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Art Institute of Chicago -

Founded in 1879, the Art Institute of Chicago is one of the oldest art museums in the world. It's also one of the largest, housing a permanent collection of around 300,000 artworks.

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Browsing the collection -

The Institute is known for its collection of impressionist and post-Impressionist paintings, but is also recognized for its works in the American cannon, pieces that include Edward Hopper's iconic 'Nighthawks' (pictured), created in 1942.

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Favorite pieces -

Vincent van Gogh's 1887 'Self-Portrait' is a hugely popular exhibit. In fact, allow yourself a couple of hours to seek out and admire your own favorite paintings, prints, photographs, sculptures, and decorative art gems. 

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Navy Pier -

One of Chicago's top-rated tourist attractions, Navy Pier opened in 1916 originally as a shipping facility. Today it serves as a boardwalk for an array of leisure facilities and attractions, including shops, restaurants, and bars, an IMAX 3D theater, and a mini amusement park. The Navy Pier Ferris wheel, from where this photograph is taken, affords passengers terrific city-wide views.

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Willis Tower -

Piercing the Chicago skyline is one of America's most iconic buildings, the Willis Tower. Completed in 1974 as the Sears Tower, the needle-like structure reaches a lofty 442 m (1,450 ft) and was once the tallest building in the world. Needless to say, the views from the observation deck are simply breathtaking.

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Willis Tower Skydeck -

One of the highlights of any stay in the "Windy City" is experiencing the Skydeck Ledge, located on the 103rd floor of the Willis Tower. Be one of the more than 1,700 people to visit this dizzying attraction each year, which affords stunning views over the plains of Illinois and across Lake Michigan to Indiana, Michigan, and Wisconsin on a clear day. Or, emerge onto the deck at nightfall and cast your eyes over a sparkling mantle spread out as far as the eye can see.

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Millennium Park -

Chicago's Millennium Park features the centerpiece 'Cloud Gate,' a polished, stainless steel kidney bean-shaped sculpture the surface of which distorts the reflection of Chicago's skyline.

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Crown Fountain -

Millennium Park's Crown Fountain is a clever contemporary take on the traditional spitting gargoyle, with a plume of water ejected from the mouths of projected images of Chicago citizens.

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Field Museum of Natural History -

The largest and most complete Tyrannosaurus rex skeleton yet discovered and affectionately called Sue is among the magnificent collections waiting to be discovered at the the city's Field Museum of Natural History. Sue, by the way, is displayed in the Griffin Halls of Evolving Planet.

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Buckingham Fountain -

The attractive Art Deco-era Buckingham Fountain is more than just a historic water feature. After dark, the carefully choreographed water show is illuminated by lights. Make sure you're in the center of Grant Park at dusk to bag the best spot.

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Museum of Science and Industry -

One of Chicago's most impressive cultural institutions, the Museum of Science and Industry was established in 1933 and is dedicated to the application and promotion of natural laws in technological and industrial development.

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Browsing the Museum of Science and Industry -

Standout exhibits include the German submarine U-505 captured by the Americans during the Second World War, and the command module of Apollo 8. Numbered among the more down-to-earth display are these autographed Michael Jordan Air Jordan Nike Shoes.

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360° Chicago -

The Willis Tower may provide the ultimate bird's-eye views, but for a truly unnerving experience nip up to the near-top of the John Hancock Center (the dark-colored tapered building in this photo, and in fact now known as 875 North Michigan). Why? Read on!

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TILT platform -

This is where you'll find the extraordinary TILT platform, set on the 360° Chicago observation deck on the building's 94th floor. Here, brave visitors are tipped outward at an angle to look straight down 304 m (1,000 ft) from the glass enclosure to the distant streets below.

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Magnificent Mile -

Actually, it's from the TILT platform that you get astonishing views of Michigan Avenue and the Magnificent Mile—Chicago's premier commercial hub and home to a slew of luxury hotels, fine dining restaurants, and upscale retail outlets.

