What to Include in the Chicago Architectural Tour: Chicago Itineraries 101

July 28, 2022
Liz Arnold

Among the many highlights of the Windy City, few are more iconic than its extraordinary wealth of architectural masterpieces. Chicago features one of the largest and most diverse collections of buildings designed by some of the most celebrated American architects, such as William Le Baron, Frank Lloyd Wright, Louis Sullivan, and Mies Van der Rohe, resulting in the iconic skyline we can admire today.

Architectural foundation tours are a must for any visitor. Besides, you can opt for Chicago group transportation, so the tour is pleasant and accessible to all your guests regardless of age and physical abilities. Here are some of the highlights of all Chicago architectural tours.

The Chicago Loop

Chicago’s business district is affectionately known as “The Loop”. It owes its moniker to the two cable car lines built in 1882 that shared a loop bounded by Van Buren Street, Wabash Avenue, Wells Street, and Lake Street. 

The Chicago Loop is home to some of the most famous Chicago landmarks and is a must in all Chicago itineraries. Some of the most notable buildings include the Chicago Board of Trade Building and the Willis Tower (formerly known as the Sears Tower), which was once the world’s tallest building. Since the most exciting structures are spread out, you may want to organize an architectural bus tour of Chicago.

Chicago Lakefront

All the best Chicago architecture tours will take time to explore the scenic Chicago lakefront. Facing the turquoise blue water of Lake Michigan, the lakefront area features stunning views of the Chicago skyline and is primarily used for recreational purposes. From multi-use trails and white sanded beaches to concert venues and welcoming parks, the lakefront district is an essential part of any Chicagoan’s life and visitors’ favorite stop. 

It features spectacular displays of outdoor sculptures created by the likes of Pablo Picasso, Joan Miró, Henry Moore, Marc Chagall, Magdalena Abakanowicz, and Alexander Calder, as well as Anish Kapoor’s iconic “Cloud Gate”, along with museums as breathtaking outside as they are inside.

Carbide and Carbon Building

Your guests may already have checked into the Carbide and Carbon Building since it was converted into the Hard Rock Hotel in 2004. Designed by the Burnham Brothers and built in 1929, it is a masterpiece of the Art Deco style and will not fail to wow your visitors on any Chicago building tours. According to the local legend, the architects pulled their inspiration from a Champagne bottle, using black granite with black marble and bronze trim as the exterior base, dark green and gold terra cotta as the central shaft, and an exquisite 24k gold-covered tapered cap.

The Rookery

All Chicago architectural tours should include a stop at this spectacular location, completed by architects Daniel Burnham and John Wellborn Root of Burnham and Root in 1888. In the wake of the Great Chicago fire of 1871, architects competed nationwide, mixing modern building techniques, such as fireproofing, elevators, and plate glass, together with Old-World-inspired aesthetics. 

The Rookery is a prime example of what is now known as the Chicago school of commercial architecture. In addition, revered architect Frank Lloyd Wright himself redesigned the sky-lit, two-story lobby in 1905, aptly known as the Light Court. This celebrated landmark has been part of the National Registry of Historic Places since 1970 and is now home to prestigious businesses and offices.

best chicago architecture tour

Chicago SkyDeck

If you have caught a glimpse of former Chicago visitors suspended into clear observation boxes offering vertiginous views of the city below on social media, you have already met guests of the Chicago SkyDeck. Displaying breathtaking panoramas spanning up to four states on a clear day, the Chicago Sky Desk stands 1,353 feet off the ground and is not for the faint of hearts. 

However, it is undoubtedly a highlight for any first-time or returning visitors and a must-have for the best Chicago architecture tour. Make sure you include this unique experience when designing Chicago itineraries for your guests.

Chicago Board of Trade

Until it was dethroned by the Richard J. Daley Center in 1967, the Chicago Board of Trade once stood as the tallest building in the Windy City since its inception in 1930. Erected at 44-story and 604 feet tall, this Art Deco behemoth features gray Indiana limestone and a massive, 31-feet statue of the Roman goddess of grain Ceres dominating it. It also displays impressive murals on the trading floor. It is an especially spectacular stop on Chicago architectural tours by night since its upwardly-lit floodlights further emphasize the structure's vertical elements.


