chicago’s renowned locations. The prestigious Mag Mile, located on Michigan Avenue, brings the city to life. While you’ll drive past apartment buildings occupied by stars like Oprah Winfrey, the district is also known as the largest shopping area in Chicago. The street is lined with all shops, restaurants, museums and hotels imaginable.


Culture and Arts

Not only will you get a taste for Chicago’s historic past and the urban city it has become on your Diamond Tours Chicago excursion, but you will also experience the city’s culture and arts scene. From beautiful parks to unique sculptures, Chicago’s cultural art scene is the essence of its personality.



Pablo Picasso’s untitled 50-foot  monumental sculpture located at the Daley Plaza in Chicago’s Loop is just one of the city’s fine works of art. To this day, the subject of this sculpture remains a mystery. The Agora sculpture featuring 106 headless figures is another famous sculpture located in the south end of Grant Park. Designed by Polish sculpture Magdalena Abakanowicz, each figure is 9 ft tall and weighs around 1,800 lbs.  Cloud Gate, often referred to as the, “the bean”, is situated in the heart of AT&T Plaza in Millennium Park. Made by British sculpture Anish Kapoor, it’s a favorite attraction among tourists and can be found in many photos.



You won’t know what’s so special about Chicago’s parks until you see them for yourself. Situated on the north side, Lincoln Park’s trees and grasslands stretch for miles. The Lincoln Park Zoo and Conservatory bring the serenity found in nature to the big city. Grant Park can also be spotted, located in the Loop community,  known as the park where President Obama gave his victory speech in 2008.

Make the Most out of Your Diamond Tours Chicago Excursion

-There will be a lot a of information to take in during your Chicago bus excursion, read ahead about the landmarks you are going to see throughout Chicago to ensure you get the most out of your  Tour.

-The step-on-guide uses a microphone on the motorcoach to point out the great sights you will see throughout Chicago. 

-Don’t forget your camera. There will be plenty of opportunities to capture memories of the Windy City.