A Guide to Some of the Oldest Places in Chicago

Buckingham Fountain<br><i> Photo by Stephen Walker</i>
Buckingham Fountain
Photo by Stephen Walker

Explore the landmarks, hotels, businesses, and institutions that have preserved Chicago’s rich history for generations


By Sophia Schiappa

Timeless Tourist Attractions

Buckingham Fountain

Buckingham Fountain is a monumental Beaux-Arts-style fountain located in Grant Park, Chicago. Dedicated in 1927, it is one of the largest fountains in the world and a defining feature of Chicago’s lakefront landscape. Known for its spectacular water displays and nighttime light shows, it serves as a central landmark symbolizing the city’s brilliance.        

Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States, located in downtown Chicago along Michigan Avenue. Known for its impressive collection of impressionist and post-impressionist art, the Art Institute attracts visitors and locals alike.

Baroque Buildings

The Monadnock Building

Monadnock Building seen from VanBuren Street.

The Monadnock Building is a historic high-rise office building in Chicago, Illinois. It is celebrated as a pivotal example of late 19th-century commercial architecture. Completed in two stages between 1891 and 1893, it embodies the transition from traditional masonry construction to steel-frame skyscraper design, marking a milestone in urban engineering and aesthetics.

Water Tower

The Chicago Water Tower is a historic landmark and one of the few surviving structures from the Great Chicago Fire of 1871. Built in 1869 from yellow Joliet limestone, it stands as a symbol of the city’s resilience and an early example of Gothic Revival civic architecture. Even though the Water Tower is not in use in the municipal water system, the interior serves as an art gallery that is managed directly by the city of Chicago.

Historic Hotels

The Drake Hotel

The Drake Hotel is one of Chicago’s most iconic historic hotels, anchoring the north end of the Magnificent Mile where Michigan Avenue meets Lake Michigan. Since its opening, the hotel has welcomed royalty and celebrities for more than a century while retaining its grand, old-world elegance. Guests are drawn to its ornate architecture, legendary Palm Court afternoon tea, classic Coq d’Or lounge, and unbeatable location steps from Oak Street Beach and the city’s premier shopping and dining.

Palmer House Hilton

The Palmer House Hilton, located in Chicago’s Loop, was built originally in 1871 by Potter Palmer as a wedding gift for his wife, Bertha. Celebrated as North America’s longest continuously operating hotel, key highlights include its grand Gilded Age lobby, the birthplace of the original brownie, and a prime location near Millennium Park.

Oldest Organizations

Chicago Historical Society

The Chicago Board of Trade was founded in 1848 and is the oldest organized futures exchange in the United States. Headquartered in Chicago, Illinois, it sparked standardized futures contracts and became a foundation of modern commodities and financial derivatives trading worldwide.

University Club of Chicago

The University Club of Chicago is a private social and athletic club located in downtown Chicago, Illinois. Established in 1887, it is one of the city’s oldest and most prestigious membership clubs, known for its Collegiate Gothic-style clubhouse and deep ties to Chicago’s cultural and professional communities.

Chicago Yacht Club

Photo courtesy of Chicago Yacht Club

Chicago Yacht Club

The Chicago Yacht Club prides itself on keeping boating accessible to residents of all ages and backgrounds. It stands as one of the oldest and most prestigious yacht clubs in the United States. The club boasts two locations located on Monroe Street and Belmont Avenue, with amenities such as dining, meeting spaces, and social events year-round.

A Bold Business

Central Camera Co.

Central Camera Co. is one of the oldest camera stores in the United States. Opening in 1899, founder Albert Flesch vowed to offer the most up-to-date camera equipment to his customers. A devastating fire completely destroyed the company’s original location on 31 E. Adams St., but it quickly rebuilt after receiving donations and support from members of the local community. After its reopening, Central Camera Co. has remained a hotspot for photography enthusiasts across the Chicago metropolitan area. n

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