Chicago has nothing to envy even for the most spectacular architecture tours in Europe. The Windy City features a unique and breathtaking display of examples of American entrepreneurial spirit and imagination in the form of vertiginous skyscrapers of all shapes. Hiring a Chicago charter bus company is the most comfortable and accessible way to explore this unique setting. If you are considering including an architectural bus tour of Chicago as part of the entertainment for your personal or business guests, do not hesitate to contact us for a personalized quote for your bus tour.

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Illinois Areas We Provide Charter Bus Rentals For

We serve businesses, organizations, and private parties across Chicago and surrounding areas, from Glencoe and Northbrook to Joilet, Rosemont, Lake Forest, and beyond.

Discover the vibrant charm of Arlington Heights, where modern meets tradition. Indulge in diverse culinary delights, explore renowned museums, and cheer for your favorite team at Arlington International Racecourse. Unforgettable memories await your group adventure!

Experience the magic of Aurora, where history intersects with the present. Marvel at the grand architecture, enjoy riveting performances at the Paramount Theatre, and engage in vibrant local festivals. Your group journey begins here!

Embark on an adventure in Bolingbrook! Relish family fun at The Promenade, revel in the natural beauty of Hidden Lakes Historic Trout Farm, or tee off at Boughton Ridge Golf Course. Explore Bolingbrook today!

Cicero awaits, blending historic charm with urban convenience. Explore the bustling local markets, savor authentic Mexican cuisine, and immerse in the lively local festivals. Cicero - a treasure trove of unique experiences!

Unearth the gem that is Des Plaines! Witness the birthplace of McDonald’s, relax by the tranquil Lake Opeka, and learn something new at the Des Plaines History Center. The perfect destination for your group!

Explore Elmhurst, where tradition and innovation intertwine. Visit the iconic Elmhurst Art Museum, shop in charming boutiques, and taste unique brews at local breweries. Get ready for your next bus trip to Elmhurst!

Discover Elgin, where the Fox River brings people together. Visit the Grand Victoria Casino, immerse yourself in Elgin Symphony Orchestra's melodies, and engage with nature at the Hawthorne Hill Nature Center.

Evanston is ready for you with its lakeside charm and vibrant intellectual life. Stroll around Northwestern University's campus, enjoy the arts at Noyes Cultural Arts Center, or unwind at Evanston’s scenic beaches. A must-visit destination for any group!

Hoffman Estates

Hoffman Estates is an enticing destination for your next trip. Infinity Transportation’s impeccable charter buses, including deluxe coaches and minibus rentals, serve both small groups and larger parties.

Mount Prospect

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Experience Naperville, where modern living meets rich history. Visit the iconic Naperville Riverwalk, explore interactive exhibits at the DuPage Children's Museum, or try shopping downtown. Grab a charter and make your memories here!

Welcome to Northbrook, a haven of natural beauty and recreation. Experience the thrill of speed at the velodrome, explore the scenic Botanic Garden, or shop at Northbrook Court. Your adventure starts here!

Oak Lawn

Embark on a delightful journey through Oak Lawn, IL, with Infinity Transportation's diverse charter bus services. Proudly serving major markets, our luxury coaches and minibus rentals are perfect for small groups and larger gatherings.

Orland Park

Discover a wide array of bus rental options in Orland Park with Infinity Transportation. Our fleet of charter buses is designed to accommodate groups of all sizes and cater to various travel needs.


With a keen understanding of Palatine and its surroundings, our bus rental services are tailored to offer the ultimate in local transportation excellence. Our charter buses and motorcoaches are equipped for all your travel needs, ensuring you reach your destination safely and in comfort.

Dive into an urban playground teeming with shopping, entertainment, and cultural experiences. The possibilities for your group are endless, from the renowned Woodfield Mall to the Schaumburg Convention Center. Schaumburg invites you to indulge in excitement and adventure.


Experience the convenience and reliability of our bus rental services in Skokie, providing you with ample luggage space and essential amenities for a comfortable journey regardless of your destination.

Tinley Park

Tinley Park is a gem waiting to be explored. With our charter bus and party bus rental options, your group can travel comfortably and conveniently to various attractions and events in this vibrant city.

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Unveil the splendor of Waukegan, a harbor city with a rich cultural tapestry. Visit the Genesee Theatre, enjoy Lake Michigan's serene vistas, or dive into history at the local museums. Waukegan is ready for your next bus trip!


Experience the premium transportation services tailored for Wheaton, IL, by Infinity Transportation.

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