An Insider's Guide to the 20+ Best Things to do in Chicago

Last Updated on 25th January 2024 by Sophie Nadeau

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Chicago city is a cultural hub with magnificent architecture, vast green spaces and a sparkling lake. This city truly has so much to uncover which is why you’ll want to read on and get to know more… So read on to discover the best things to do in Chicago.

Located on Lake Michigan, the city of Chicago is the third largest city in the United States, with a population of nearly 3 million people. However, with that size, it can be hard to figure out the best attractions on offer and what to miss (which is what this guide is for!)

What is Chicago known for?

The vibrant city of Chicago is most famous for its magnificent architecture, rich with history and bursting with a thriving culture, the city is sure to steal your heart.

Chicago is also home to a legendary jazz scene, what better place to go dance the night away than the hustle and bustle of this gorgeous city that captivates all who visit it!

Getting around Chicago

There are a few different ways to get around Chicago and what you choose will depend on how you like to see a city and your budget. For the most part, the easiest way to get around is by the local bus system.

For a cool experience, you can also consider the trains, which are sometimes elevated above the ground and below ground in places. Another option to see all of the sights in one go is to:

If you’re looking to discover the area with a local guide, here are some walking tours (just make sure to wear comfortable shoes as you’ll be on your feet for at least an hour or so during these tours):

Tiffany Art Glass Works Walking Tour – This tour will take you on a stroll of Chicago to learn more about Louis Comfort Tiffany and discover some of his most famous works.
Downtown Architectural Interiors Tour – Together with a local guide you’ll walk around downtown Chicago and discover some of the more interesting architectural gems of the city.
Downtown TV and Movie Sites Walking Tour – This tour is a must-see for movie buffs and you’ll discover 30 filming locations including where Ferris Bueller’s Day Off to The Untouchables to The Dark Knight were filmed.
Art Deco Skyscrapers Walking Tour – If you’re into Art-deco architecture, then you’re in for a treat. This tour will showcase many of the most magnificent and lavish buildings in the city.

20+ Best things to do in Chicago

Chicago is abundant with sights to behold and attractions to be amazed by, a city where visitors are easily drawn in to its wonder. If you’re looking for a romantic US getaway, then Chicago also makes for a perfect weekend escape.

Because there is so much to see and do when visiting, this can also make it quite overwhelming, which is why we’ve put together some of the best things to do in Chicago, so that when you can make the most of it when visiting this dreamy destination.

Millennium Park

One of the most iconic sights in all of Chicago is that of Cloud Gate, better known as “The Bean“. This monumental artwork (by Anish Kapoor) is one of the largest permanent outdoor installations in the world and a must-see when visiting the city!

Reflecting the city’s famous skyline and the green expanse of the surrounding park since 2006, this impressive sculpture now has an interactive AI assist feature that can help visitor plan their trip in Chicago, suggesting new places or directions of where to go!

Aside from talking to The Bean for travel tips of the city, the Millennium Park itself is a gorgeous spot to spend the afternoon with a picnic, or simply just strolling through and people watching.

Another famous sculpture by Jaume Plensa (Crown Fountain, 2004) sits close to the street level and is an interactive fountain, perfect during the Summer months for visitors of the park to cool off and splash about in the water.

Millenium Park’s hidden treasure is Lurie Garde. This beautiful spectacle of botanical landscaping offers tranquil respite from the hustle and bustle of the city, for both its people and wildlife.

The park is over a whopping 20 acres and there’s a lot to see, so here are a few other top suggestions to consider when visiting:

Explore the Play Garden, a kid’s fantasyland! filled with structures to explore, a 40 ft climbing wall and a mini-golf course
Go skating along the Skating Ribbon, In Summer (also in Maggie Daley Park area) the curved ribbon around the climbing wall becomes a rollerblading spot, and in Winter it’s iceskating
Enjoy an event, whether it’s music, a film screening or a festival, there are numerous events throughout the year so be sure to check online so you don’t miss out!
Grab a bite to eat, if you’re all tired out from the fresh air, there are plenty of restaurants nearby

Millennium Park itself is within another park, Granton Park, making it a vast area to explore and discover you could probably spend up to a day here!

Grant Park and Buckingham Fountain

The crown jewel of Grant Park is the spectacular landmark, Buckingham Fountain. Inspired by one of the ornate fountains of the Palace of Versailles in France, this is one of the largest fountains in the world!

The fountain was commissioned by Kate Sturges Buckingham as a memorial for her brother Clarence, and opened to the public in 1927. Grand both in its size and intricate stonework, this mesmerising water artwork stands 7m high.

