Chicago jam-packs some of America’s most significant architectural masterpieces. From William Le Baron Jenny to Daniel Burnham and Mies Van Der Rohe, many of the architectural greats have left their mark on the Windy City, making it a veritable wonderland for modern architecture fans.

With so many iconic buildings spread out over Chicago’s 234 mi² surface, renting a charter bus in Chicago for your group’s architectural visit will provide you with the flexibility of creating your own itinerary. Whether you’re an urban-planning or architecture buff, here is how we suggest you plan your bus tour of Chicago’s most Iconic buildings in the Downtown area.

Sight-seeing in the Chicago Loop

Rent a charter bus and visit Chicago's most iconic architecture.
The Chicago Loop is one of the best places to observe American modern architecture. Photo courtesy of @yazbadri via Twenty20

The Loop is Chicago’s central business district, and gains it’s moniker from the cable cart system that looped around the area in the late 1800s. Its blurred boundaries encompass many famous landmarks making it one of the most famous areas in the city, and definitely where first-timers should spend the majority of their visiting time.

While sightseeing in the loop is perfectly manageable on foot, groups with a limited amount of time might choose to travel between points of interest by bus. 

If you’re planning a bus tour of Chicago’s financial district, hop off and get a closer look of the following landmarks:

Chicago Sky Deck at the Willis Tower

Plan a tour of Chicago's most iconic architecture with a charter bus rental.
The Sky Deck offers a stunning view of Chicago. Photo courtesy of @mattspencerdavey via Twenty20
  • Visit Time: 1 to 1.5 hours (depending on lines!)
  • Sky Deck Admission: $24 for ages 12 and up, $16 for ages 3 to 11

Built in 1973, The Willis Tower (also known as the Sears tower) is the second tallest building in the Western Hemisphere. The beautifully designed building’s main appeal is the glass-floor boxes protruding from it’s facade at 1,353 feet off the ground, from which visitors can observe a spectacular view of Chicago. While it provides a worthy visit for first-timers and urban-planning buffs, height-fearing visitors might want to skip the $24 entrance to the Sky Deck and move on to more earthen structures.

The Carbide and Carbon Building Lobby

Charter a bus and visit Chicago's downtown architecture.
The gilded tower on the Carbon & Carbide building makes it look like a bottle of champagne. Photo courtesy of @sytphotos via Twenty20

Visit Time: 15-20 minutes

The Carbide and Carbon Building, a gleaming reminder of Chicago’s most opulent decade, was built in 1929 when Americans still took their architectural cues from the old continent. The building’s facade is made of polished black granite and dark-green terracotta with gold-leaf Art Deco accents, and now houses the Hard Rock Hotel.

The building’s tapered cap is covered in 24K gold, making it look like a champagne bottle. Despite how this Art Deco masterpiece looks on the Chicago skyline, it’s lobby is what takes the cake in terms of lavish extravagance, so try to sneak a peek inside!

The Rookery Light Court

Charter a bus and take a tour of Chicago's iconic architecture.
The Rookery’s Lobby is one of Frank Lloyd Wright’s most iconic designs. Photo courtesy of @ginarossi via Twenty20.

One of the oldest standing high-rises in Chicago, the Rookery, was built during the architectural boom that ignited from the ashes of the Great Chicago Fire.  While architects, Burnham and Root’s, created techniques and eclectic motifs that can be observed from the outside, it’s the Light Court designed by Frank Lloyd Wright that brings lovers of modern architecture flocking to it’s gilded doors. Hop off your Chicago bus tour for 15 minutes to take either a picture of this architectural icon, or invest in a $10 tour by the Frank Lloyd Wright Trust.

The Chicago Board of Trade

Charter a bus and tour Chicago's iconic architecture.
The Chicago Board of Trade carves an impressive shape on the Chicago skyline. Photo courtesy of @photomintie via Twenty20

Before being dethroned by the Richard J. Daley center in 1967, the Chicago Board of Trade was the highest building in Chicago, and is still known for its large trading floors. Topped by an iconic sculpture of the Roman goddess Ceres, the art deco behemoth stands as if it was a temple to capitalism. Ironically, construction on the Chicago Board of Trade ended in 1930, right at the beginning of the great depression.

The Sullivan Center

Charter a bus and tour Chicago's downtown architecture.
The Sullivan Center is trimmed with Art Deco ornamentation.

The Sullivan Center was built in 1899, and is situated on State Street, a commercial hub known as the birthplace of the modern department store. The building’s white terracotta facade reveals its underlying structure, and is trimmed with Sullivans famed organic ornaments. A stop at this famous department store and office building is not only a treat for Louis Sullivan enthusiasts, but also the perfect occasion to indulge in a little shopping.

Get a Full View of Chicago’s Iconic Lakefront

Rent a bus and plan your tour of Chicago's architecture.
A boat tour is one of the best ways to get a view of the architectural masterpieces lining Chicago’s waterfront.
  • Tour time: 1h15
  • Shoreline sightseeing: $37 to $43 for aduts, and $19 to $24 for Children  (Free for children under 2)

While the Chicago waterfront can be seen on-foot from the Riverfront, the best way to see it is undoubtedly by boat! A chicago architecture boat tour will allow you to fully appreciate the density of landmarks in Chicago’s city center.

Take a Stroll in Millenial Park

Charter a bus and take a tour of Chicago's iconic architecture.
Instagram or you weren’t there! No trip to Chicago is complete without a stroll in Millenial park. Photo courtesy of @amanda.arner via Twenty20.

Of course, no visit of downtown Chicago would be complete without the mandatory tourist snapshot of the Cloud Gate. Visitors can learn all about the history, architecture, and art of the park by talking with one of the volunteers from Millenial Park Greeters.

If you’re planning a tour of Chicago’s iconic downtown architecture, make sure to check out our guide on renting a bus to figure out which bus type is best for your group!