Things to do in Chicago – 13 Amazing Must Sees & Dos

Updated On: April 15, 2024 by   Courtney Augello

Chicago is America’s third-largest city, home to more than 2.7 million people and covers over 600 km². In a city so big, there are endless attractions to visit. 

Things to do in Chicago 

From sports and shopping to local foods and modern art, here’s our list of 13 iconic things to do in Chicago.

1: See the Bean

Officially known as Cloud Gate, the Bean is one of Chicago’s most iconic modern art displays. It was constructed in 2006 by artist Anish Kapoor. 

The design for the Bean was initially created for an art competition. Kapoor based the piece on liquid mercury and was designed to warp the reflection of Chicago’s skyline and the people who stand near it. 

Kapoor’s design won the contest, and the city began planning to build Cloud Gate. At first, some architectural experts said the design wasn’t structurally sound enough to build, but they figured out a way to make it more stable. 

Eventually, the Bean was completed using over 160 sheets of stainless steel welded together. Since its unveiling at Millennium Park in May 2006, Chicagoans and tourists worldwide have flocked to the sculpture. It is a stunning piece to take photos with and is commonly seen on Chicago merchandise. 

If you are hoping to get a good photo with the Bean, arriving early in the morning is best to avoid the crowds. Make sure to take photos from different angles around Cloud Gate to see all the different reflection warps the piece has to offer!

Modern art can be found throughout the city, and visiting the exhibits, including the Bean, are great things to do in Chicago.

2: High-up Thrill-seeking Things to do in Chicago

To get the best view of Chicago, you must climb up some of the city’s tallest skyscrapers. For thrill-seekers, these are 2 of the most exciting things to do in Chicago.

The Willis Tower is Chicago’s tallest skyscraper and the third tallest in the Western Hemisphere. In this building, up 103 floors above the city streets, tourists can take a step out onto the Skydeck: a balcony made completely of glass. It extends about 4 feet outside the Willis Tower and provides amazing views of Chicago from over 1,350 feet in the air.

Also featured in the Willis Tower is a 60-minute experience where you can interact with exhibits showcasing the history of the building. If you’re looking for an exciting and educational experience, visiting the Skybox is one of the most thrilling things to do in Chicago!

Another dare-devilish attraction in the Windy City is Tilt from 360 Chicago at the John Hancock building. This observation deck is a great way to get a unique view of America’s 3rd largest city. 

At just over 1,000 feet above the streets below, Tilt does exactly as it sounds – leans you outwards over the city! Guests hold onto handrails inside the observatory windows as they slowly tilt forward, giving you a perfect view of the Magnificent Mile below. 

This experience lasts between 2-3 minutes and is one of the best things to do in Chicago for anyone brave enough to step out onto the ledge.

3: Eat like a local

Chicago is known for its food: deep-dish pizza, Chicago-style hotdogs, cheddar & caramel popcorn, great Italian beef sandwiches, and more. Checking out local restaurants and getting a bite to eat is a must on our list of top 7 things to do in Chicago.

Pizza

For the best deep-dish pizza, a few restaurants are adored by locals. The first is Lou Malnati’s, which has over 50 locations throughout the city & suburbs. The most iconic part of Lou Malnati’s pizza is their signature crust, which they even trademarked! It is a crispy, buttery base called Buttercrust™. 

Another popular pizza place in Chicago is Giordano’s. They have been feeding Chicagoland since 1974 and offer a wide menu of soups, salads, pasta, sandwiches, and of course – pizza! With a famous cheese pull and flavourful sauce, Giordano’s is a great restaurant to grab a bite in. Visiting these restaurants are considered great things to do in Chicago by locals and tourists alike.

Hotdogs

You’ll find multiple hotdog restaurants, carts, and pop-ups throughout the city and suburbs of Chicago. There are so many different stops available; grabbing a quick hotdog is one of the most popular things to do in Chicago!

Chicago-style hotdogs are unique to any other city’s style. The iconic combo includes an all-beef frankfurter, chopped onions, tomato wedges, pepperoncini, bright green pickle relish, and a kosher dill pickle spear, all served with mustard and celery salt on a poppyseed bun.

