One of the most vibrant downtown areas in the world, the Chicago Loop is a must-visit on any trip to the Windy City. And, from Beaux-Arts beauties to modern-design miracles, the buildings in the Loop are a sight to behold. Luckily, the neighborhood is fairly compact, meaning that photographers and architecture buffs can see the highlights on foot.

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Check out another architecturally stunning Chicago neighborhood in Pilsen

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Chicago is home to a fair share of eclectic structures. On the city’s streets, buildings come in every shape and size — so as you explore the Loop, keep an eye out for myriad architectural styles.

Let’s start our tour at the Chicago Architecture Center (111 E. Wacker Drive), which houses a 4,000-building model of the city, as well as oversized scale models of the most famous skyscrapers in Chicago and around the world. Visiting the center is the perfect first stop on our tour — an incredible, extremely interactive way to learn what Chicago architecture is all about.

Just around the corner from the center, on the corner of Wacker and Michigan, you’ll want to check out the view of the Wrigley Building and the Chicago Tribune Tower, both of which are visible on the opposite side of the river. With that piece of the skyline emblazoned in your mind’s eye (and on your camera roll), it’s time to really strike out on our adventure!

On the southwest corner of the intersection, you’ll find the London Guarantee and Accident Building. Completed in 1923, the building incorporates an abundance of classical references into its facade, including Corinthian columns and Roman figures. But the real highlight is the colonnaded cupola on the roof, so crane your neck and take a good, long look at it.

Today, the building has been converted into a luxury hotel called LondonHouse Chicago, and it’s home to a rooftop bar with phenomenal views. Trust us — you’ll want to come back later for drinks!

When you’re ready to continue your tour, head south on Michigan Avenue until you come to Randolph Street, where the Chicago Cultural Center is located on the southwest street corner. Originally a public library, the center was built at the turn of the century in the Beaux-Arts style, and its columns and massive windows are a stunning nod to the era. But this building is just as beautiful on the inside as it is on the outside — so be sure to pop in and see the largest Tiffany stained-glass dome in the world.

Across the street from the cultural center, you’ll find Millennium Park and the iconic Cloud Gate. Better known as “the Bean” for its distinct shape, Cloud Gate is one of the most Instagrammed spots in the city, and it’s easy to see why. Created by an Indian-born British artist, the Bean has been a huge tourist draw since its completion in 2006, so you shouldn’t miss it. Cross the street, take a few pictures, and remember to check out the distorted Chicago skyline reflected in its metallic surface.

As you continue south on Michigan Avenue, you’ll find even more of Chicago’s architectural gems, including the Chicago Athletic Association Building (originally a private club designed to look like the Doge’s Palace in Venice) and the Crown Fountain (a set of 50-foot towers with video projections of faces that look like they’re spitting water onto the pavement). On your way down the street, you might even spot a highway marker indicating the official beginning of Historic Route 66.

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Between Monroe Street and Jackson Boulevard, the Art Institute of Chicago stands as another important landmark. Originally built for the Columbian Exposition of 1893, the Art Institute features symmetrical wings, Greco-Roman motifs, and a set of bronze lions outside its main entrance. Since the institute first opened, it has constructed eight additional buildings to house its growing collection, but the main structure remains the most recognizable.

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When you’re ready to move on, continue south for another block, then head west on Van Buren Street. Where Van Buren intersects State Street, you’ll find the Harold Washington Library. This building’s design was the winning one in a competition to replace the city’s old public library (then the Cultural Center), and much of the exterior is decorated with owls to symbolize that the structure is a place of wisdom. The library’s main entrance is located at 400 S. State Street, and if you go inside, make your way to the ninth floor and check out the Winter Garden — a glass-roofed atrium that many esteem as Chicago’s best-kept secret.

After your library visit, go back to Van Buren and walk westward until you come to Dearborn Street. Head north, and keep an eye out for the Monadnock Building on your left. This structure has an interesting history, since it was built in separate stages by two different firms. The newer, southern half dates to 1893, revolutionary in its use of a steel framework to support the external walls. By contrast, the northern half (completed in 1891) is entirely comprised of bricks, each one supporting the weight above it. In some places, the northern walls are six feet thick, so the structural differences between the two halves are fairly easy to spot. The Monadnock is significant because it provides a visual example of an important transition in American architecture.

By now, you should be on Jackson Boulevard again. Head west until you reach the Chicago Board of Trade Building (141 W. Jackson), a hard-to-miss, 45-story skyscraper. And its location — opposite a narrow street of towering buildings, nicknamed “the Canyon” — makes this Art Deco structure even more impressive. Its vertical lines, pyramidal roof, and colossal statues give it an unmistakable 1920s feel, so be sure to snap a few photos before moving on.

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Continue west on Jackson Boulevard and then head north on Wacker Drive. From here, you’ll come face to face with the Willis Tower — a giant skyscraper with a maximum height of 1,729 feet (527 meters). For about 25 years, it was the tallest building in the world, and although it has since lost that distinction, it’s still the tallest structure in Chicago. The tower is actually made up of nine square tubes that reach four separate heights, giving the building an unusual shape and helping it withstand strong winds. Today, the Willis Tower is extremely popular with tourists, thanks to the glass balconies jutting out of the building 1,353 feet (412 meters) above street level.

Head to the Willis Tower’s Skydeck if you dare, and peer down at the tiny streets, cars, and pedestrians below. It’s a dizzying — yet thrilling — way to see the skyline and spot other architectural beauties that you might want to visit later.

That concludes our tour of the Loop! Although this neighborhood showcases some of the most varied architecture in Chicago, the Windy City offers lots more to see. Keep exploring, and let us know what you find.

Cover photo by Sawyer Bengtson

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Whitney Brown
Whitney Brown is a recent journalism graduate and travel writer based in Utah. She has lived in France and Ireland, and she's always planning her next big adventure. In addition to her passion for travel, Whitney loves archaeology, photography and floral design.