Looking to pack your Chicago itinerary with awesome activities? Our guide to all the best things to do in Chicago will make sure you don’t miss a thing!
If you were to stand on the surface of Lake Michigan, the Chicago skyline would appear before you like a grand gate harboring an endless collection of attractions and memories.
Known as the Windy City, Chicago has eye-catching architecture, a lively waterfront and diverse culture.
Historic buildings, including one that used to be the tallest on earth, are features of the bustling downtown. But so too are the museums placed along the lush green waterfront where stunning views captivate locals and visitors alike.
Beyond the sites, Chicago has a storied past, a rich sporting scene and several dishes that are as mouthwatering as they are iconic.
From the winter holiday season to the height of summer, there is no shortage of memorable Chicago activities.
Check out this 3-day Chicago Itinerary to help you plan your visit!
The Best Things to Do in Chicago, Illinois
You won’t have to spend a lot of time wondering what to do in Chicago.
Illinois’ biggest city has a wonderful diversity of activities that will help you stay busy and happy regardless of the weather.
Consider getting the Chicago CityPASS for your visit. It allows you to choose 5 of the top attractions and get a discounted price.
If you plan on visiting lots of museums or other hotspots like the planetarium, the 360 Observation Deck or the Skydeck, it’s worth getting the CityPass to save some money!
1) Millennium Park
At the top of the list of best things to do in Chicago is Millennium Park. Found within the larger Grant Park, the space is flanked by the brilliant Chicago skyline on one side and the sprawling Lake Michigan on the other.
At the heart of Millennium Park is Cloud Gate, aka the Bean. It’s an attraction that’s taken a transcendent status, enough to earn its own spot on our list.
But there’s more to the park than this iconic sight. Travelers can experience a vibrant waterfront with street performers adding tunes to the air and ample room for a picnic.
Another site you won’t want to miss is Crown Fountain, a spectacular piece of public art. Afterward, visit the beautiful Lurie Garen, or the Jay Pritzker Pavilion for outdoor concerts.
2) The Magnificent Mile
Coursing through the heart of downtown Chicago, the Magnificent Mile is a famed shopping destination.
However, alongside a healthy dose of retail therapy, you’ll find some of the best restaurants in town and historic landmarks flanked by soaring skyscrapers along eight thrilling blocks.
Travelers shouldn’t be worried about “completing” the Magnificent Mile. After all, it could take multiple trips to visit all 460 stores and dine at more than 250 restaurants.
But if you’re someone who likes to wander, window shop and try the local cuisine, then you’ll quickly find yourself exactly where you want to be.
If shopping doesn’t take your interest, then you’ll be captivated by a number of historic downtown buildings in the River North district. These include the neo-Gothic Tribune Tower, the Wrigley Building and the John Hancock Center.
At the end of the mile, you’ll arrive at the Chicago River, where you can then begin the Riverwalk.
Home to amusement parks, gardens, great eats and family fun, Navy Pier is one of the most beloved Chicago attractions.
The pier runs for six blocks out into Lake Michigan, providing travelers with gorgeous views of the lake and back to the endless city skyline.
On those calm summer days, the atmosphere at Navy Pier reaches its zenith. Crowds explore the 50 acres of space that boasts a long list of family-focused attractions from the soaring Ferris Wheel to the Funhouse Maze.
It’s here that you can also visit the Children’s Museum and Crystal Gardens before sticking around for the weekly fireworks.
Among the Chicago tourist attractions, which also include the Shakespeare Theater, are boisterous waterfront eateries and bars none better than the Miller Lite Beer Garden. You can also depart from various sightseeing cruises from Navy Pier.
4) The Art Institute of Chicago
One of the highlights of Grant Park, the Art Institute of Chicago, is not just an attraction for art aficionados.
The institute, which was founded in the 1870s, has become one of the top art galleries in the United States.
With over 300,000 pieces to see, many world regions are represented and the age of the works makes it as much a historical attraction as a creative one.
You’ll recognize many famous names as you wander through the many halls. You’ll stumble upon works by Picasso, Van Gogh, and Renoir. In fact, aside from Paris, no place has more Post-Impressionist work than the Art Institute of Chicago.
Beyond those famous names, you’ll find contemporary art by Warhol, Pollock and Matisse, along with designs from the iconic hand of Frank Lloyd Wright.
- Location: 111 S Michigan Ave, Chicago, IL 60603
- Opening hours: 11 AM – 5 PM (Thur-Mon)
- Price: $25 Adult, $19 child
5) Cloud Gate
As the most recognizable landmark in Chicago, no time in town would be complete without a selfie in front of Cloud Gate.
