15 Best Things to Do in Chicago
chicago skyline
Visit Chicago: The Windy City

Chicago is one of those cities that truly has it all — from world-class museums and seemingly endless free events to fantastic shopping districts and vibrant nightlife venues, there's something amazing to do here at any hour of the day or night. 

The Windy City, located inland in the Midwest, is vying for the title of the best American tourist destination. Every year, around 57.6 million tourists visit Chicago, and with such a broad choice of attractions, there is an itinerary suitable for every one of them. 

Whether you’re planning a family vacation or a quick visit, Red Roof has got you covered. We’ve put together a list of the best things to do in Chicago — and there’s plenty more where that came from! If you enjoy good food, sightseeing, and checking out famous attractions — all conveniently located near our budget-friendly hotels — then you’ll find out there’s no shortage of fun things to do in Chicago!

navy pier
Spend a Leisurely Afternoon at Navy Pier

Navy Pier, Chicago's iconic lakefront location, is home to renowned restaurants, shopping possibilities, boat cruises, and much more. This waterfront facility was originally intended to be only a freight port, but it has progressively evolved over the last century to become a must-see destination with exhibits, rides, parks, and incomparable views of the shimmering Lake Michigan. Purchase the Explorer Pass for admission to the Navy Pier's attractions and another 25 attractions and activities in Chicago.

chicago river boat tour
Take a River or Lake Cruise

You can kick back and enjoy Chicago's metropolis from the shores of Lake Michigan and the Chicago River. There are numerous cruises offered, ranging from relaxing lake tours to thrilling speedboat rides. Catch a dinner cruise to watch the skyline transform right in front of your eyes, as the last beams of sunshine transition to sparkly window light peeking through the unique architecture. 

delicious eats
Go on a Food Tour

If you're looking for large servings and robust flavors, Chicago is the place to be. Deep-dish pizza, Italian beef sandwiches, hot dogs piled high with seven toppings, brownies, and beer are just some of the staples. If you want to explore local restaurants that may go unnoticed by out-of-towners, there are a variety of tours for hungry tourists. The Secret Food Tour provides access to these previously unknown venues. You may also take a Tasting Tour of Chinatown on foot, a Bike Tour of Polish pierogis and Mexican tortas, or a 2.5-Hour Walking Tour of the best Chicago pizzas, craft beer and hot dogs.

Discover the Real Chicago via Urban Art

Illinois' largest city is bursting with urban art; travel off the main path with a one-of-a-kind tour that avoids the crowds and explores the underworld and backstreets. Guides not only take you to the city's best murals but they also explain their meanings and history. 

art museum
Soak in the Art

The beautiful Art Institute of Chicago is located in Grant Park. This remarkable institution, founded in 1879, is one of the oldest (and largest) art museums in the United States! There are over 300,000 different artifacts to see, so plan on spending a few hours (or days) seeing them all. If you enjoy art, this is one of the top things to do in Chicago. 

the bean chicago millennium park
Visit Millennium Park and The Bean

Millennium Park, located only a block from Lake Michigan in the center of downtown Chicago, features world-class art, music, architecture, and landscape design. The 24.5-acre park, is one of Chicago's most popular locations, attracting 25 million visitors every year. Don't miss The Crown Fountain, which combines technology and waterpark-style enjoyment! Stroll down the Chase Promenade toward the big bean, which is technically known as Cloud Gate. Cloud Gate is not only beautiful to look at but has also become a symbol of Chicago.

Chicago skyline
See the City From the 360 Chicago Observation Deck

The 360 Chicago Observation Deck, located on the 94th story of the John Hancock Center, provides amazing views of the city's packed cityscape (including the Willis Tower) and the dazzling lake Michigan below. All four neighboring states are visible from the 1,030-foot-high viewing platform (Illinois, Wisconsin, Indiana, and Michigan).Step outside onto the exhilarating tilting platform (TILT) where you can soar high above the city on a glass panel sprawled like Superman, then relax at the bar and enjoy the sunset.

