Things to Do in Chicago
The Windy City is arguably the capital of the Midwest, but this metropolis on the shores of epic Lake Michigan isn’t too full of itself. Though it boasts cultural, architectural, culinary, and entertainment highlights, the vibe is accessible and welcoming to residents and visitors alike. The Loop, Chicago’s downtown, is home to the city’s most famous buildings—including the Willis (Sears) Tower—and defined by the El (elevated train) routes that circle the city before jutting out into outlying neighborhoods. In Lincoln Park, twentysomethings pack into sports bars and chic boutiques; coffee shops and dive bars abound in Wicker Park; Logan Square is typified by tree-lined boulevards of stately historic houses; and multimillion-dollar abodes line the Gold Coast. Most travelers stick to the North Side, but you'll be rewarded for venturing south to check out Hyde Park and the University of Chicago neighborhood, a haven for academic types and home to the Museum of Science and Industry. A Chicagoan’s perfect day might include visits to the Art Institute of Chicago, Millennium Park, or Shedd Aquarium (all within 2 miles/3.2km of each other), deep-dish pizza at Lou Malnati’s, a Cubs game at Wrigley Field, dinner at one of the many celebrity chef-helmed restaurants, and an overnight stay at Palmer House Hilton. Although winters are notoriously harsh due to the “lake effect” snow, summers bring block parties and festivals galore, as well as the opportunity to lounge on Lake Michigan beaches.
- Language: English
- Currency: $
- Time Zone: UTC (-6:00)
- Country Code: +1
- Best Time to Visit: Summer, Fall
When to Visit: After being cooped up all winter, Chicago is ready to party when the sun comes out (sometime during May). Summer highlights include the annual Taste of Chicago, Chicago Blues Festival, Andersonville’s Midsommarfest, and the Chicago Air and Water Show. Alternatively, fall brings fewer crowds and brisker weather, perfect for exploring neighborhoods on foot and watching the trees turn colors along the quaint neighborhood streets.
The Chicago Transit Authority (CTA) is your best friend when traveling around Chicago. You’ll see many references to “the Loop,” the circle elevated train tracks that define the city’s downtown area. From there, train lines (both underground and elevated) shoot out to the airport and the nearby suburbs. The CTA also has a robust network of bus lines that make all corners of the city easily accessible. The Loop itself is very walkable, and if you’re there in the dead of winter and your toes are frozen, hailing a cab is a cinch.
Tipping: As in the rest of the US, tipping is common and how most service staff make the majority of their income. Between 10% and 20% is standard at an eatery, in a cab, or for personal services like a haircut or massage.
You Might Not Know...: The best place for a chargrilled Chicago hot dog after bar closing time (2 a.m.) is the Weiner’s Circle in Lincoln Park. The dog is served with a pickle, tomato wedges, chopped onions, sweet peppers, celery salt, and a side of major sass from the counterperson. If you know what’s good for you, never ever ask for ketchup—Chicago is a mustard town.
Navy Pier is one of Chicago’s most popular tourist destinations—and with good reason. The 3,300-foot (1,010-meter) pier jutting into the waters of Lake Michigan, originally constructed in 1916 as a freight dock and public space, encompasses almost 50 acres (20 hectares) of exhibits, rides, parks, and family attractions.
Once the world’s tallest building when it opened in 1973 as Sears Tower, Willis Tower is still way up in the clouds. The 1,454-foot (443-meter) skyscraper reigns as the third tallest building in all of North America with its spires just 325 feet (99 meters) shorter than Manhattan’s One World Trade Center. Though it functions as an office tower, the skyscraper’s 103rd-floor Skydeck Chicago draws 1.7 million annual visitors for a trip out onto The Ledge, an enclosed glass balcony extending four feet (1.2 meters) outside the 103rd floor, and for panoramic views that, on clear days, extend as far as Indiana, Michigan, Iowa, and Wisconsin.
Winding its way through the heart of the Windy City, the Chicago River flows past some of the city’s most notable architecture, including the Willis Tower (formerly the Sears Tower), Wrigley Building, and Navy Pier. The river also offers opportunities for exploration, such as river cruises, kayaking, and canoeing, along a revamped riverfront.