The Bean was created in 2006 and its beguiling design meant it quickly transcended beyond your typical tourist sight. It features a shiny, arch design that boasts almost 170 stainless steel plates that reflect all and sundry.
Beyond its intriguing shape, it’s the reflection that makes Cloud Gate such a popular thing to do. Owing to its mirror-like qualities, the photography is exceptional.
From afar you can take a pic of the Bean, which will include a reflection of the surrounding plaza and the Chicago sky.
While those who stand close will see a warped version of themselves splashed across the metal, perfect for your best selfie yet.
Heading west after Chicago? Check out this list of the best things to do in Denver, Colorado.
6) Grant Park
Featuring Millennium Park and the Art Institute, Grant Park is like an album containing the city’s greatest hits. But beyond the public art, fountains and galleries are over 310 acres of lush space, otherwise known as Chicago’s Front Yard.
Millennium Park forms the northern tip of Grant Park, but as you wander further south you’ll pass Butler Field, which looks up the Petrillo Music Shell and is a lively space for community events.
Continue on to discover the Buckingham Fountain, a three-story rococo fountain. It’s one of the largest in the world and dazzles under the stars at night.
You’ll soon reach the Museum Campus and the Field Museum, home to the largest T-Rex skeleton on earth.
Lastly, you’ll stop at Soldier Field. It’s a hodge-podge of attractions, but for locals, the open space is the perfect meeting point and place for a sunny picnic.
7) John Hancock Center
For over 50 years, the John Hancock Center has been at the forefront of the Chicago skyline. Found at the northern end of the Magnificent Mile, the skyscraper reaches the dizzying height 1,129 feet.
From street level, the building catches the eye thanks to its unique exterior with a slew of diagonal lines running up the facade.
But for travelers, it’s the view from the top of the tower that is the genuine star of the show. 360 Chicago is on the building’s 94th floor and offers thrilling views that reach well beyond the city limits.
The elevators sweep you up, taking you to the floor in under 40 seconds. Here, you’ll find food, drinks and exceptional vistas, none more heart-racing than the Tilt, which allows you to lean over the edge and see below.
- Location: 875 N Michigan Ave, Chicago, IL 60611
- Opening hours: 9 AM – 9 PM (Sun-Thur) 9 AM – 11 PM (Fri-Sat)
- Price: $30
NOMADasaurus Tip: Book your 360 Observation Deck entry ticket in advance on Get Your Guide. It’s the same price and you get to skip the line!
8) Lincoln Park Zoo
Since opening in 1868, the Lincoln Park Zoo has become such a part of local life that it’s often known simply as the Chicago Zoo.
Visiting the zoo is one of the best things to do in Chicago with kids. The range of animals here will keep the entire family entertained for hours on end. But the best news? It’s free.
After wandering inside, you’ll spot lions roaming the prairie, polar bears on ice and penguins frolicking about. There are also sections for apes, a petting zoo and several historic buildings that were built in the zoo’s founding years.
Outside the zoo is the wider Lincoln Park home to the Chicago History Museum, a conservatory and miles of biking trails.
- Location: 2001 N Clark St, Chicago, IL 60614
- Opening hours: 10 AM – 5 PM (Mon-Sun)
- Price: Free
9) Chicago History Museum
The Lincoln Park Zoo may be one of the oldest in the country, but that won’t be your only brush with history here. If you love stories from the past, then you can learn all about local history at the Chicago History Museum.
The museum showcases the events that shaped the Windy City from the first railroads in the early 19th century to the Great Chicago Fire in 1871.
Guests will also learn about Abraham Lincoln’s influence on Chicago, the Civil War, and suffrage.
The Chicago History Museum isn’t just board after board of reading. It’s interactive and often puts you in the chosen event. Hear the roar of the tragic fire, ride a high-wheel bike or even jump inside Chicago-style hot dogs.
- Location: 1601 N Clark St, Chicago, IL 60614
- Opening hours: 9.30 AM to 4.30 PM (Tue-Sat) 12 PM to 5 PM (Sun)
- Price: $19 Adult, $17 Child
10) The Chicago Riverwalk
Chicago is a great city to explore on foot. From the Magnificent Mile to the Lakefront Trail. But perhaps the best stroll in town is the Chicago Riverwalk.
The path winds along the Chicago River for 1.25 miles as the water makes its way to Lake Michigan.
There are several landmarks along the way, including the Wrigley Building and more additions to the bursting list of public art, such as Ellen Lanyon’s Gateway.
With the glistening water to one side, enjoy relative peace among the skyscrapers as you admire beautiful urban planning, tree-lined paths and vibrant restaurant patios.
If you’d rather get out on the water, why not join this romantic sunset cruise along the river?