Stopping for a hotdog is one of the best things to do in Chicago to embrace the city’s culture!

Italian Beef

A historical part of Chicago’s food scene, Italian beef sandwiches have been around since the 1930s. It was invented by Italian immigrants who served the dish at their weddings and gatherings.

The sandwich is made from wet-roasted sirloin roast beef that is sliced thin and then soaked in beef broth for hours on end. It is typically served with Chicago-style giardiniera or sweet peppers on a French bread roll. Many Chicagoans ask for their bread to be dipped or double-dipped into the beef au jus to add flavour.

The best place to try an Italian Beef sandwich in Chicago is at Al’s Beef, where they’ve been perfecting the recipe since 1938, making it a must-do on our list of things to do in Chicago.

Dessert

On a hot day in the summer months, finding delicious ice cream is one of the most refreshing things to do in Chicago. If you’re looking for a sweet treat, why not try the original rainbow cone? Located on Western Avenue in Chicago, Rainbow Cone first opened in 1926. The original dessert featured ice cream flavours such as chocolate, pistachio strawberry, and orange sherbet, all served together in one cone.

Today, customers can buy ice cream cones, sandwiches, and cakes, along with milkshakes and doughnuts. To grab these frozen treats, you can either visit the storefront or find one of their ice cream trucks driving around the city. Customers can even have Rainbow Cone cater for events like birthday parties.

Whether you’re looking for a meal to fill up on or a quick sweet treat, checking out these local favourites are great things to do in Chicago.

4: Go to a Local Sports Game

With its long history, Chicago sports is a huge tourist attraction for the city. Chicago has teams in each Major League, so sports fans of all kinds will feel welcome. Different sports will be in season depending on the time of year you visit Chicago. 

If you’re visiting in the summer, seeing baseball or soccer games are both fun things to do in Chicago. The Windy City is home to 2 baseball teams: the Cubs and White Sox. If you are lucky, you might catch them facing each other in a Crosstown Classic game! Or, if soccer is more interesting to you, grab tickets to see the Chicago Fire play at Soldier Field.

During the winter months, hockey and basketball are in season. The Chicago Blackhawks have a long history in the city since they are one of the original 6 teams to join the League. The Chicago Bulls are also a very popular team in the Windy City and draw large crowds to every home game. Both teams play from the United Center on W Madison Street, which is lovingly dubbed the Mad House on Madison due to how engaged the fan base is. No matter who you see play, cheering in the Mad House is one of the most exciting things to do in Chicago.

The most popular sport in America, football, is played in the fall season and seeing them play is one of the best things to do in Chicago to embrace America’s sports culture. The Chicago Bears have been a mid-tier team in recent years, despite having the second-most victories of any NFL team. The team was founded in 1920, and their games are played at Soldier Field at Chicago’s Museum Campus. 

No matter which sport you choose to watch, seeing a game is one of the best things to do in Chicago due to the teams’ histories and adoring local fans.

5: Get Hands-On at the Museum of Science & Industry

The Museum of Science & Industry opened its doors in 1933 and is one of the most popular museums in Chicago. It features interactive exhibits focusing on both the past and visions of the future. Due to its unique hands-on displays, it feels more like a science playground than a museum and is one of the most interesting things to do in Chicago.

Coal Mine

One of the MSI’s most famous exhibits is the coal mine. It was the museum’s very first exhibit. At the coal mine display, visitors descend down a mine shaft to Old Ben No. 17, a real coal mine in Southern Illinois that was relocated to the MSI.

 Guests then get to ride on minecarts through the history of coal mining. The mine focuses on the technological advancements made in the mining industry, from the pickaxe to longwall mining. Due to Illinois’ long legacy of coal mining, taking the MSI’s tour through Old Ben No. 17 is one of the greatest things to do in Chicago if you’re interested in the city & state’s history.

Science Storms

At the top of the list of fun things to do in Chicago, Science Storms at the Museum of Science and Industry teaches guests about different forces of nature, such as lightning, avalanches, and even tornados, by replicating them inside the showroom.

Visitors can create a tsunami, experience the electricity of a 20-foot Tesla coil, and join storm chasers as they monitor extreme weather. One of the biggest draws of the Science Storms exhibit is the 40-foot tornado module. At this display, guests can use a control panel to change wind directions and weather conditions to create a vortex. You can even enter the exhibit and stand inside your tornado if you’re brave enough!

