Top 12 best Things to do in Chicago, Illinois

Last Updated on February 23, 2024 by Emily Johnson

Chicago is one of the most vibrant and exciting cities in the United States. Known for its world-class architecture, stunning lakefront views, amazing food scene, and rich history, the Windy City has something for everyone. From iconic landmarks and legendary sports teams to an incredible arts and culture scene, Chicago dazzles locals and visitors alike.

ActivityDescription
Millennium Park & “The Bean”Iconic outdoor space and sculpture.
Wrigley FieldHistoric baseball stadium.
Art Institute of ChicagoPremier art museum.
Untouchables TourMobster history tour.
River Architecture TourArchitectural boat tour.
The Magnificent MileShopping and dining district.
Willis Tower SkydeckHigh observation deck.
Millennium and Grant ParkMajor urban parks.
Navy PierEntertainment complex on the waterfront.
Lincoln Park ZooFree-admission zoo.
North Avenue BeachPopular lakefront beach.
The Second CityFamous comedy club.
Chicago-Style PizzaMust-try local cuisine.

Boasting 77 distinct neighborhoods, each with its own unique character and charm, exploring Chicago feels like discovering 77 different towns, each with something special to offer. Skyscrapers scrape the clouds alongside quaint tree-lined streets, and locals take as much pride in their neighborhood taverns and hot dog stands as they do in the city’s famous museums and theaters.

While choosing what to do in Chicago among hundreds of options can feel overwhelming, some experiences are simply not to be missed. Here are the top 12 things to do in Chicago, Illinois to make the most out of your visit to this Midwestern gem on the shores of Lake Michigan.

1: Visit Millennium Park and “The Bean”

Name and Location: Visit Millennium Park and “The Bean” sculpture in downtown Chicago.

History and Significance: Opened in 2004, Millennium Park has become a landmark cultural destination, known for public artworks like Cloud Gate (The Bean).

What to Expect: See Cloud Gate’s mirrored design, the Crown Fountain’s faces, outdoor concerts at Pritzker Pavilion, art exhibitions, and gardens.

Visitor Information: Millennium Park is open daily from 6am to 11pm, admission is free.

Sprawling across 24.5 acres in the Loop, Chicago’s city center, Millennium Park has transformed from an urban eyesore into a world-class attraction since opening in 2004. Free and open 365 days a year, Millennium Park is now Chicago’s crown jewel and the city’s most popular tourist destination.

The park’s iconic centerpiece is Cloud Gate, affectionately known as “The Bean” for its gleaming, bean-shaped structure. This massive, mirror-like sculpture reflects both Chicago’s skyline and the clouds above while visitors walk underneath its 12-foot arch. Seeing their warped reflections in the fun house mirror-like surface makes for fun photos and memories.

In addition to serving as the backdrop for selfies and photo ops, visitors also appreciate Cloud Gate for its awe-inspiring, artistic beauty and impressive engineering. British artist Anish Kapoor specially designed the 110-ton stainless steel structure to become part of Chicago’s landscape, constantly changing with the angle of sun and the time of day.

2: Cheer on the Cubs at Wrigley Field

Name and Location: Cheer on the Cubs at Wrigley Field in the Lakeview neighborhood.

History and Significance: Open since 1914, historic Wrigley Field is one of baseball’s iconic ballparks and home to the Chicago Cubs.

What to Expect: Catch an MLB game April-September and enjoy the lively atmosphere, traditions, snacks and views inside America’s second oldest ballpark.

Visitor Information: Game tickets vary in pricing. Tours are available on non-game days for $25.

No trip to Chicago is complete without attending a baseball game at the city’s beloved Wrigley Field. Built in 1914, this historic stadium is home to the Chicago Cubs and the city’s most iconic sports venue. With its ivy-covered brick walls, old-fashioned manual scoreboard, and lively atmosphere, going to a game at Wrigley Field is like stepping back in time.

Beyond baseball, Wrigleyville around the stadium offers an entire day and night of entertainment. Grab some drinks on the patio at one of the lively sports bars, browse the nearby shops stocked with Cubs gear, and soak up the infectious energy buzzing through the neighborhood. Locals and visitors alike pack Wrigleyville on game days for a tailgating, beer swilling, hot dog eating celebration of America’s favorite pastime.

If you can’t get tickets to a game, at least take a photo outside the iconic red marquee and see if you can catch a glimpse inside during a stadium tour.

3: Marvel at the Art Institute of Chicago

Name and Location: Marvel at the Art Institute of Chicago in Grant Park.

History and Significance: Founded in 1879, this world-class museum houses an exceptional collection of art spanning many cultures and time periods.