11) Wrigley Field
Wrigley Field is second on the list of the oldest stadiums in Major League Baseball. It’s a historical landmark, one of the best places in the country to watch a ballgame and is surrounded by an electric village of pubs and restaurants.
If you’re keen to catch some live sport while wondering what things to see in Chicago, then there’s no better place to go.
The beloved ballpark features ivy that grows on the outfield walls, with the beauty of the field being as interesting as the action on it.
Travelers will be able to watch the Chicago Cubs go to work and if you’re lucky, maybe your own team as well.
If there aren’t any games while you’re in town, you can tour the iconic stadium, which includes visiting the field, dugout and press box.
Heading further east? Check out our list of the best things to do in Boston, Massachusetts.
12) Chicago Cultural Center
Housed within an arresting neoclassical building, the Chicago Cultural Center is as fascinating as it is budget-friendly.
Upon opening in 1991, it replaced the home of the Chicago Public Library and became the first free cultural center in the country.
Today, locals and travelers alike can experience over 1,000 annual events that cover an incredible range of topics. Without paying a dime, culture lovers can take part in film screenings, lectures, theater and exhibitions.
However, as you explore your chosen event, be sure to admire the stunning interior. The 19th-century building features gilded hardwood, brass, mother-of-pearl and eye-catching marble. While there are also two soaring domes.
- Location: 78 E Washington St, Chicago, IL 60602
- Opening hours: 10 AM – 5 PM (Mon-Sun)
- Price: Free
13) Museum of Science and Industry
Set back from Lake Michigan at the north end of Jackson Park, the Museum of Science and Industry is one of the most interesting things to do in Chicago.
The museum first opened in 1933 and for many travelers, it’s the best in town.
There’s no end to the hands-on nature of the space, with a highlight being the Science Storms exhibition that will have you searching for answers to big questions.
Some of the other memorable parts of the museum include a German submarine that was captured in WWII, the first commercial Boeing 727, and a diesel locomotive from the 1930s. But before leaving, venture deep into a replica coal mine on the mine train.
- Location: 5700 S DuSable Lake Shore Dr, Chicago, IL 60637
- Opening hours: 9.30 AM – 4 PM (Mon-Sun)
- Price: Free with costs for some exhibits
14) The Chicago Theatre
Whether you’re a fan of theater or not, the facade of the Chicago Theatre is not one to miss.
In 1921, the venue opened for the first time. Not much has changed over the last 100 years, with its entrance still capturing the hearts of locals and travelers.
From across East Lake Street, you can gaze upon the sparkling brilliance of the theater, its opulent facade and the horizontal neon sign, “Chicago.” The highlight is the arch that was inspired by Paris’ Arc de Triomphe.
After wandering through the classic entrance, you’ll get to enjoy the historic theater that now produces a range of live plays, along with stand-up comedy and concerts.
15) The Willis Tower
Once upon a time, the Willis Tower was the tallest on earth. New structures have put an end to that lofty reign, yet it still towers above the rest of the city center.
Once known as Sears Tower, the building reaches the heady heights of over 1,700 feet. Just like the Hancock Center, you’ll be able to enjoy stunning views from its observation decks, including Skydeck Chicago.
Regular viewing platforms will allow you to enjoy vast views of the city, the lake and the distant horizon. But the Skydeck, made entirely out of glass, is in a league of its own.
To take it up a notch, step into the Skydeck Ledge and walk out of Willis Tower with nothing but glass between you and the world below.
- Location: 233 S Wacker Dr, Chicago, IL 60606
- Opening hours: 9 AM – 10 PM (Sun-Fri) 8.30 AM to 10 PM (Sat)
- Price: $30-$44
16) Chicago Children’s Museum
Chicago offers traveling families a wonderful range of kid-friendly attractions. Another example of this is the insightful Chicago Children’s Museum.
Found on Navy Pier, the museum has over a dozen interactive attractions across its three stories. All balance education and fun.
Some of the dozen exhibits include Play It Safe. This is a sprawling indoor playground that also gives kids the opportunity to learn about fire safety.
Another attraction is the Tinkering Lab, where everyone can put their mind to work and create a masterpiece. While architecture and engineering is the focus at the Skyline exhibit.
To complement the permanent displays, the Children’s Museum has a rich calendar of unique events.
- Location: 700 E Grand Ave, Chicago, IL 60611
- Opening hours: 9 AM – 1 PM (Thur) 10 AM to 5 PM (Fri-Sun)
- Price: $19
Heading south into Texas after Chicago? Check out our Perfect 3 Days in Austin Itinerary
17) Adler Planetarium
In Museum Campus, the Adler Planetarium was the first of its kind to be built in the Western Hemisphere. It opened in 1930 and for decades it has thrilled visitors who can explore the night sky and venture far into outer space.