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Wrigley Field -

The city is home to the Chicago Cubs, the iconic baseball team based out of Wrigley Field. Catch a game or take a tour of the famous park, which incidentally is named for chewing gum magnate William Wrigley Jr. (1861–1932). The city's other baseball team, the Chicago White Sox, play out of Guaranteed Rate Field.

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Lincoln Park -

Chicago is blessed with its own incredible green space, Lincoln Park. Encompassing a near 10-km (6 mi) stretch along Lake Michigan, the park features wide-open playing fields, bike trails, and jogging paths. It's even fringed in places by golden patches of sandy beach.

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Lincoln Park Zoo -

The park's big draw, though, is Lincoln Park Zoo. Home to a wonderful variety of animals, including handsome Siberian tigers (who love the snow), it's one of the few zoos in the country that's free to enter.

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Shedd Aquarium -

Expanding the zoological theme is the city's excellent indoor Shedd Aquarium. This is where to admire a wealth of amazing aquatic life, with the beautiful and serene beluga whales (pictured) among the most photographed residents.

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Chicago Riverwalk and Lakefront Trail -

Walking through the city's vibrant hub is the best way to take in the sheer scale of the destination. Follow the wonderful Chicago Riverwalk system that runs parallel to the river, a waterway that's crossed by no less than 18 bridges. Alternatively, tread the Lakefront Trail, which offers beautiful views of the city skyline and Lake Michigan.

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Riverboat cruise -

If walking's not your thing, no problem. Instead, glide through the heart of the city on a riverboat cruise.

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Oriental Institute Museum -

Gazing upon the awesome lamassu, an Assyrian protective deity that originally stood at the palace of Sargon II at Dur-Sharrukin in present-day Iraq and which dates back to 721–705 BCE, is reason enough to spend time in the fabulous Oriental Institute Museum, located on the University of Chicago campus.

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Rookery Building -

Architectural buffs will be inspired by the Rookery Building. Designed by architects Daniel Burnham and John Root in 1888, it's the lobby that truly dazzles, and no wonder. This area of the building was remodeled in 1905 by none other than Frank Lloyd Wright (1867–1959), one of the world's most illustrious and influential architects.

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Chicago Cultural Center -

Another don't-miss example of Chicago architecture is the magnificent Tiffany Dome, found in the ornate Preston Bradley Hall at the Chicago Cultural Center. The 11.5-m (38 ft) glass dome is said to be the largest of its kind in the world.

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Green Mill Jazz Club -

What would Chicago be without jazz? Fans of the music genre should make a pilgrimage to the Green Mill Jazz Club, located on Broadway. Besides its musical heritage, the venue is famous for being a favorite haunt of Al Capone—the gangster's favorite booth is still in the establishment located directly west of the short end of the bar.

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Northerly Island -

Making the effort to reach Northerly Island rewards visitors with the Adler Planetarium, the exhibits of which include the Gemini 12 space capsule. A network of beach and waterfront walks, many of which take in alternative views of the city skyline, can also be explored.

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Chicago Theatre -

Up for a show? Check out what's playing at the Chicago Theatre. This landmark entertainment venue dates back to 1921 and hosts stage plays, magic and comedy shows, and music concerts. Bob Hope, Liza Minnelli, and the Rat Pack number among past performers.

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Museum of Contemporary Art -

The esteemed Museum of Contemporary Art can claim some notable firsts in art history, including hosting Mexican painter Frida Kahlo's inaugural US exhibition. The museum's collection includes works by Andy Warhol and Cindy Sherman. But even if you're not much of an art buff, the building is worth exploring for its cutting-edge interior design, especially the stairwell, an Instagram favorite.

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Route 66 -

Did you know that Route 66, America's "Mother Road," begins its 3,940-km (2,448 mi) run in Chicago? Look for the signs and get your motor runnin'.

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Mount Carmel Cemetery -

Chicago's most infamous son, Al Capone, is buried at Mount Carmel Cemetery, located in the city's Hillside suburb. And the mobster is in good company, resting in peace so to speak with the likes of Sam Giancana, boss of the Chicago outfit, and Frank Nitti, Capone's top henchman.

Sources: (Britannica) (Biography) (Roadtrippers)

See also: Who are the most infamous mobsters and gangsters? 

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