U-505 Submarine

On the lower level of the MSI, guests can step inside a real German U-505 submarine. This vessel was captured by Allied forces during WWII and helped them to win the war. The U-505 has been on display in the museum since 1954 and is longer than a city block.

The history behind the submarine’s capture is fascinating – once the Allies located and captured the U-505, they strategically hid it from the Germans to make them think it had sunk. 

Originally, the submarine was docked outside of the museum, but the Chicago Weather began taking its toll. To stop any additional damage, the U-505 was moved inside, and a large exhibit was built around it. The submarine was moved with remote-controlled dollies at a speed of 2.5 centimetres per minute. 

If you take the guided tour through the submarine, you can get a first-hand look at the inner workings of the vessel. This includes wartime technology found aboard, the tiny galley and meeting areas, and even the bunk beds where soldiers slept. 

In addition to the submarine, this exhibit also takes guests back to the 1940s with news clippings, videos, and photographs from the war. The pieces focus on Hitler’s rise to power, the drafts and enlistment from the United States, and how U-Boats prevented the Allies from getting important supplies across the Atlantic.

If you’re intrigued by WWII history, this section of the museum is one of the best things to do in Chicago.

Seasonal Displays

Although visiting the MSI’s mainstay exhibits are amazing things to do in Chicago, the museum also features incredible seasonal displays. These exhibits are typically available for a few weeks at a time and draw in crowds from all over the world. Even though they sometimes charge a bit extra to see these exhibits, these displays are always worth it.

These displays can range from the history of animation for Disney or Peanuts to a tour of Lego’s amazing legacy. If you want to see a temporary exhibit, check the MSI’s website to see when they are available.

6: Check out Navy Pier

Walking through Navy Pier is one of the most popular things to do in Chicago. The pier opened in 1916 and is open all year round for guests.

Navy Pier’s biggest attraction is the Centennial Wheel – a Ferris wheel open all year and sports climate-controlled gondolas for guests. At over 200 feet tall, this landmark is an iconic part of Chicago’s Skyline and gives visitors an amazing view of the city.

The pier also hosts a variety of other attractions, including a beer garden, the Chicago Children’s Museum & Shakespeare Theatre, bike tours, souvenir shops, and restaurants. Watching fireworks from Navy Pier over Lake Michigan is one of the best things to do in Chicago if you are in the Windy City for the 4th of July or New Year’s.

7: Shop til you Drop on the Magnificent Mile

One of the most famous shopping areas in the world, the Magnificent Mile is home to over 450 stores. The Magnificent Mile is only 1 mile from Navy Pier, making it one of the best things to do in Chicago during a day out.

At the end of the Mag Mile is Water Tower Place, a vertical shopping mall that covers 8 levels and has over 100 stores. It was the first-ever mixed-use development in America, hosting a shopping mall, apartments, a theatre, and a hotel. 

While The Mag Mile features an array of luxury storefronts, restaurants, and hotels, Water Tower Place is known for shifting the economic sway from high to middle class by introducing casual retail stores such as Lego.

If you are looking to bulk up your wardrobe or just window shop, taking a stroll down the Magnificent Mile is one of the most fun things to do in Chicago.

8: Check out Chicago’s Museum District

Chicago is home to multiple museums that help to put the city on the map. These places take guests through the past, the future, the oceans, and even the cosmos. Strolling through Chicago’s Museums is a must on our list of things to do in Chicago.

Field Museum of Natural History

Chicago’s museum of natural history dates back to the 1893 World’s Columbian Exposition. There were ever 65,000 exhibits of cultural and natural artefacts at this fair. After the exposition, local merchant Marshall Field donated $1 million to fund the museum’s creation. The museum was opened the following year.

Today, the Field Museum is home to 40 million artefacts and is one of the biggest history museums in the world. These pieces include gemstones, fossils, meteorites, and ancient cultural artefacts. The museum also features a library that contains over 250,000 books.

