The Getaway
Some of the Best Things to Do in Chicago

Located along the southwest shore of Lake Michigan, Chicago is a vibrant city that's full of life. The city's famous for its beautiful skyline, its deep-dish pizza, and an array of important landmarks. Chicago boasts warm, comfortable weather in the summertime, and while winters are chilly, the snowfall makes for a picturesque scene and plenty of fun winter activities. Whether you're local or just passing through, Chi-town has plenty of things to do that appeal to just about every taste.


01 Wrigley Field

Located on Chicago's north side, Wrigley Field is a Major League Baseball field that's home to the Chicago Cubs. It's the second-oldest active ballpark in the United States. Visitors can take in a game, or if you're visiting in the off-season, the stadium offers 90-minute behind-the-scenes tours that give you the opportunity to learn first-hand about its history.


02 Chicago architecture cruise

Chicago is famous for its great architecture. The city is home to buildings like the Willis Tower (formerly Sears Tower), Navy Pier, and the John Hancock Building. Visitors can enjoy taking in the best architecture Chicago has to offer on the Chicago Architecture Cruise, a one-hour trip down the Chicago River that passes by the city's most famous buildings.


03 Frank Lloyd Wright's Robie House

Designed for Frederick Robie by Frank Lloyd Wright and built in 1906, this house was the first to be recognized as prairie style. The house features long, rectangular design and 20-foot cantilevered roof shades with art-glass windows. It's been declared a National Historic Landmark, and today, it's open to the public for guided tours.


04 Italian beef sandwiches

Chicago may be famous for its pizza, but the Italian beef is at the center of the city's culinary treasures. The sandwich, which has been a staple in Chicago since the 1930s, features thinly-sliced roast beef that's been simmered in au jus and served on a long French roll with bell peppers. You can find these sandwiches just about anywhere in the city.


05 The Green Mill

The Green Mill is Chicago's ultimate destination for jazz music. This lounge is thought to be the oldest jazz club in the country and, during the prohibition era, had ties to Al Capone. It's hosted many greats on its stage, including Billie Holiday, Franz Jackson, and Wilbur Campbell. If you're a fan of jazz and you're over 21, make sure to pay The Green Mill a visit while you're in the city.


06 Rush Street

Rush Street is a great place to take in upscale. It's home to an array of highly-rated hotels, bars, restaurants, and nightclubs. This one-way street has been an important part of Chicago since its incorporation in 1930, and in addition to being a fun place to stay and eat, it's also famed for hosting the residences of some of the city's most important habitats, including Chicago's first mayor.


07 Steppenwolf Theatre

Perhaps the most famous attraction in Chicago's arts scene, Steppenwolf Theatre has housed many well-known productions, including August: Osage County and The Grapes of Wrath. As of 2023, the theatre's performances had amassed 12 Tony Awards and a National Medal of Arts. Actors who've graced the theatre's stage include John Malkovich, Gary Sinise, and Laurie Metcalf.


08 The Second City Theatre

If you love to laugh, and who doesn't, the Second City Theatre in Chicago is a must-see. This improv theatre and school of comedy has had plenty of famous comedians perform on its stage and study under its leaders. That includes Saturday Night Live alum Tim Meadows and Chris Farley, as well as actors Harold Ramis and Alan Arkin.


09 Murals on 16th St.

Located in Pilsen in the city's lower west side, the 16th Street Murals are a sight to be seen for art connoisseurs. Running along Halsted Street West to Western Avenue, these bold, bright murals cover a two-mile stretch. The murals are painted by local street artists, including Sam Kirk, Amuse, and Chris Silva, as well as international artists, such as Roa and Sheryo.


10 Dine at 2D Restaurant

2D Restaurant offers a unique dining experience. The restaurant serves Asian gourmet cuisine, including Japanese mochi donuts and Taiwanese chicken sandwiches, in a restaurant that's decorated from wall to wall with monochrome comic book scenes. 2D Restaurant is owned and operated by a husband and wife team and was designed in partnership with local artist Mia Larson. The walls are designed to make for fun photo ops, with different scenes and props depicted throughout the restaurant.