The building itself will capture your attention thanks to its soaring dome. But the outside world is quickly left behind as you walk inside. Sit down at the theater and fly through the solar systems or get to know the stars above Chicago.
Afterward, learn about the different planets, the meteors that have touched down on earth, and the world of astrology. You can even discover old sundials that were used in the early days of space exploration.
- Location: 1300 S DuSable Lake Shore Dr, Chicago, IL 60605
- Opening hours: 9 AM – 4 PM (Fri-Mon) 4 PM to 10 PM (Wed)
- Price: $35 Adult $24 child
18) Live Sport
Just like New York City, Chicago has five professional sports teams. This makes it one of the best places to go if you love a bit of sport on your travels.
Aside from Wrigley Field, home to the Cubs, Chicago’s United Center is where you’ll find the Bulls (NBA) and the Blackhawks (NHL).
The Chicago Bears (NFL) play out of Soldier Field and the city’s baseball team, the White Sox can be found slinging for the fences at Guaranteed Rate Field.
This means whatever time of year you arrive there’s going to be live sport for you to enjoy. The United Center and Soldier Field are both within easy reach of downtown Chicago.
19) The Shedd Aquarium
Looking over Lake Michigan, the Shedd Aquarium is your chance to explore life beneath the water all around the world.
The aquarium is home to over 35,000 animals, including everyone’s favorite terrifying beast, sharks, plus stingrays and colorful tropical fish.
But the aquarium is just a chance to learn about species that roam beneath the surface. There is a strong focus on different ecosystems, such as reefs and maritime habitats that each species rely upon.
Whether on a guided tour or through your own discovery, you can learn about life in the Caribbean, the Amazon and the Arctic that will help broaden your perspective of the world.
- Location: 111 S Michigan Ave, Chicago, IL 60603
- Opening hours: 9 AM – 5 PM (Mon-Fri) 9 AM – 6 PM (Sat-Sun)
- Price: $39.95 Adult $29.95 child
If you’re traveling to Colorado next be sure to consider our incredible 3 days in Denver Itinerary!
20) The Lakefront Trail
Spanning almost 20 miles along the shore of Lake Michigan, the Lakefront Trail is the best way to explore Chicago’s beautiful waterfront.
The wide and paved path leaves room for cyclists, joggers and walkers and takes you through many of the city’s top sites. This includes Lincoln Park, Grant Park, Navy Pier and the Museum Campus.
Owing to its length, the best way to experience the trail is on two wheels. It will take around two hours to complete the trail, although there’ll be many places you’ll want to stop at along the way.
But if you just want a sampler of the Lakefront, join this bike tour that takes you to the lake, and Wrigley Field plus the chance to eat local pizza and learn how to make a brownie. In the city that invented it, no less.
21) Deep Dish Pizza
Speaking of classic Chicago eats, you can head back to O’Hare International Airport without trying the city’s famous deep-dish pizza.
There is no shortage of places to try this delicacy, yet there are a handful that stand above the rest.
The best places to go include Uncle Jerrys, Burt’s Place and Bartolis. Here you can experience the delicious tall and flaky crust that harbors layer upon layer of mozzarella and chunky tomato sauce. Add on some fennel sausage for an extra burst of flavor.
Where to Stay in Chicago, Illinois
With the best Chicago activities covered, let’s turn our eye toward where to stay in the Windy City.
Best Hostel in Chicago: Freehand Chicago
Set within a classic 1920s building, Freehand Chicago puts you in the heart of the vibrant River North district.
Visitors will be close to the river and Michigan Avenue while enjoying a lively communal atmosphere and an on-site bar. Guests can enjoy the outdoor terrace plus bicycle hire to explore the lakefront.
Best Mid-Range Hotel in Chicago: ACME Hotel
A stay at ACME Hotel places you steps from the shops and entertainment on the Magnificent Mile.
Guests will have access to upscale amenities, on-site dining plus cable TV and a workspace. There is also a cocktail bar, bakery and fitness center.
Best Luxury Hotel in Chicago: The Peninsula
For opulence and comfort, you can’t look past The Peninsula.
Just minutes from Navy Pier and the Riverwalk, guests will enjoy an Asian-inspired spa house, multiple highly rated restaurants and luxurious rooms with unforgettable views.
The hotel also comes with a sun terrace and indoor pool.
DISCLAIMER: Some of the links in this article are affiliate links, which means if you book accommodation, tours or buy a product, we will receive a small commission at no extra cost to you. These commissions help us keep creating more free travel content to help people plan their holidays and adventures. We only recommend the best accommodations, tours and products, and regularly review these. Thanks for your support, kind friend!
Source
