What are the best attractions in Chicago?

Answers from Our Experts (3)

Kevin Aeh

Any Chicagoan will tell you that Millennium Park is a must-visit. During the summer, I'll attend the free concerts at the Jay Pritzker Pavilion at least three or four times. The concerts (everything from jazz to classical and indie to even some electronica) are held on various nights throughout the week and provide the perfect background for a picnic and a bottle of wine. While you're at the park, you have to take a picture of your reflection in front of “The Bean"—Anish Kapoor's massive mirrored Cloud Gate sculpture that resembles a giant kidney bean. And in the winter, you can ice skate in the park.

Some might argue that the top of the John Hancock Building is a bit of a tourist trap, but the views are pretty awesome. I say pop in for a drink in the Signature Lounge on the 96th floor. The drinks are slightly overpriced, but the views are worth it. I've also heard there's a great window view from the women's restroom—but, of course, haven't seen it for myself.

Jaydine Sayer

There are a slew of must-see sites in Chicago, and as a native Chicagoan I think they’re all worth a visit. But if you only have time to check out a few, then put these attractions at the top of your list:

Millennium Park. Located off Michigan Avenue, this large recreational space is much more than a simple park. Take photos at the large reflective sculpture Cloud Gate (known as ‘The Bean’ to locals), stroll through the Lurie Garden and see Frank Gehry’s imposing Jay Pritzker Pavilion. In the summertime you can even catch free concerts here.

The Art Institute of Chicago. Second in size to only the Met in New York, this museum has pieces by famous artists (Picasso, Matisse, Pollock) and a stunning new (opened in 2009) Modern Wing that is worth a visit just to experience the light-filled, beautifully designed space. Tip: Head to Terzo Piano for lunch — it overlooks Millennium Park and is helmed by local celebrity chef Tony Mantuano.

The El. Take a trip through Chicago’s Loop on the elevated trains that run throughout the day. Jump on anywhere in the Loop for a quick circle around downtown, or hop on the Brown line to head up to Lincoln Park and get a look at one of the city’s ritzier hoods. Get off at the Armitage stop to stroll the boutiques that line the avenue.

Lauren Viera

During the warmer months, Millennium Park is a must-visit, both for its stunning architecture and art (you can't miss British sculptor Anish Kapoor's iconic Cloud Gate!), and the massive number of concerts held at the Frank Gehry-designed Jay Pritzker Pavilion. Classical, jazz, indie rock, reggaeton -- it all makes its way here over the summer, and it's all free.

Another wonderful attraction, especially when it's still cold out, is the Lincoln Park Conservatory. No matter the temperature or landscape outside, everything is gorgeous and lush here, and the setting -- in the middle of expansive Lincoln Park -- is lovely, and within reach of downtown. Not to mention, admission is free.

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