The 22 Best Things to do in Chicago

Chicago is one of the biggest cities in the United States. It is a great destination as it appeals to all kinds of travellers whether you are a couple, have the kids in tow, are with a group or going solo. It has plenty to do all year round with lots of activities for making the most of the good weather as well as places to visit on rainy days. Planning a trip and looking for some destination inspiration for The Windy City? Here are some of the best things to do in Chicago.

22 Cool Things to do in Chicago

1. Meander around Millennium Park

‘The Loop’ area of Chicago is where you’ll find Millennium Park, one of the city’s most visited attractions. This vast green space plays host to lots of events throughout the year, many of which are free. In the summer, it’s a great place to lay about and enjoy a picnic and outdoor film screenings. To make the most of Millennium Park, take a guided tour and discover all the cool aspects of this great space.

2. Admire the Cloud Gate sculpture

You probably know the Cloud Gate sculpture as ‘The Bean‘. This Chi-Town iconic landmark is in Millennium Park. Admiring The Bean is one of the top things to do in downtown Chicago. This public piece of art is one of the world’s largest permanent outdoor art installations. Its reflective surface is inspired by liquid mercury and reflects the sky and clouds. As the name suggests, it is a gate to bridge the gap between the sky and the viewer.

3. Relax along the Riverwalk

The Riverwalk boardwalk stretches 1.25 miles. It is located on the south bank of the Chicago River, right in the heart of downtown. It is a great free thing to do in the city and a perfect spot for a family-fun day. As you stroll you’ll stumble upon cute cafes and casual bars. There are lots of areas and benches where you can sit and stare at the soaring skyline. The pedestrian trail is also decorated with lots of public art.

4. Take in the views from the Willis Tower

If your neck is sore from looking up, head to The Skydeck Chicago at Willis Tower so you can look down over the city. This is the third tallest building in the Western Hemisphere and is home to ‘the Ledge’. This is a small glass box some 1,353 feet in the air that extends out from the Skydeck. If you can bear to look down and out, the views are sweeping and span across four states.

5. Brave Chicago’s highest thrill ride

If you want your panoramic views to include the Willis Tower, then head up to the 360 Chicago Observation Deck. From the 94th floor of the former John Hancock Center, you’ll have breathtaking views of the city skyline and Lake Michigan from 1,000 feet above the Magnificient Mile. Here you can experience Tilt, Chicago’s highest thrill ride which lets you lean out over the skyline some 1,030 feet below. The ride gives you downward-facing views as well as heart palpitations. Thankfully, when it’s all over you can grab a much-needed drink at Bar 94, Chicago’s highest bar with 360-degree views.

6. Ride the Ferris Wheel at Navy Pier

The Centennial Wheel is the city’s iconic Ferris Wheel. You’ll find it at Navy Pier on the shores of Lake Michigan. As you can imagine, the views from the top of the Ferris Wheel are magnificent. Apart from Centennial Wheel, Navy Pier has lots of fun things to do for all the family. For instance, you can enjoy free concerts and events, play at the amusements and shop till you drop.

7. Hike or bike the 606

The 606 is a former elevated railroad track transformed into a recreational trail and green space. Running along the Bloomingdale Trail, the 606 stretches some 2.7 miles between Ashland Avenue and Ridgeway Street. Full of art installations and landscape design there is plenty to look at as you walk or cycle through four different Chicago neighbourhoods. It is a great way to explore the area and best of all, it’s free.

8. Visit famous filming locations in Chicago

Chicago is a star on the big screen as so many movies have been filmed here. A great way to get to know the city is through some of its most recognisable filming locations. For instance, at 671 Lincoln Avenue in Winnetka you’ll find the McAllister house from Home Alone. The former IBM building at 330 N. Wabash Avenue is Wayne Enterprises in the film The Dark Knight. The Skydeck of Willis Tower features in both Ferris Bueller’s Day Off and The Dark Knight. If you are a fan of the film High Fidelity, head to the Kinzie Street Bridge and the Green Mill Cocktail Lounge.

things to do in chicago

9. Drink like a mobster at the Green Mill Cocktail Lounge

Speaking of the Green Mill Cocktail Lounge, this former speakeasy and, reputedly Chicago’s oldest surviving drinking establishment, is a great place to drink like a gangster. Chicago is synonymous with prohibition-era speakeasies, as well as the gangsters associated with them. Rumour has it Al Capone and his fellow mobsters frequented The Green Mill Cocktail Lounge. The building’s underground tunnels were used to traffic booze. Nowadays, the joint is a cool jazz bar.

10. Listen to the blues at Kingston Mines

If blues is more your style, there is no finer place to enjoy the music than Kingston Mines. This world-famous blues nightclub in the Lincoln Park area of Chicago is legendary and steeped in history. Founded in 1968, Kingston Mines is the largest and oldest continuously operating blues club in Chicago. Scores of musical greats have played the stages here. With its warm welcome and relaxed vibe, this club lives up to its motto: “Hear Blues – Drink Booze – Talk Loud – You’re Among Friends!”.

things to do in chicago

11. Marvel at masterpieces at the Art Institute of Chicago

For a culture fix, head to the Art Institute of Chicago which is home to one of the best impressionist collections in the country with 300,000 permanent pieces. It is also home to the largest group of Monet’s stacks of wheat in the world. Due to the sheer size of this museum, you should plan at least a few hours to wander around admiring the impressive artworks. Apart from Monet, you’ll find masterpieces on the walls by Degas, Renoir, Cézanne, Magritte, Pollock, Warhol, Dali, Kandinsky and Picasso.