Visit the World’s Largest Indoor Aquarium

An aquarium may not be the first thing that comes to mind when considering things to do in a major world metropolis, but Chicago's Shedd Aquarium should not be overlooked! It is the world's largest indoor aquarium, with approximately 8000 aquatic creatures. 

Willis Tower
Walk the Willis Tower Ledge

The Willis Tower, once known as the Sears Tower (and still commonly referred to as such), is another prominent skyscraper in downtown Chicago. This 108-story building, which stands at 1,451 feet (442 meters) tall, is officially Chicago's highest and offers spectacular views from the top. The observation deck in the Willis Tower, known as the Skydeck, has The Ledge, a terrifying glass ledge and box that you can stand in to watch the city below. 

Tuck Into Some Delicious Deep-Dish Pizza

A trip to Chicago would not be complete without a hearty slice of deep-dish pizza. It's truly a must-do and one of the nicest things to do in Chicago after a long day of sightseeing. With so many restaurants to try, it might be difficult to find the perfect one for you. Try Lou Malnati's Pizzeria located on Wells Street, which is famous for its characteristic crusts. Or perhaps Pequod's Pizza, located on North Clybourn Avenue, where food and drinks are available until late. 

crime bus tour
Hop on the Mob and Crime Bus Tour

Even though their crimes are long forgotten, people are still fascinated with Chicago's prohibition-era mobsters. Names like Al Capone, Dion Johnny Torrio and Bugs Moran, are still well-known and often referenced in movies and TV shows. The city has transformed so dramatically in the last century that it's difficult to understand that seemingly benign areas were the site of a terrible war in the 1920s and 1930s. Embark on a 90-minute Mob & Crime Bus Tour. This tour delves into Chicago's dark past, profiling notable figures and prominent sites like the location of the Valentine's Day Massacre as well as the Biograph Theatre, where John Dillinger was assassinated by FBI officers.

Field Museum
Visit One of the Largest Natural History Museums in the World

The Field Museum's collection has grown to more than 24 million objects since it opened in 1893, making it one of the best and largest natural history museums in the world. With large Neoclassical halls housing fossils, rare gemstones, and animal and plant species, this is a place to fuel your passion for the natural world. There's also compelling anthropology for the Ancient Americas and Egypt, as well as Tibet, China, Africa, and Pacific Islands cultures. You can't miss the main attraction, a 37-meter-tall Titanosaur in the Stanley Field Hall.

museum or exhibition showcase
Discover the Amazing History of the City

In Lincoln Park, you may learn about Chicago's rich history by visiting various thematic exhibitions. Facing Freedom delves into the different conflicts for freedom that afflicted Chicago from the 1850s through the 1970s, including the Civil War, women's suffrage, labor union development, and Japanese incarceration. At Crossroads of America, you can enter a jazz club or ride Chicago's very first L train, while the Chicago dioramas depict the city's rapid expansion from a lonely frontier outpost to an enormous metropolis.

Visit the Holy Name Cathedral

Chicago's Gothic Revival Catholic cathedral, located near the Chicago Station, was completed in 1875 after its predecessor was destroyed in the Great Chicago Fire of 1871. Visitors with keen eyes will see an overarching Tree of Life Theme in the building's fittings. Upon arrival, you'll be met by the cathedral's massive bronze doors, each weighing more than 500 kg and cast to seem like planks of wood. Inside, the Stations of the Cross crafted from in Rocco Alicante marble, the sculptures of the Evangelists made from bronze, and the bishop’s throne for the Chicago Diocese are all worth a closer look. 

North Avenue Beach
Have a Stroll on North Avenue Beach

Despite being significantly isolated from the city's fabric, Lincoln Park contains what many consider to be the nicest beach in the city. North Avenue Beach stretches for a few hundred meters up to Diversey Harbor, with piers at regular intervals to prevent the sand from washing away. On the beachfront, there's a bar and companies that rent and teach kayaking and stand-up paddle boarding. International contests are held at the South Volleyball Courts, while the Chicago Air & Water Show is held in August at North Avenue Beach.

red roof bedding
Book Your Stay at Red Roof

What are you waiting for? Book your stay near the heart of Chicago with Red Roof!