What to Expect: See iconic works like American Gothic, Monet gardens, Warhol’s soup cans, Chagall stained glass, Picasso sculptures, artifacts, photography and more.

Visitor Information: Open daily (closed Thanksgiving/Christmas) from 10:30am-5pm. Admission is $25.

Known as one of the oldest and most influential art museums in the United States, the Art Institute of Chicago showcases more than 300,000 masterpieces from around the world, spanning ancient works to contemporary pieces. Housing everything from Monet paintings to Andy Warhol prints under one roof, you can admire iconic works like Grant Wood’s American Gothic and Edward Hopper’s Nighthawks between its vast galleries and corridors.

Beyond its permanent collection, the Art Institute also hosts world-class special exhibitions and events. Recent shows highlighted the works of Frida Kahlo, Claude Monet, Yayoi Kusama, and Salvador Dalí. Grab lunch at the museum’s upscale café Terzo Piano, relax in its sculpture garden overlooking Millennium Park, or join a guided tour to learn the backstories behind some of the greatest art in history.

4: Learn about Chicago’s mobster past on the Untouchables tour

Name and Location: Learn about Chicago’s mobster past on the Untouchables tour, departing from Michigan Ave downtown.

History and Significance: During Prohibition, gangster Al Capone maintained criminal operations headquartered in Chicago before federal authorities intervened.

What to Expect: Led by guides dressed as 1920s gangsters and federal agents, the 2-hour bus tour visits famous crime scene locations while sharing stories.

Visitor Information: Untouchables tours run multiple times daily. Rates start at $37 for adults. Advance purchase recommended.

In the early 20th century, Chicago earned the nickname “Capitol of Crime” for its notorious mobsters and rampant criminal underworld. Al Capone and his gang terrorized the city throughout the Prohibition era, controlling everything from illegal breweries to speakeasies, gambling dens, and brothels.

Today, visitors can relive Chicago’s roaring ’20s mobster past through organized tours of famous crime scenes and historic hot spots. Step back in time with stops at sites like Holy Name Cathedral, the scene of the St. Valentine’s Day Massacre, and the former Lexington Hotel where Al Capone orchestrated his dirty work. Tour guides relay spine-tingling tales about Capone, his rivals like Bugs Moran, and the bloody battles between Chicago’s warring bootlegging gangs.

Between mobster history and haunting stories from the Prohibition era, Chicago’s gangland tours offer a thrilling glimpse into the city’s notorious past.

5: Take a River Architecture Tour for Magnificent Views

Name and Location: Take a River Architecture Tour departing from the downtown riverwalk.

History and Significance: The 90-minute cruise navigates all three branches of the Chicago River, highlighting prominent architecture and skyscrapers along the waterfront.

What to Expect: Listen to live commentary on buildings while seeing famous towers like Willis Tower, Marina City, Tribune Tower and the Merchandise Mart from river level.

Visitor Information: Public tours run multiple times daily April–November. Tickets are $44 for adults.

One of the best ways to fully appreciate the towering Chicago skyline is gliding underneath it on a river architecture tour. The Chicago River cuts right through the middle of downtown, lined with architectural wonders. More than 50 buildings along the river stand over 20 stories tall, creating a jaw-dropping cityscape.

From the water, you’ll see famous Chicago skyscrapers like the Willis Tower, Tribune Tower, and Marina City, plus newer additions like the spiraled CNA Center. Hear the backstories behind these iconic structures and more from your informative tour guide. Gliding past the magnificent skyline while learning about Chicago’s architectural impact and history makes for an unforgettable experience.

At night, the glittering city lights reflecting on the water make for an even more magical river tour.

5: Explore The Magnificent Mile

Name and Location: Explore The Magnificent Mile on Michigan Avenue downtown.

History and Significance: Dating from the 1890s, this upscale district stretches along 13 blocks, packed with luxury retailers, landmark buildings, hotels and restaurants.

What to Expect: Shop brands like Gucci, Cartier and Burberry, grab dinner, gaze up at top Chicago skyscrapers, people watch and take in the energetic vibe.

Visitor Information: The Magnificent Mile is openly accessible daily. Attractions may have varying hours.

Shopaholics and window shoppers flock to The Magnificent Mile, Chicago’s premier commercial district. This bustling 13-block stretch along Michigan Avenue features over 460 stores, 275 restaurants, 60 hotels, theaters, and amazing landmarks.

Even if you’re not looking to shop, just taking in the magnificent sights along this grand avenue feels like strolling through Times Square or the Champs-Élysées. From massive flagship department stores like Macy’s and Bloomingdale’s to luxury designers like Burberry and Louis Vuitton, this mile-long strip provides an incredible display of Chicago’s retail power.