The museum hosts research into the specimens they showcase and helps to protect and preserve fossils and other artefacts. In fact, the Field Museum has some of the largest collections on the planet, including one of the largest fish collections worldwide. The museum’s mission is to keep these pieces of history safe, educate the next generation of scientists, and protect valuable ecosystems across the world.

The Field Museum’s most famous artefact is Sue the tyrannosaurus rex. The fossil is named after Sue Hendrickson, who discovered it in South Dakota in August of 1990. Sue is one of the best-preserved and largest T.Rex specimens ever discovered, with over 90% of her bones preserved. Sue is over 12 metres long and over 4 metres tall. Her exhibit was opened to the public in May of 2000.

Besides Sue, the Field Museum has several other permanent exhibits. Of these is the Animal Hall, where guests can walk through different habitats and see how animals from all over the world survive. Another fascinating exhibit is Inside Ancient Egypt. This area features a 3-storey replica pyramid and 20 human mummies.

Shedd Aquarium

The Shedd Aquarium was donated to Chicago by John Shedd, a merchant who Marshall Field mentored. The aquarium cost over $3 million dollars to fund and opened in May of 1930. The Shedd is one of the most visited aquariums in the world, making it one of the best things to do in Chicago.

Today, the Shedd Aquarium is one of the biggest aquariums in the world and is listed on the National Register of Historic Places. The Shedd welcomes over 2 million visitors every year through their doors. Besides entertaining guests with sea life exhibits and shows, the aquarium also helps animals around the globe. It helps rehabilitate and rescue wildlife, protect endangered species, and promotes education for the next generations about protecting our oceans.

The Shedd Aquarium features multiple exhibits for visitors to observe. The Waters of the World exhibit features sea creatures from rivers, islands, lakes, and oceans globally. Also featured here are creatures from Chicago’s local waters. 

The Carribean Reef exhibit is the most popular part of the Shedd Aquarium. Here, a diver interacts with the animals while speaking to a crowd of visitors. It was one of the first exhibits created at the Shedd. Other exhibits include the Stingray Touch, where guests can place their hands into the tank and pet the rays as they swim.

The most popular show at the Shedd Aquarium is the dolphin show. Here, trainers get into the large tank with the dolphins and instruct them to do various tricks and jumps. Throughout the show, the staff give guests an insight into how the dolphins are trained and cared for.

As guests sit in the audience, some may be in the “Splash Zone”, where the dolphins splash their tails and spray water into the seating area. In addition to dolphins, penguins are also commonly seen during this tour. They are free to wander around the stage and often parade through the audience.

For endless aquatic adventures in the Windy City, visiting the Shedd Aquarium is one of the most fun and educational things to do in Chicago.

Adler Planetarium

The Adler Planetarium was the first planetarium to open in the United States and the twentieth in the world. It was founded by Max Adler, a businessman local to Chicago and opened in May of 1930. Like the Shedd Aquarium, the Adler Planetarium was added to the list of National Historic Landmarks.

At the planetarium, astronomists work to research outer space both for the scientific community and the general public. The aim of the Adler Planetarium is to educate and inspire the exploration of our universe.

When visiting the planetarium, guests can walk through the research halls and enter the three domed theatres on the site. Here, guides show guests how the theatres work and let them look closer at the stars and planets in our sky. The Adler Planetarium also hosts Adler After Dark, a 21+ event hosted in the evening and consistently regarded as one of the best things to do in Chicago for a date night. Family evening events, such as Adler Planetarium’s Astro Overnights, are also available, where you can sleep at the museum and get a great view of the night sky.

McCormick Place

McCormick Place is the largest convention centre in North America. Robert McCormick began planning the centre in 1927, and it opened to the public in November of 1960.

McCormick Place is more than just a convention centre. Guests who visit the centre can eat, sleep, and find entertainment throughout the four interconnected buildings of the centre. In addition to over 2.5 million square feet of convention space, McCormick Place has a basketball court for games & concerts, a theatre, over 2,500 guest rooms, and multiple restaurants.

McCormick Place welcomes over 3 million guests annually and hosts some of the most popular conventions, including the Chicago Auto Show and International Technology and Manufacturing Show. If you are visiting Chicago for a convention, McCormick Place is a spectacular venue and central to the rest of the city.