Active from May through through to mid-October, this beautiful attraction puts on quite the display! During the day visitors can enjoy a 20 minute spectacle of water shooting 150 ft into the sky, but at night the fountain comes to life. A dazzling water display with warming lights and music takes place on the hour, every hour after dusk.

Grant Park isn’t short of things to discover, practically an open-air art gallery, the park is home to many fabulous sculptures. Some of the must-see artworks of Grant Park while strolling through:

Fountain of the Great Lakes,
Agora, (by Magdalena Abakanowicz
The Bowman & The Spearman (two bronze equestrian sculptures standing as gatekeepers in Congress Plaza)

Maggie Daley Ice Skating Ribbon

As briefly mentioned just before, you can find the Skating Ribbon in Maggie Daley Park.

Throughout the warmer months people skate, scooter or rollerblade along the quarter mile stretch of the Skating Ribbon, enjoying the fresh air beneath city skyline and shade of the surrounding trees.

However during the Winter months (usually from November to March), the curved ribbon turns into a popular ice-skating spot, which attracts visitors from all over to enjoy the unique experience in downtown Chicago.

Ice skating is free Monday -Thursday and for a small fee you can book tickets for slots Friday-Sunday, it’s recommended you do this online in advance to ensure there are enough skates to rent.

The Chicago Riverwalk

Those who are looking to partake in one of the top activities in Chicago would do well to head along the Chicago Riverwalk. As its name would suggest, this unique public space is located on the Chicago River Bank.

What makes the walkway so unusual is that it lies in the shadow of skyscrapers, among other Chicago landmarks. Free to wander along, a walk along the river will guarantee you the chance to visit several open-air restaurants and marvel at the architecture that the city is so well-known for.

The Magnificent Mile

Also known as the “Mag Mile” this impressive and vibrant area is full of architectural gems to discover, and is one of the world’s most iconic shopping districts!

The Magnificent Mile encompasses a 13-block stretch of North Michigan Avenue, running from the banks of the Chicago River to the south, to Oak Street to the north and extends onto the city’s scenic Lake Chicago.

Boasting of high end fashion, luxury brands and boutiques the Mag Mile is loaded with things to explore and places to fine dine in, it’s probably one of the most affluent sections of Chicago city. But don’t be intimidated by this fact, as there’s still lots to see in the area aside from its shopping.

The best way to soak in the bustling atmosphere is simply to stroll along and see where it takes you! Whether its tasting the flavours of Chicago, shopping for something special or admiring the historical architecture and wandering along the lakefront.

A few buildings you won’t want to miss:

Tribune Tower, a neo-Gothic skyscraper built in 1925
The Wrigley Building, inspired by a cathedral in Seville, Spain this skyscraper has a soaring clock tower and is best viewed when illuminated by lights at night
333 N Michigan Avenue, a skyscraper in art deco style
Water Tower and Pumping Station, an iconic symbol of North Michigan Avenue
Woman’s Athletic Club, the first athletic club for women in the United States, founded in 1898

As you can imagine, the district comes to life at night with the warming kaleidoscope of shimmering lights as the tall skyscraper loom above and the warm buzz of car lights drive past. Sipping a drink sat in one of the local bars is definitely a must!

If you happen to be in Chicago during mid-late November you can go to the Magnificent Mile Lights Festival where a magical celebration of lighting the Christmas tree takes place, with fireworks and a dazzling parade of festive cheer.

Navy Pier

Located in the northern side of Chicago, on the shoreline of Lake Michigan, lies the Navy Pier. Stretching over a mile and a half long, there’s plenty to keep you buys on this waterside treasure!

is free and open to the public all year round, hosting an array of events and public programs, the pier is a buzzing hub of culture and excitement, making it a great experience to anyone who visits.

Abundant with restaurants, bars and attractions, and hosting an array of events and public programs throughout the year. The pier is open to the public all year round and is a buzzing hub of culture and excitement, making it a great experience to all those who visit.

Discover the history of Chicago’s iconic Centennial Wheel, and take in the views of the city skyline from up above!

Navy Pier is the perfect spot to spend an evening, whether its grabbing a bite to eat, sipping a drink with a view or dancing to live jazz as the sky lights up the night with dazzling fireworks.

360 Chicago Observation Deck

For one of the best views of Chicago, you most definitely should head to 360 Chicago (formerly known as the John Hancock Observatory) where for a fee you can visit the observatory on the 94th floor and be greeted by stunning views of Downtown Chicago and its surrounding neighbourhoods.

An optional add-on to your visit (if the thought of heights and thrill seeking is your thing) is to try Chicago’s highest attraction TILT. Offering epic views of Chicago from a completely different perspective, tilted in an enclosed, glass and steel moveable platform with a downward-facing view. This attraction just further highlights Chicago as a pioneer in architecture.