In addition to incredible shopping and dining, visitors will find architectural marvels, iconic landmarks, and public art installations scattered throughout The Magnificent Mile. Stop for photos at the Wrigley Building, Tribune Tower, and Chicago Water Tower, visual symbols of the city’s resilience after the Great Chicago Fire of 1871. Public art like the iconic Chicago Picasso sculpture also dazzle along this jam-packed avenue.

6: Take in Stunning Views from the Willis Tower Skydeck

Name and Location: Take in Stunning Views from the Willis Tower Skydeck downtown.

History and Significance: Once the world’s tallest building at 1,450 feet tall, Willis Tower’s 103rd floor Skydeck offers unparalleled city sightlines.

What to Expect: Take in panoramic Chicago views spanning up to 50 miles from transparent ledge boxes extending out from the Skydeck.

Visitor Information: Open daily 9am-10pm. Tickets from $27. Advance purchase advised.

As the tallest building in the Western Hemisphere upon completion in 1974, the Willis Tower (formerly the Sears Tower) remains an iconic fixture in the Chicago skyline. Beyond admiring it from the ground, taking in the breathtaking views from the Skydeck on the 103rd floor is an absolute must.

Step out onto The Ledge, enclosed glass bays extending 4.3 feet outside the skyscraper’s walls and 1,353 feet above the ground. Peer straight down through the glass floor for a thrilling sense of floating in midair over Chicago. Look out across the sweeping cityscape in all directions for views stretching across four states on a clear day. Also explore interactive exhibits displaying fun skyscraper facts and Chicago history.

Skydeck tickets also grant access to Skydeck Chicago, an engaging 60th floor exhibition with panoramic views of the city’s development over nearly two centuries.

7: Spend an Afternoon in Millennium and Grant Park

Name and Location: Spend an Afternoon in Millennium and Grant Park downtown along Michigan Lake.

History and Significance: These adjoining parks anchor downtown with popular attractions, gardens, event venues and recreational spaces spanning 319 acres.

What to Expect: Relax outdoors at one of the world’s largest rooftop gardens, visit epic museums or public artworks, rent bikes, dine al fresco by the water.

Visitor Information: Millenium & Grant Park are open daily from 6am to 11pm. Free admission.

In addition to the lively attractions of Millennium Park, the greenery and trails across the rest of Grant Park also beg exploring. Spend an afternoon wandering through these sprawling downtown parks filled with public art, gardens, and cool landmarks.

Have a picnic on the grass, play in the magical Crown Fountain with kids, and pose by the imposing Chicago Landmark statues of Abraham Lincoln and George Washington. Stroll down the Nichols Bridgeway connecting Millennium Park to the Art Institute for architecturally stunning city views. On a nice day, grab food from an on-site food truck and relax on the Jay Pritzker Pavilion’s great lawn, which hosts free concerts throughout the summer.

With so much to do across these adjoining parks, you can easily lose an afternoon enjoying the urban oasis and fresh air in the middle of downtown.

8: Explore Navy Pier

Name and Location: Explore Navy Pier on Lake Michigan.

History and Significance: Opened in 1916 as a municipal pier and entertainment venue, the 3,300-foot Navy Pier remains a top attraction showcasing rides, shops, dining and more.

What to Expect: Ride the iconic Centennial Wheel, visit museums and exhibitions, dine at restaurants, take a boat cruise and enjoy street performances.

Visitor Information: Navy Pier is open from 10am-8pm in winter, with extended summer hours (til 10pm). Entry is free.

Jutting straight into Lake Michigan, Navy Pier stretches over three city blocks and stands as Chicago’s most-visited attraction. The pier provides panoramic views of the skyline, the vast lakefront, and the beaches lining the water. Between rides, restaurants, shows, and more, Navy Pier offers endless options for family fun.

Kids love the Ferris wheel and classic carousel, while adults appreciate the breweries and unique dining options. Catch an IMAX movie at the 3D theater, laugh at improv comedy shows, marvel at street performers, and explore the Pier’s many shops. The Chicago Children’s Museum and Chicago Shakespeare Theater also reside on Navy Pier, rounding out the cultural offerings.

Fireworks displays in summer and an indoor ice rink in winter make Navy Pier a year-round entertainment hub.

9: Experience Nature at the Lincoln Park Zoo

Name and Location: Experience Nature at the Lincoln Park Zoo in Lincoln Park neighborhood.

History and Significance: Founded in 1868, LPZ is an acclaimed free zoo focused on science and conservation, featuring naturalistic habitats across 35 acres.

What to Expect: Observe lions, snow monkeys, gorillas, polar bears and other global species roaming lush open-air exhibits modeled after natural settings.

Visitor Information: Lincoln Park Zoo is free and open daily all year from 10am-5pm.