If you’re looking for fascinating things to do in Chicago, look no further than the city’s museum district. Within the museums, you can step into the past, launch into the future, dive deep into the ocean, or gaze among the stars. If you plan to visit more than one museum on this list, you can purchase a City Pass, which lowers the admission prices to the museums.

9: Visit the free Lincoln Park Zoo

Lincoln Park Zoo was founded in 1868 and has been free for guests for over 150 years. It is the fourth oldest zoo in the United States and is home to over 1,000 animals. Since there is no entrance fee for the zoo, visiting is one of the best free things to do in Chicago.

Lincoln Park Zoo is dedicated to researching, rescuing, and rehabilitating animals. In fact, the first American bison born in captivity was born there after the species was almost hunted to extinction in the 1880s. The Zoo aims to educate the public about the importance of protecting endangered species. Since the Zoo runs mostly on donations, everyone can access the grounds and the learning experiences they provide.

Even though Lincon Park Zoo is free to enter, there is no shortage of exotic animals there. The zoo is home to lions, penguins, bears, and pythons. Also on exhibit are beavers, camels, axolotls, red pandas, and more. The zoo even has a petting farm area where guests can meet pigs, cows, horses, and other domesticated animals. The cows in this area are milked in public, and experts are always available to answer questions about farm life.

In Chicago, not many attractions are free, especially of this quality. Visiting Lincoln Park Zoo is one of the cheapest and most fun things to do in Chicago for a day out.

10: Take an Architecture Tour

Chicago’s skyline is famous worldwide. The city features gothic architecture, art deco, and modern skyscrapers that combine the past and present. Learning about the history of some of Windy City’s most iconic buildings is one of the best things to do in Chicago on a warm afternoon.

The architecture tours in Chicago take you by boat down the Chicago River. As you go through the city, your tour guide will tell you about the buildings’ pasts and design inspiration. While aboard, you’ll hear stories about more than 50 of the city’s historic buildings and how Chicago grew from a small town to the third-largest city in America.

The architecture tours are a beloved attraction in Chicago and were voted the best boat tour in North America in 2021. From learning about history and architecture to simply enjoying a 90-minute cruise on the river, there’s something on this tour for everyone.

11: Walk Through the Chicago Art Institute

The Art Institute of Chicago is one of the largest and oldest art museums in the world. With its expansive collection of art pieces, touring its exhibits is one of the best things to do in Chicago for art lovers.

The Institute was founded in 1879, but its history goes back even further. In 1866, a group of artists created the Chicago Academy of Design, a free school with an art gallery. Unfortunately, the Great Chicago Fire destroyed the academy buildings in 1871, and the artists went into debt. The artists tried to restore the academy but were unsuccessful. 

In 1879, some of the original group of artists set out to create a new academy called the Chicago Academy of Fine Arts. Later, in 1882, the organisation changed its name to the Art Institute of Chicago.

The Institute’s mission is to collect & preserve art pieces from all over the world and to promote conversation and understanding of the interpretations of the art pieces. The Institute also uses its collections to promote equity racially and in other forms. They are open about art pieces from different cultures and time periods and work hard to acknowledge that the museum sits upon traditional Native American lands.

Today, the Art Institute of Chicago hosts over 300,000 works of art and welcomes more than 1.5 million visitors annually. In addition to the exhibits, the Institute also features multiple conservation laboratories, a conservation science department, and Ryerson and Burnham Libraries, two of the largest architecture and art history libraries in the country. With these additions, the museum is now the second-largest art museum in the United States of America.

The art within the museum covers over 5,000 years of human history. These pieces come from different cultures and include early Japanese works and modern American art. The art displayed is also in different forms, such as prints, paintings, ceramics, jewellery, and clothing.

From American artists, some of the most famous works of art in the museum include  American Gothic and Nighthawks. Both of these paintings are from just after the Great Depression and are symbolic of American life during the time.

There are numerous famous European pieces on display as well. Two of the most recognisable works are Sunday Afternoon on La Grande Jatte from 1884 and Vincent van Gogh’s Self Portrait. 

Besides art pieces, the Art Institute of Chicago is also home to more than 130,000 architectural drawings and models, some of which date back to the 1870s. These pieces are works by Frank Lloyd Wright and Ludwig Mies van der Rohe, who called Chicago their home.

