The Marquette Building was one of the most profitable skyscrapers built in Chicago during the 19th-century building boom. This historic landmark stands as an ideal example of a speculative commercial office building. It was created as a collection of first class office spaces whose primary purpose was to fatten the pockets of real estate investors taking a gamble on an up-and-coming urban center.

When completed, the Rookery was thought to be the largest and finest office building in the United States. Located at the corner of LaSalle and Adams, the Rookery is one of Chicago’s most elegant buildings and a star of the LaSalle Street financial corridor.

The Palmer House, is a historic Hilton Hotel and the longest continuously operating hotel in North America, located in Chicago's Loop district! It was the city's first hotel with elevators, and the first hotel with electric light bulbs and telephones in the guest rooms.

The Sullivan Center better known as the former home of the Carson Pirie Scott store, is one of the most representative works of the famous Chicago School and one of the most important in the history of tall buildings. Built between 1899-1903, it has been used for retail trade throughout its life and was declared a milestone of Chicago in 1975.

The Chicago Athletic Association hotel is located in Chicago's loop district. It occupies an 11-story Venetian Gothic building designed by architect Henry Ives Cobb and completed in 1893. From its construction all the way until 2007, it functioned as a private club for wealthy Chicagoans. This rich and exclusive history is preserved in the hotel’s modern refurbishment, as the renovators preserved the majority of the structure’s bells and whistles. This means the interior space today remains dominated by an assortment of ornate paneling, elaborate molding, and beautiful trims. Intricate details are everywhere here, yet the space still manages to feel fresh and modern. Nestled directly across the street from Millennium Park, the boutique hotel is housed within a Venetian Gothic building that sports modern amenities infused with grand historic details, lauded restaurants, ballrooms with jaw-dropping Lake Michigan views, and cozy pubs where libations and conversation flow freely.

The Chicago Cultural Center is one of the city’s most popular attractions and the cultural heart of the downtown Loop neighborhood. Taking up an entire city block, the stunning landmark building is home to the world’s largest Tiffany stained glass dome and presents more than 700 humanities programs a year — and many of them are free and open to the public. Spend hours admiring the architectural splendor of this Chicago gem or just stop in for a quick dose of culture

One of Chicago’s most iconic buildings is the Tribune Tower. Despite rising only 36 stories, the tower has helped set Chicago apart as a living architectural museum. Its soaring Gothic spires and shrine-like lobby, complete with inspirational quotes, are by now iconic identifiers of the city and make it a thoroughly Chicago building.

The Wrigley Building is one of downtown Chicago’s most recognized architectural icons, dating to the 1920s.Even though the building was ornamented with French Renaissance elements, the most prominent feature of the structure is the clock tower. This reaches a height of 130 meters (425 feet) which effectively makes it a magnificent skyscraper as well.