Home to over 200 different animal species, the Lincoln Park Zoo lets you enjoy a safari adventure right in the heart of Chicago. As one of the last free major zoos left in America and seeing over 5 million visitors annually, this 35-acre zoo has something for everyone.

Get up close and gawk at the zoo’s amazing reptile collection, including rare Komodo dragons, or roam through the enormous Kovler Lion House. Hand-feed a giraffe, watch the gorillas and chimpanzees play, and see exotic wildlife from polar bears and snow monkeys to Emperor penguins.

Active and endangered species conservation programs give the Lincoln Park Zoo an educational mission as well. Situated across from Lake Michigan in a huge public park, this free zoo makes for an outstanding (and budget-friendly) family outing.

10: Relax at North Avenue Beach

Name and Location: Relax at North Avenue Beach along Lake Michigan downtown.

History and Significance: Set against Chicago’s iconic skyline, this 1,000-foot stretch of sand draws sunbathers and volleyball players during summers since 1893.

What to Expect: Swim, sunbathe, play beach volleyball, sip drinks at Castaways Bar & Grill and take in breathtaking urban views at the beach.

Visitor Information: North Avenue Beach is open for the season Memorial Day to Labor Day 9am to 7pm.

During summer, locals flock to North Avenue Beach to enjoy the fun atmosphere and picturesque lakefront location. Conveniently located along Chicago’s North Side, this 1,000 foot stretch of sand provides the ideal urban escape.

Go for a dip in the refreshing lake waters, play a competitive game of beach volleyball, or simply relax on the shore. Beachside concessions and equipment rentals make for a perfect beach day. Chicago’s offshore breeze keeps the beach from getting too hot, though the sand still buzzes with lively energy.

Watch elaborate sandcastle sculptures rise along the shoreline as sculptors celebrate Chicago’s vibrant sandy beach culture. In addition to swimming and sunbathing, North Avenue Beach hosts yoga classes, running clubs, and summer sport leagues for year-round fun and recreation.

11: Catch a Show at The Second City

Name and Location: Catch a Show at The Second City comedy theater on North Wells St in Old Town.

History and Significance: Launched in 1959, this Chicago improv venue helped launch comedies like John Belushi, Tina Fey, Steve Carell through its signature satirical revues and sketch shows.

What to Expect: See Chicago’s best up-and-coming comedians in outrageous improvised sets and well-known Mainstage productions.

Visitor Information: Showtimes vary by day. Tickets run $15 and up. The theater also offers classes.

As the first ever improvisational theater troupe in the United States, The Second City has launched comedic greats like John Belushi, Tina Fey, Stephen Colbert, and more. Attending an original sketch and improv show at this legendary theater is a quintessential Chicago experience.

Shows change regularly, featuring new young talent and sketches that parody current events and modern life. Enjoy some gut-busting laughs over drinks and bar food in the on-site UP Comedy Club after the performance. Beyond its theater, The Second City also offers multi-week improv classes for any aspiring comedians hoping to master this famously Chicago brand of comedy.

12: Chow Down on Chicago-Style Pizza

Name and Location: Chow Down on Chicago-Style Pizza found throughout the city.

History and Significance: Chicago is famed as the home of deep-dish “pie” pizza with its thick crusts, meaty fillings and bountiful melted cheese since the mid-20th century.

What to Expect: From local institutions like Lou Malnati’s to national chains, savor delicious pizza with creative toppings piled high in an overflowing deep pan or cast-iron skillet.

Visitor Information: Popular pizza restaurants often have long waits on weekends. Pricing based per pie or slice.

Sure, you can find deep dish pizza across the country now, but Chicago still reigns as the iconic homeland to this decidedly decadent style of pizza. The buttery crust heaped with molten cheese and thick tomato sauce over tons of toppings makes for an over-the-top indulgent meal.

Local pizza joints like Pizzeria Uno, Lou Malnati’s, and Gino’s East perfected and popularized the signature deep dish recipe across Chicago. Though locals argue over who does it best, visitors can’t go wrong sampling this famous regional specialty at any of the top spots slinging slices. Just come hungry, as Chicago-style pizza is definitely a knife and fork meal!

Conclusion

Between world-famous museums, breathtaking architecture, delectable cuisine, and endless things to do, Chicago dazzles visitors with its diversity and excitement. Iconic attractions like Willis Tower and Wrigley Field combine with vibrant neighborhoods, stunning parks, and lively entertainment for an incredible travel destination.

Use this list of top things to do in Chicago to hit the highlights and make the most of your Windy City vacation. Whether traveling solo, with a partner, or with a family, Chicago offers memorable adventures and quintessential Midwest culture perfect for every visitor.

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