11 Willis Tower

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Once the tallest skyscraper in the world, when it was famously known as the Sears Tower, Willis Tower is a major Chicago attraction. Completed in 1973, Willis Tower has 110 stories. Taking an elevator to the observation deck is a Chicago rite of passage. When you get to the top, you'll have a majestic view of the city. Do your best to schedule this stop for a clear day; you'll have a great view of the lake shore and other breathtaking urban sights.


12 Art Institute of Chicago

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The Art Institute is a world-class art museum and one of the oldest in the country. Roughly 1.5 million people visit this museum, and the more than 300,000 pieces of art it owns, each year. The collections range from ancient to modern. While there, make sure to witness some of the masterpieces created by El Greco, Rembrandt, Renoir, Manet, Picasso, and Gauguin. Don't forget to pose for a selfie outside the museum with one of the famous lion statues.


13 Navy Pier

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Navy Pier is an exciting attraction for people of all ages. The pier boasts famous views of Lake Michigan, but it's also home to amusement park rides, an amazing concert venue, and the celebrated Chicago Shakespeare Theater. If you're visiting the Windy City with kids, be sure to visit the popular Children's Museum, too.


14 Field Museum of Natural History

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Founded in 1893, the Field Museum of Natural History is home to the world's most complete T. Rex skeleton and a plethora of other impressive exhibits. One of the largest museums in the world, the Field Museum is easily one of Chicago's most culturally important attractions. When visiting, you'll want to peruse some of the most popular permanent exhibits like the gem and mineral collection and the famed Animal Halls. The museum also features temporary attractions that draw throngs of visitors from near and far. The museum gift shop is the perfect place to find a souvenir of your visit to the city.


15 The Neighborhoods

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When visiting Chicago, be sure to set aside time to visit some of its culturally rich neighborhoods, such as Greek Town and Chinatown. Like many other major cities, Chicago attracted large populations of immigrants who settled in neighborhoods with others of the same ethnicity. These sections of the city became cultural hubs and still feature amazing restaurants, shops, and galleries.


16 Shedd Aquarium

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Built in 1930, the Shedd Aquarium is situated on Chicago's Museum Campus, right on the lake. For a time, this historic aquarium was one of the world's largest. Today, it has been expanded and renovated to feature a dazzling array of special collections. When you visit, expect to see black-tip reef sharks, piranhas, stingrays, green sea turtles, dolphins, beluga whales, and penguins. No matter your age, you won't be disappointed with the aquarium's many creatures.


17 The Magnificent Mile

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The Magnificent Mile is home to Chicago's leading shopping district. Located downtown on Michigan Ave., this decadent boulevard hosts world-class shops and stores. Water Tower Place is the highlight of the Magnificent Mile. You'll find a mall's worth of shops that include The Lego Store and American Girl. There are also many cafes and restaurants scattered throughout the area.


18 Deep-dish pizza

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If you don't believe that pizza alone is worthy enough to be a Chicago attraction, then make your way to a famed pizza parlor such as Giordano's or Gino's East, both located just off the Magnificent Mile. Deep dish pizza is one of Chicago's culinary claims to fame. Although you can find thin crust throughout the city too, this classic style put this city on the pizza map.


19 The Oriental Institute

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Located on the University of Chicago campus, the Oriental Institute houses antiquities of the ancient world, particularly the Near East. Its famous artifacts come from ancient cities like Babylon, Ur, and Persepolis. It features collections of archaeological relics from ancient Egypt, Persia, Israel, Assyria, Iran, and Iraq. The Oriental Institute was founded in 1919 and has since become one of the world's foremost authorities on Ancient Near East cultures. If you have time, extend your stay to browse the great bookstores located on the campus.


20 Millennium Park

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The recently renovated Millennium Park is popular with tourists and city residents alike. Part of Grant Park, Millennium Park is home to the celebrated Cloud Gate sculpture as well as the Lurie Garden and Jay Pritzker Pavilion, a popular concert venue. Events are often held in and around the park during the warm season. It's also a great place to relax with friends and enjoy some people-watching.


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