Located just a block away from Lake Michigan in the heart of downtown Chicago, Millennium Park showcases world-class art, music, architecture, and landscape design. Completed in 2004, the 24.5-acre (10-hectare) park is one of Chicago’s most popular destinations, drawing 25 million visitors per year.
Connecting Lake Michigan to downtown, the Chicago Riverwalk is an open-air pedestrian-friendly walkway that runs along the Chicago River. Composed of six main sections, the Riverwalk is a main hub for entertainment. Head to the Marina Plaza section for restaurants, outdoor seating, and boat access. Take a stroll through a series of piers and floating wetland gardens at the Riverbank, or head to the Water Plaza where the kids can splash in water fountains.
Known as “Chicago’s Front Yard,” Grant Park stretches over 300 acres (121 hectares), and is the city’s primary downtown park. Located in the Loop, Grant Park is sandwiched between Lake Michigan and soaring skyscrapers. Its cultural highlights include the Art Institute of Chicago, the Museum Campus, and Millennium Park.
The 1920s were an important time for Chicago architecture, and when the Wrigley Building opened in 1925, it set the pace for the city’s development. When owner William Wrigley Jr. (of the Wrigley gum company) scouted locations for the building that would become his company’s headquarters, he chose a unique triangle shape of land that eventually became the bustling Magnificent Mile.
The dueling main columns of Marina City overlook the Chicago River. Its scalloped “corn-on-the-cob” exterior, formed by undulating half-moon balconies, has made it instantly recognizable and a popular setting in movies such as Batman Begins, Ferris Bueller’s Day Off, and The Blues Brothers. While the historic buildings are largely residential—some 1,400 people call Marina City home today—visitors are welcome to the complex. You can head up to roof decks for 360 degree views of the city skyline, rent boats in the attached marina to explore the Chicago river, dine in restaurants like Smith and Wollensky’s Grill, catch a concert in the House of Blues, and even use the structures’ ice skating rink, swimming pool, and bowling alley.
Marina City’s 588-foot towers, designed by great Chicago architect Bertrand Goldberg, were the tallest residential structures and the tallest concrete buildings in the world when they were constructed in the early 1960s. Forty-stories of pie-shaped apartments, designed to emphasize city views, sit atop twenty stories of parking. Designed as a “city within a city,” with shopping, dining, office buildings, recreational spaces, and entertainment for its residents, the then-novel concept was part of a movement encouraging Chicagoans to return to downtown from the suburbs.
Fashion, architecture, and history in Chicago come together on this renowned stretch of Michigan Avenue nicknamed the Magnificent Mile. As you walk from the Chicago River to Oak Street, you’ll pass several Windy City landmarks, including the Water Tower, John Hancock Center, and Tribune Tower, as well as numerous luxury brand retailers.
Opened in 1897 as Chicago’s first public library, the Chicago Cultural Center is the city’s hub for arts and cultural events as well as one of the city’s most beloved architectural monuments. The center is among Chicago’s most popular tourist attractions and features more than 1,000 free concerts, films, art exhibits, and other cultural events each year.
More Things to Do in Chicago
Once home to the Chicago Tribune, this neo-Gothic landmark was built as a result of the International Design Competition in 1922. Before this 462-foot (141-meter) building was constructed, reporters from the paper brought back pieces of rock from important landmarks around the world like the Taj Mahal, the Hagia Sophia, the Great Wall of China, and more.
Once the world’s largest indoor aquariums, Chicago’s Shedd Aquarium is home to more than 1,500 species of fish, marine mammals, birds, snakes, and amphibians. The aquarium sits on the shores of Lake Michigan and is part of Chicago’s famous Museum Campus, which includes the Field Museum and Adler Planetarium.
In a city of skyscrapers, the Chicago Board of Trade Building stands out. Its history dates back to 1821, though the structure standing today was erected in 1930. Built for the Chicago Board of Trade, today it still serves as a center of Chicago’s financial district as the trading venue for the derivatives exchange. It stood at the tallest building in Chicago for many years. Today it remains a gateway to the city’s financial district.
The traditional art deco architecture draws tourists to the Chicago Board of Trade Building. A three-story statue of Ceres, the goddess of agriculture, stands atop the building on a copper pyramid, drawing visitors from all over the city to see the exquisite craftsmanship. The 6,500 pound Ceres represents the time when agriculture ruled Chicago. The 12-story building has a 19,000 square foot trading floor. Statues adorn the building, each of which tells a different story of the type of work that goes on inside.
