Fortunately for visitors, many of the most popular Chicago attractions are concentrated downtown and within a scenic walk from one another. That means it’s easy to put together a Chicago sightseeing itinerary that will keep you entertained without wearing you out.
Must-See Chicago Attractions
Ask a Chicagoan what it’s like to live here and love it, and he or she will probably point you to the following unforgettable Chicago attractions.
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Chicago Architectural River Cruise Tour
A Chicago sightseeing experience wouldn’t be complete without immersing yourself in the city’s architectural history aboard a Chicago River cruise. The 90-minute Chicago’s First Lady cruises, run by the Chicago Architecture Foundation, incorporate city history into tours focused on explaining architectural styles represented by more than 50 buildings flanking the Chicago River. Chicago Line Cruises‘ 90-minute tours, associated with the Chicago History Museum, discuss architecture in historical context, including the Great Chicago Fire of 1871 that gave rise to the legendary skyscrapers and soaring glass towers visitors marvel at today.
Grant Park
Chicagoans call 319-acre Grant Park their “front yard” because it’s their favorite place to promenade, picnic, party, and play. Grant Park encompasses several smaller green spaces, including Millennium Park, where must-see Chicago attractions include the giant bean-shaped “Cloud Gate” sculpture, the digitally animated Crown Fountain, the Art Institute of Chicago, and the Harris Theater for Music and Dance. At Maggie Daley Park, families clamber up a climbing wall and, in winter, skate the ice ribbon. On Grant Park’s south end are historic Buckingham Fountain and the Field Museum of Natural History, Shedd Aquarium, and Adler Planetarium. Sprawling green lawns along the lakefront stage Chicago’s blockbuster festivals including Taste of Chicago, Lollapalooza, and Chicago Blues Festival.
Art Institute of Chicago
The venerable Art Institute of Chicago showcases one of the world’s largest permanent collections of Impressionist paintings in addition an extensive assortment of Chinese bronzes, medieval arms, American art, and contemporary masterpieces. Take in vibrant Marc Chagall’s vibrant stained-glass “American Windows” installation, or wander through the charming Thorne Miniature Rooms displaying dollhouse-sized rooms decorated in every historical interior design style. Short on timme? Select one or more of the free themed mini-tours.
Michigan Avenue
A stroll down Michigan Avenue is simply required of all Chicago visitors. (A romantic horse-drawn carriage ride counts, too!) The famous boulevard known for its luxury hotels, historic landmarks, and entertainment venues traces the original shoreline of Lake Michigan. The blocks from Oak Street south to the Chicago River are called the “Magnificent Mile,” a swank shopping and dining district. Hidden gem Chicago attractions tucked into Michigan Avenue skyscrapers include the American Writers Museum, Chicago Sports Museum, Spertus Institute of Jewish Learning and Leadership, and Pritzker Military Museum and Library. Duck into the Chicago Cultural Center to see the world’s largest Louis Comfort Tiffany glass dome.
Museum Campus
It’s easy to spend a day or two in these three top-notch museums on the lakefront Museum Campus, one of the most popular places to visit in Chicago. Dolphins, beluga whales, penguins, and an 80-year old lungfish are just a few of the 32,000 animals living at Shedd Aquarium. Don’t miss the Caribbean Reef exhibit, where divers hand-feed sharks and exotic fish. Adler Planetarium wows visitors with ever-changing, high-tech celestial sky shows and space exploration exhibits, including the Gemini 12 spacecraft. The Field Museum of Natural History ranks high on visitors’ Chicago sightseeing lists to meet Sue, the largest complete Tyrannosaurus rex ever unearthed. Another crowd pleaser is the “Inside Egypt” exhibit, displaying real mummies.
Chicago Riverwalk
There’s no better way to experience the city’s architecture, dining, and nightlife than strolling the Chicago Riverwalk stretching from Lake Michigan west to Franklin Street. The continuous waterfront walkway passes iconic skyscrapers, tiered gardens, public art, and spouting fountains. Chicago Riverwalk activities include boat cruises, kayak rentals and tours, pier fishing, and Audubon-guided bird walks. Learn about the waterway’s history and its moving bridges at the McCormick Bridgehouse & Chicago River Museum.
The Ledge at Willis Tower
Chicago sightseeing reaches new heights at the Willis Tower’s Skydeck on the 103rd floor. Visitors can survey city and lake views as far as the eye can see—and that’s into three neighboring states on a clear day. For an extra adrenaline rush, step onto The Ledge to gaze down from one of four cantilevered glass boxes suspended 1,353 feet above the busy Loop streets.
Museum of Science & Industry
As one of the world’s largest science museums, the Museum of Science & Industry in Hyde Park is one of the most popular places to visit in Chicago—especially for families. Headliner exhibits include the only German World War II U-505 submarine ever captured and the “Science of Storms” simulation of tsunamis, tornadoes, and avalanches. Kids love the underground coal mine and “The Great Train Story,” an exhibit of 20 model trains traveling through miniature U.S. landscapes between Seattle and Chicago.
Wrigley Field
Even before the Cubs became the 2016 World Series champions, their home field ranked as a top Chicago attraction. Built in 1914, the nation’s second-oldest baseball park sports a classic grass field, hand-turned scoreboard, old-school bleacher seats, and ivy-strewn walls. Behind-the-scenes ballpark tours are offered seasonally, and concerts held in this historic sports venue knock it out of the park.
More from SmarterTravel:
- Chicago Travel Guide
- 9 Best Hotels in Chicago
- 10 Best Cheap Hotels in Chicago
- 9 Stylish Boutique Hotels in Chicago
- 10 Best Day Trips from Chicago
- Chicago with Kids: 9 Fun Family-Friendly Activities
- 10 Best Cheap Eats in Chicago
- 10 Best Places for Chicago Deep-Dish Pizza
- 10 Best Restaurants in Chicago
- What to Wear in Chicago
- What to Pack for Chicago
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—Original reporting by Kit Bernardi
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.
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