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Best Things To Do in Chicago

AOL PICK from our Editors
It’s not hard to find things to do in Chicago. While its many nicknames don’t exactly scream “sophistication” (City of the Big Shoulders, Hog Butcher to the World), this city is inarguably the culture capital of the Midwest, with museums, attractions and restaurants that rival any in New York or D.C. Most of the following attractions are handily located in or near downtown, and the others are well worth traveling a little bit for. A few tips for museum-goers: In peak season, crowds can be formidable, so buy your tickets ahead of time and get there early. And if you’re on a tight budget, take advantage of the free days that just about every one of them offers. Also note that the food options in or around Chicago’s major attractions tend to be sub-par at best; plan to eat elsewhere before or after your sightseeing, so that you don’t end up glumly munching chicken nuggets in a basement cafeteria.  

Margies Candies

Neighborhood: Bucktown
To find one of the top things to do in Chicago, all you have to do is take the Blue Line to the Western stop and look for the huge glowing sign that says “Margie’s Candies.” Despite its name, Margie’s is more famous for its homemade ice cream than its chocolates, and walking into its knickknack-crammed storefront is like visiting your grandma’s house—assuming your grandma served half-gallon sundaes. Founded in 1921 and named after the original owner’s wife, Margie’s has been around long enough to count Al Capone and the Beatles among its customers. You can get a cone to go, but it’s more fun to sit in a booth and eat your ice cream out of a bowl shaped like a clamshell. The people-watching gets especially good after dark (Margie’s stays open till midnight).

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Field Museum

Neighborhood: Museum Campus
Of the 21 million natural, cultural and historical artifacts in the Field’s collection, surely the most popular is Sue, the largest and most complete Tyrannosaurus rex skeleton found to date. Another deliciously scary exhibit here: the stuffed remains of the Tsavo Lions, two wild felines who killed 135 East African railway workers and inspired the movie "The Ghost and the Darkness." And those are just two of the sights in this jam-packed museum, which lets more than a million visitors a year find out what it’s like to walk inside an Egyptian tomb, get a bug’s-eye view of Earth and see scientists prepare specimens for study. In short, this is the place to fulfill all your Indiana Jones fantasies. Get tickets in advance to avoid the lines, and consider stopping in the excellent Shedd Aquarium before or after your visit—it’s right next door.

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Museum of Science and Industry

Neighborhood: Hyde Park
It may not have the jazziest name (“Industry?”), but this museum perched at the southern end of Lake Shore Drive is full of hands-on exhibits and live demonstrations that make subjects like coal mining and worm farming seem downright fascinating. Start with the cool World War II German submarine and then make your way to the baby-chick hatchery, the world’s largest pinball machine and the whispering gallery. If it all sounds a little eclectic, it is, but it's also fun, and that’s the point.

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Wrigley Field Tours

Neighborhood: Downtown
The second-oldest Major League ballpark still in use, Wrigley Field has been the home of the Chicago Cubs since 1916. The Cubs haven’t won—or even reached—a World Series since 1945, but their fans persist in believing their team will prevail again someday. Whether that day ever comes, an afternoon at Wrigley with a bag of peanuts, a cup of beer and a pal or two is a quintessential Chicago experience. If you have your heart set on seeing a game, get your tickets online as far in advance as you can, or you’ll have to take your chances at the ticket windows on game day. On some summer weekends, you can also take a tour of Wrigley that includes the clubhouses and dugouts; call 773-404-CUBS for the tour schedule.

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Second City

Neighborhood: Lincoln Park
Its name may be “Second City,” but this more-than-50-year-old troupe is first in improvisation-based sketch comedy. It hatched the careers of comedy legends both past (Gilda Radner, John Belushi, Chris Farley) and present (Tina Fey, Amy Poehler, Steve Carell). The cabaret seating and full bar make for an intimate evening of laughing yourself silly. Note: Second City shows are so popular that it’s a good idea to get your tickets a month ahead of time if you’re planning on a weekend show; weeknight shows sell out a little less quickly.

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Green Mill Quartet Jam Session

Neighborhood: Uptown
This small jazz club on the North Side was a mobster-patronized speakeasy during Prohibition days; one of Al Capone’s henchmen was even a partial owner for a time. It’s now the place to hear jazz and swing music in Chicago—emphasis on “hear.” While the Mill is a friendly place, it’s also a serious music venue: Don't chat too loudly during a show or you'll get promptly shushed. When the music’s not playing, ask the bartender to show you the scrapbook kept behind the bar, or to point out the trapdoor through which illegal liquor was once delivered. And when the music is playing, well, just sit back and sip your martini.

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Millennium Park

Neighborhood: Downtown
It opened four years behind schedule, but the wait was worth it: Millennium Park has fast become one of Chicagoans’ most beloved green spaces. One of its most famous attractions is Cloud Gate, a 110-ton shiny steel sculpture that most locals affectionately call “the Bean;” the other is the Crown Fountain, which consists of two giant video screens that sandwich a reflecting pool. The screens display the faces of actual Chicagoans, who purse their lips at intervals to “spit” out a stream of water in which kids frolic below. In summer, sprawl on the lawn by the Jay Pritzker Pavilion to hear free concerts; in winter, take a turn on the ice rink or drink hot chocolate in the on-site Park Grill restaurant.

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John Hancock Center

Neighborhood: Downtown
Many visitors hit downtown Chicago with one destination in mind: the Willis (formerly Sears) Tower, the tallest building in the United States. But unless it’s vitally important to you to be 1,451 feet up instead of 1,127, we strongly suggest taking a trip up the John Hancock Center, instead. For one thing, it’s more conveniently located than the Willis Tower; for another, the view is much better; and here you have the option of bypassing the lines for the observatory and just having a drink at the Signature Room on the 95th floor.

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Art Institute of Chicago

Neighborhood: Downtown
Even if you’re not an art buff, you’ll surely recognize many of the works here. The Art Institute’s 260,000-item collection includes icons, such as Edward Hopper’s Nighthawks, Grant Wood’s American Gothic, Georges Seurat's A Sunday Afternoon on the Island of La Grande Jatte, and more Monets than you can shake a stick at. The collection is particularly strong in Impressionist, Post-Impressionist and American works. A Modern wing was added in 2009, making the museum the second-largest in the United States. After you hit the highlights, be sure to check out the Thorne Miniatures, a suite of charming, elaborately wrought dollhouse-sized rooms.

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