Located in Chicago’s Grant Park, the Art Institute showcases 300,000 works of art ranging from ancient works to pieces created by today’s foremost artists. More than 1.5 million visitors from across the globe flock to the museum annually, making it one of Chicago’s most-visited destinations.
Chicago’s largest park and a leisure destination for locals and visitors alike, Lincoln Park abuts its namesake neighborhood. This massive green space serves as a welcome escape from the urban hustle and bustle, whether it be for a short picnic lunch break or a day spent lounging and exploring.
With more than 20 million artifacts, the Field Museum is an engaging museum filled with both interactive and imaginative displays. The big attraction is the Tyrannosaurus rex named "Sue," a 13 foot (4 meter) tall, 41 ft (13 m) long beast who menaces the grand space with ferocious aplomb. The most complete T-Rex ever discovered, it takes its name from Sue Hendrickson, the fossil-hunter who found the 90 percent complete skeleton in South Dakota in 1990.
Dinosaurs loom large in the Field Museum. At the Evolving Planet exhibit, you can also watch staff paleontologists clean up fossils, learn about the evolution of the massive reptiles, and even learn about Homo sapien's evolutionary ties to the extinct beasts. Away from the prehistoric giants, the “Inside Ancient Egypt” exhibit recreates an Egyptian burial chamber on three levels. The mastaba (tomb) contains 23 actual mummies. The bottom level, with its twisting caverns, is especially worthwhile. Those reeds growing in the stream are real.
Other displays worth your time include “Underground Adventure,” a vast exhibit exploring the habitats of animals and insects that live underground, and the “Pawnee Earth Lodge,” which allows visitors to explore a complete dwelling of the Great Plains tribe.
The historic Chicago Theatre, which dates back to 1921, is a popular downtown architectural landmark. With its famous dazzling marquee, French baroque architecture, and lobby modeled on a Versailles chapel, this picturesque structure today hosts concerts and comedy shows, as well as daily tours of its spectacular interior.
Formerly known as the John Hancock Observatory, 360 Chicago offers an interactive experience of the Windy City’s history and culture on the way up to its 94th-floor observation deck. From here, sweeping views of the Chicago skyline and Lake Michigan are enhanced by Tilt—moving glass lookouts that that literally tilt you out 1,000 feet (305 meters) above the Magnificent Mile.
Chicago’s central business district, the Loop, is home to many of the city’s most recognizable landmarks, from museums and skyscrapers to parks and outdoor sculptures. Renowned for highlights like Grant Park, City Hall, and the Willis Tower, the Loop attracts both locals and visitors with its culture and entertainment offerings.
Home to the Chicago Bears and host to numerous concerts, festivals, and other blockbuster events throughout the year, Soldier Field is one of Chicago’s major athletic and entertainment venues. Built in 1924 and named in honor of fallen soldiers, the stadium has hosted the Windy City’s National Football League team since 1971.
Part of Chicago’s Museum Campus in Grant Park, the Adler Planetarium dates to 1930 when Chicago businessman Max Adler opened it as the first planetarium in the western hemisphere. See its family-friendly planetarium shows, celestial artifacts, and the immersive Grainger Sky Theater, which opened in 2011.
Chicagoans take their baseball seriously, and one of best places to see a Major League Baseball game in the United States is at the ivy-covered home of the Chicago Cubs: Wrigley Field. Built in 1914 and known as the "Friendly Confines," Wrigley Field is the oldest baseball park in the National League and should be on the bucket list of any baseball fan.
An official Chicago landmark and an architectural masterpiece, the Rookery Building was one of the city's tallest and most expensive buildings when it was completed in 1888. A 1905 renovation by Frank Lloyd Wright transformed the lobby into a light-filled courtyard admired by office workers and visitors to this day.
Hugging the shoreline of Lake Michigan for nearly 19 miles, the Chicago Lakefront Trail — also known as the Lake Michigan Trail — is a popular path for walkers, runners, and cyclists that connects urban neighborhoods with green spaces, downtown attractions, and some of Chicago’s best lakeside and skyline views.
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