5 downtown Chicago attractions worth seeing

These five popular spots in the city center are truly worth a visit – crowds or not.

The third biggest city in the USA (population 2.7 million) is known for blues music, hot dogs, and… Prohibition-era gangster wars. But the Windy City also allures visitors with its original architecture (Chicago is the birthplace of the steel skyscraper), top-notch cultural institutions, 26 miles of pedestrian-friendly Lake Michigan waterfront, and diverse neighborhoods.

Some of the major attractions are located in the city center along Michigan Avenue and nearby. Popular, however, does not have to mean “tourist trap” and downtown Chicago proves it. The area is a natural starting point for exploring Chicago and these five spots are likely to please.

Millennium Park

With quiet botanical gardens, unusual public art, and views of skyscrapers and Lake Michigan, Millennium Park is an attractive setting for a walk or picnic. When it opened in 2004, it replaced drab parking lots and railway tracks. It also created a much-needed public space downtown that is enjoyed during the day and after-hours.

Much of Chicago’s nightlife happens away from the business-focused city center. And even though the park has not changed that, it has brought Chicagoans downtown for summer concerts in the outdoor Jay Pritzker Pavilion and in winter for skating in front of the Park Grill restaurant.

On warm days, parents and kids can be seen by the Crown Fountain. Water coming from its two opposing walls (which also project video images) creates a pool where little ones can run and splash.

One of the park’s most unique features is the 33′ feet high, mirror-surfaced Cloud Gate sculpture, affectionately called “the Bean” due to its shape. At any time of the day, you can see people walking around and under it, looking at the reflection of the skyline (and themselves) from a number of angles.

The Art Institute of Chicago Museum

The second largest fine art museum in the USA, the Art Institute has one of the world’s biggest Impressionist and Post-Impressionist collections, including more than 30 paintings by Claude Monet.

When you walk into the second-floor Impressionist gallery, you will immediately see Gustave Caillebotte’s Paris Street; Rainy Day*, a 84 x 109 inches (212 x 276 cm) oil painting, hanging from a partition wall in the middle of the room. You can enjoy the piece either up-close or from benches located across from it.

In the Modern Wing, the museum’s 2009 extension, you can find 20th-century European art, as well as video, photography and design displays. If you need a break from exploring, head to the top-floor Terzo Piano, a 2012 Michelin-recommended restaurant, located in an all-white space reminiscent of the museum’s galleries. It deserves a trip for both food and city views.

For people-watching, have a seat on the grand stairs of the Institute’s Michigan Avenue entrance.

(Admission: $18 adults, $12 students and seniors, children under 14 free; Chicago residents receive $2 off)

The Willis Tower

Don’t call it “Willis” around Chicagoans. The tower is still commonly referred to by its former name, the Sears Tower, and some locals have even fiercely opposed the name change.

The building is the tallest skyscraper in the country and offers 360-degree views of Chicago from the 103rd floor Skydeck. Its recent addition, the Ledge – four glass boxes extending 4.3 feet out  – will let you look down to the street 1,353 feet (412 m) below. An experience not for the faint of heart.

This is one of the city’s most popular attractions and you may have to wait for elevators and a spot on the ledge or by the windows. The expansive views are well-worth the wait, though, and best enjoyed at dusk, when the city lights start to come on.

(Admission: $17.50 adults, $11 youth – ages 3 to 11; bundled packages available)

The John Hancock Center

Another spot for city views is the John Hancock Center in the Streeterville/Gold Coast area, a 20-minute walk north of Millennium Park on Michigan Avenue.

The black wedge-shaped skyscraper is the fourth tallest building in Chicago. The 94th floor Observatory features a cafe and open-air skywalk, but if you’d rather avoid paying cover and have a drink instead, go two floors up to the Signature Lounge.

(Observatory admission: $27 adults, $21.50 youth – ages 3 to 11, children free)

The Water Tower

Two blocks south of the Hancock is the castle-like Water Tower, one of the few buildings that survived the Great Chicago Fire of 1871. You can have a good look at the building from benches in a little square around the tower.

Across the street in the renovated Water Tower Water Works building is the Lookingglass Theatre, winner of the 2011 Regional Tony Award and many Jefferson Awards. It was founded in 1988 by a group of college graduates. One of them was David Schwimmer, who later starred in the TV series Friends and Band of Brothers. The theater specializes in physical performances and incorporating a variety of art forms into its productions.

*included in a traveling exhibition through May 2013

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For more information about the city, read my Chicago Guide.
All photography by Jetting Around

What is your favorite popular attraction, in Chicago or elsewhere? Share your experience in the comments box.