With a variety of works, cultures, and histories on display, walking through the Art Institute of Chicago is one of the most fascinating things to do in Chicago. One of the benefits of the museum is that you can visit rain or shine, so it is a perfect way to brighten for a cold or cloudy day.

12: Go Back in Time on a Gangster Tour

During the Prohibition era in the United States, Chicago had a huge gangster scene. Members would produce and sell illegal alcohol and take part in other criminal activities such as loansharking, gambling, extortion, and even murder. If you want to feel what it was like to be a gangster, taking a guided tour through the city is one of the most interesting things to do in Chicago.

The most infamous gangsters during this time were part of the Chicago Outfit, a group of Italian-American gangsters based in the city’s South Side. This gang was at its height during prohibition but still operates in the city today.

The leader of the Chicago Outfit was Al Capone, also known as Scarface. Capone was the Outfit’s co-founder and became more violent as his power within the group grew. 

Even though he participated in criminal activity, Capone had a relationship with the Chicago Police Department and was safe from their prosecution. Similarly, many Chicagoans at the time thought of him as a Robin Hood-like figure because he donated large sums of money to local charities.

The Chicago Outfit’s negative reputation erupted after the Saint Valentine’s Day Massacre that Capone had organised. At this point, he became recognised as a public enemy, and the FBI were determined to arrest him. He was convicted of tax fraud in 1931 and died 16 years later. Al Capone is buried at Mount Carmel Cemetery just outside Chicago, and tourists often visit his extravagant grave site.

On Chicago’s gangster tours, you can relive some of the Chicago Outfit’s most iconic moments and learn about Chicago’s darker side. These tours have been given in Chicago for over 30 years and are a great addition to your bucket list.

Tours are offered both by walking through the city and by bus. They take you to some of the gang’s hideouts and favourite restaurants and bars. If you choose a walking tour, you can access some of the speakeasies where Capone sold alcohol during the prohibition and underground tunnels that the Chicago Outfit used.

If you want an even grimmer experience, choose a nighttime gangster tour. During the evenings, the guides take you to the infamous Biograph Theater and the site of the Saint Valentine’s Day Massacre.

For a deeper, darker look at the glamorous Windy City, the Chicago gangster tours are a must on our list of best things to do in Chicago.

13: Enjoy the Local Waters

If you are visiting during the summer months, hanging out by the water is one of the most fun things to do in Chicago!

Kayaking groups have paddled in Chicago waters since 1999. Guided tours are available on the Chicago River and Lake Michigan for visitors to learn more about the city and its architecture. 

On Wednesday and Saturday nights, groups Kayak down the river towards the lake to watch the Navy Pier fireworks from the water. With stunning shows up above and reflections in the water, it is a great event for date nights.

Also held at night, the city lights tours take kayakers through Chicago to admire the buildings as the lights reflect off the water. If you’re more into nature than architecture, sunset tours are also available. These take guests through the river to its mouth or out on Lake Michigan, where the sunset is visible on the horizon. Both of these tours are perfect for a relaxing wind down to the day.

For warm days, relaxing on one of the lakefront beaches is a perfect thing to do in Chicago. These sandy oases are popular with locals and tourists alike. The beaches are great places to play volleyball, chat with friends, tan, and grab a drink at the bars. 

There is no admission fee to access the beaches, and they are very close to other attractions like Navy Pier and Lincoln Park Zoo. Lifeguards are on duty daily to allow for swimming in the Lake, and they are good places to spend a relaxing day with family or children. For a chill day in the Windy City, heading to the beach is one of the best things to do in Chicago.

There’s an endless amount of things to do in Chicago!

From shopping on the Magnificent Mile to seeing the Windy City from 103 stories up, there are many fun things to do in Chicago. The city is always bustling with friendly people, amazing restaurants, and tons of entertainment to keep you busy.

If you plan to visit the Windy City, take in as much of its fascinating history and attractions as possible. Whether you tick one or two items off this list or squeeze in all 13, these incredible things to do in Chicago will make your trip memorable.

If you want to experience these things to do in Chicago, check out these USA Travel Statistics Before You Go.