things to do in chicago

12. Learn more at the Chicago History Museum

Another magnificent museum is the Chicago History Museum, which brings the story of Chicago to life in imaginative ways. Through the absorbing and engaging exhibits, you’ll learn all about Chicago blues music, Chicago-style hotdogs and Chicago’s place in the civil war. It covers everything and there is something enjoyable here for everyone making it fun for all the family.

things to do in chicago

13. Shop till you drop at the Magnificent Mile

Looking for the best place to bash your credit card? Head to the Magnificent Mile to browse the more than 460 stores. This 13-block stretch of North Michigan Avenue is a great place to indulge your passion for shopping no matter how deep your pockets. Whether you are after electronics or cosmetics, stuff for your home or your pet, designer labels or brilliant bargains, you’ll find it all here in this shopping district.

things to do in chicago

14. Devour deep dish pizza at Lou Malnati’s

Lou Malnati started making deep dish pizza in the 1940s when he began working in Chicago’s first deep dish pizzeria. He opened the first Lou Malnati’s Pizzeria in 1971 in Lincolnwood. When Lou died his sons took over the business with their mother. This is a truly authentic family-run Chicago business and it just happens to serve some of the best deep dish pizza in the city.

15. Eat a Chicago-style hotdog at The Wieners Circle

A Chicago dog is a hotdog made with an all-beef frankfurter which is placed in a sesame seed roll. It is then topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. Due to all the toppings, the hotdog is said to be “dragged through the garden”. Oh, and don’t dare ask for ketchup. Chicagoans shun this condiment on their dogs. There are plenty of vendors around the city, but one of the best places to chow down is at The Wieners Circle. However, the hotdogs here come with a side of insults, all friendly of course, but you have been warned.

16. Enjoy a gourmet food tour

Whilst there are great food joints all over the city, having a local take you to the best ones is a great way to discover where and how Chicagoans eat. For sure on a tour, you’ll enjoy some of the city’s most iconic foodstuffs including deep-dish pizza, hot dogs and an Italian beef sandwich. But you’ll also taste decadent desserts, artisan chocolates and classic Chicago-style popcorn, which is caramel and cheddar flavours mixed together. Click here for 7 of the best Chicago food and drink tours.

things to do in chicago

17. Catch a game at Wrigley Field

Wrigley Field opened in 1914. This makes it the second-oldest active baseball park in the major leagues. Located on the North Side of Chicago, it’s the home of the Chicago Cubs, one of two major league baseball (MBL) teams in the city. The other team is the White Sox. Wrigley Field (named after the chewing gum manufacture) is famed for its unique traditions and charm. These include the ivy-lined outfield walls and historic man-operated scoreboard. Catching a game here is a memorable experience whether you are a baseball fan or not.

18. Watch the White Sox play

The White Sox play at Guaranteed Rate Field on Chicago’s south side. This field isn’t as historic or charming as Wrigley Field, but nonetheless, games here great because the White Sox are white-hot. They are a proper old-school slugging team making games exciting for spectators. They are also teeming with talented players who are fun to watch.

things to do in chicago

19. See one of the coolest car parks in the world

Local architect Bertrand Goldberg designed Marina City, one of Chicago’s landmark buildings. The two cylindrical towers have 19 floors of continuously spiralling parking spaces. The thought of which is enough to make you dizzy. At one stage, it was the world’s tallest residential building and tallest concrete structure. Nowadays, it is one of the most famous and coolest car parks in the world thanks to an appearance in the Steve McQueen movie The Hunter. 

20. View the city from the water

Did you know that the Chicago River is the only river in the world that permanently flows backwards? In 1887, the Illinois General Assembly reversed the flow of the river through civil engineering. To learn more about this fascinating body of water, and to see the city from a different perspective, get out on a boat. There are loads of boat companies offering all types of boat tours. Some focus on the city’s history, some on the architecture and some are more general sightseeing tours. Just head down to the Riverwalk and see which boat tours and companies are best suited to you.

21. Paddle Lake Michigan

Lake Michigan is one of the five Great Lakes of North America. It is a water lover’s delight as there are just so many things to do on the water and on the shoreline. For instance, you can enjoy the buzzing beaches, the beachfront bars and clubs and lots of recreational activities too. A fun thing to do is to paddle around in a canoe, kayak or on a stand-up paddleboard. As you navigate the sometimes choppy waters, you’ll glide past Navy Pier and have sweeping views of the skyscraping skyline. If you don’t have your own equipment or want to join a group, you’ll find operators at Monroe Harbor and North Avenue Beach.

things to do in chicago

22. Explore Lincoln Park

Lincoln Park is a beautiful area on the North Side of Chicago. It’s a great place to visit as there are things to do for all ages. There are lots of lovely restaurants and bistros and art galleries as well as lots of things to do outdoors. The park is full of landscaped gardens and water features and the lakefront is a great spot for a picnic or to just sit and soak up the views. The indoor botanical garden is a blooming marvellous place, especially when it rains. Lincoln Park is also home to the Lincoln Park Zoo, which is one of the oldest zoos in the United States.

things to do in chicago

Melanie May

Melanie is an intrepid solo traveller, endlessly curious about people, places and food. She is a fan of slow travel and loves exploring the world by mouth, discovering a culture through its food. Having backpacked her way around the world she turned her wanderlust into a career and is now a full-time travel writer.

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