The best time to visit 360 Chicago is definitely at night, where the hustle and bustle of the city comes to life with the glow of a thousand colours! Purchase your 360 Chicago Observation Deck Sip and View Ticket here in advance.

Museum of Science and Industry

One of the largest museums in the United States and home to hundreds of exhibits, awe-inspiring artefacts and interactive activities, the MSI is brings the fascinating worlds of science, technology, and engineering to life!

Located south of Downtown Chicago, the MSI is housed in the beautiful building the Palace of Fine Arts and is open every day of the week 9:30am-4pm.

What better way to start your day than spending the morning getting curious? The museum is vast in size, so here are just a few museum favourites of the things you can see:

U-505 Submarine, World War II German submarine (one of only five left in the world!)
ToyMaker 3000, where you can watch robots assemble custom toy tops!
Science Storms, an interactive exhibit where visitors can step into a 40-foot vortex of vapor and feel the full forces of natural phenomenons
Baby Chick Hatchery, learn about genetics and DNA in real time

Take a Chicago Architecture River Cruise

The best way to truly experience the captivating architecture of Chicago city is by boat, and there are several options you can choose depending on your budget and preference.

Usually lasting around 90 minutes, on the River Cruise and you will be shared the fascinating history of over 50 buildings along the Chicago River and a knowledgable overview of the city’s architecture from experts who know.

The tour is now also offered in the evening, the architecture of course takes on a whole different life when lit up by the soft golden glow of lights at night, the perfect romantic setting for a date night.

Although a little on the pricier side, just the sheer amount of historical insight, as well as the spectacular views make the tour well worth it! Here are some of the river cruises you can book in advance:

Art Institute of Chicago

The prestigious Art Institute of Chicago, founded in 1879, is one of the oldest and largest art museums in the United States and home to some of the finest artworks in the world!

Located downtown just by Millennium Park you can discover a world of art and resources from all corners of the globe and immerse yourself in the wonders of this museum’s collection.

A few stand-out artworks from the permanent collection that you won’t want to miss:

The bedroom, 1889 – Vincent van Gogh
Water Lillies, 1906 – Claude Monet
The Crucifixion, 1627 – Francisco de Zurbarán
Nighthawks, 1942 – Edward Hopper
American Gothic, 1930 – Grant Wood

Adler Planetarium

America’s first planetarium, inspiring the next generation of space explorers!

This public museum is dedicated to the world of astronomy and astrophysics was founded in 1930. Even if the inside of the museum itself doesn’t interest you, the impressive Art Deco style building and its copper clad dome depicting the signs of the zodiac, are not ones to miss.

Escape to the stars! A highlight of visiting the planetarium is the various ‘Sky Shows’ where you can observe depictions of the universe under the iconic dome theatres and learn more in depth about what lies beyond planet Earth.

Perfect for a rainy day! Adler Planetarium is open late night on Wednesdays (till 10pm) and closed Tuesday’s & Thursday’s.

The Field Museum

Yet another museum worth checking out when in Chicago is that of The Field Museum of Natural History.

A history of history, this educational museum is filled with exhibitions of everything from skeletons, fossils, to interactive experiences and is the perfect place to spend your morning or afternoon strolling around.

A popular highlight for many visitors of The Field is SUE the T.Rex (specimen FMNH PR 2081), at more than 40ft long and 13ft tall SUE is physically the largest Tyrannosaurus rex specimen discovered! You can buy your Field Museum Ticket ticket here in advance.

Museum of Contemporary Art

If there’s one thing you should know about Chicago, it’s that (aside from the Louvre) its Museum of Contemporary Art houses the largest collection of Impressionist and post-Impressionist art on the planet!

The museum is a place where new ideas are shown and tested, hailed for its innovative way of thinking where art can be so much more of an experience for both artists and viewers, you can enjoy the huge collection of art in all forms of media.

There’s also a lot of art which you don’t need to buy a ticket to see, you can explore spaces like the Sculpture Garden, the Atrium, the Street, and a couple more places all for free!

Museum of Contemporary Art — *You have to photograph this beautiful Koi fishpond at the bottom of the stairs in the museum!*

Skydeck Chicago

Yet another location in Chicago where you can catch a glimpse of the city from above is at Skydeck Chicago, located in the Willis Tower. Purchase your Willis Tower Skydeck and The Ledge Ticket here in advance.

Of all the viewpoints in Chicago this is definitely the highest. Standing in clear observation boxes located on the 103rd floor, visitors can enjoy views of the city spanning up to four states and on a clear day up to a stretch of 50 miles!

If you aren’t scared of heights then this is an absolute must visit experience! It’s definitely recommended to book in advance and for a fee you get a 30 minute period up with the view- not to mention incredible photographs and unforgettable memories.

North Avenue Beach

Those who wish to relax on the beach would be well served by heading to Chicago’s most popular strand of sand, North Avenue Beach.

Swimming with Chicago’s skyline as a view, there are also plenty of bars and restaurants dotted along the boardwalk for you to grab a bite to eat or a refreshing drink. Giving Southern California sunshine vibes, this is the perfect spot to spend a lazy afternoon soaking up the sunshine!

It’s worth noting that swimming is only permitted when a lifeguard is on duty and during the beach season, so keep this in mind when visiting. All of the relevant information can be found of the official Chicago Park District website.

The Chicago Theatre

If you want to visit some of the prettiest architecture in Chicago, then look no further than the legendary venue in the heart of the city, The Chicago Theatre!

This stunning landmark is an “unofficial emblem of the city” as it appears so frequently in film, art and photography of the city, designed by the well-known movie moguls Bablan & Katz.

The inside of Chicago Theatre is elegant and grand, with an elaborate staircase that was patterned after that of the Paris Opera House, and beautifully painted murals covering the ceilings by artist Louis Grell- it’s hard not to feel as if you are featuring in a movie yourself.

Today you can enjoy concerts and touring Broadway shows at the theatre, and if you get a chance to see one, the experience of watching live entertainment in this building is truly something to behold and will be like no other! If you want to discover more behind the scenes of the workings of the theatre, book The Chicago Theatre Tour Experience.

Maggie Daley Park

The Maggie Daley Park is open daily from 6am-10pm and as mentioned earlier, its plentiful with things to do!

Explore and enjoy the wonders of activities and spots within Maggie Daley Park, we’ve listed a few of the top spots which you can find out more about on their official website.

Things to do & see:

Climbing Wall
Enjoy a picnic in the Picnic Groves
Rollerblade or scooter around the Skate Ribbon
Visit the beautiful Cancer Survivors Garden
Explore the Play Garden

Chicago Cultural Center

If beautiful and ornate interiors are your thing, then you’ve come to the right place. This Chicago landmark is and architectural wonder and is home to two absolutely stunning domes.

The building was opened in 1897 as the city’s official reception venue, where the Mayor of Chicago has welcomed presidents, royalty, diplomats, and community leaders.

Now this free cultural centre stands as one of the city’s most popular attractions where visitors can explore art exhibitions, catch cool events or take a guided tour to learn about the magnificent architecture and its history.

Inside Preston Bradley’s Hall, visitors can look up to the Tiffany Dome, a beautiful and intricate stained glass design of over 30,000 individual pieces of glass cut in the shape of fish scales.

The Tiffany Dome’s smaller counterpart is no less beautiful, found in center’s rotunda in the Grand Army of the Republic Hall, you can gaze up to another gem of architecture.

The Chicago Cultural Center is an absolute must when visiting the city, not to mention that it’s completely free both to visit and to take a guided tour!

The Richard H Driehaus Museum

You may be thinking, who is Richard H Driehaus? Well, he was an American businessman, investor, and philanthropist, with a passion for arts and culture, hence why there’s a museum of his collections.

Driehaus wanted to share with the public the beauty of great works of art, architecture and design in hope to inspire and bring joy to the hearts of the people!

Showcasing art from predominantly the late 19th century to the present, with an emphasis on the Gilded Age. Walk-ins for the museum are always welcome so you can purchase on the day and the museum is open every day except for Tuesday’s.

Take a food tour

If there’s one thing that Chicago is pretty famous for, it’s the foodie scene. The most famous item on the menu is probably the Chicago-style-pizza, which is a deep dish or stuffed crust pizza pie. If you want to delve deeper into the culinary side of the city, then you could consider booking a food tour:

Downtown Pizza Guided Walking Tour with Tastings – Sample Chicago’s most famous tasty treat in this walking tour.
Favorite Foods Guided Walking Tour – This walking tour will take you on a culinary experience that includes seeing some of Chicago’s most famous locations, as well as tasting local goodies like pizza, hot dogs, and brownies.
Downtown Donut Tour with Tastings – If you have more of a sweet tooth, then this tour will allow you to sample donut styles like glazed, cream-filled, and more.
Taste of Chinatown Food Walking Tour – Learn about Chinese culture by embarking on this culinary tour which sees you stop at five different restaurants.

See a game!

Of course, when you’re going to a big city, then seeing a sports game is a popular option for many sports fans. Some tickets that you can buy in advance include a Chicago Blackhawks NHL Game Ticket at United Center and a Chicago Bulls Basketball Game Ticket.

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An Insider’s Guide to the 20+ Best Things to do in Chicago

What is Chicago known for?

Getting around Chicago