10 Best Things to Do in Chicago

Looking for what to do in Chicago? Set along the shores of Lake Michigan, Chicago is a city of bold architecture, world-class museums, deep-dish pizza, jazz and neighbourhoods packed with character. It combines a dramatic skyline and rich history with friendly Midwestern energy, making it one of the most rewarding big cities to explore in the United States.

From walking the lakefront and cruising the river to discovering vibrant districts, iconic viewpoints and legendary food, Chicago offers something for every type of traveller. Here are the 10 best things to do in Chicago to help you plan the perfect trip.

1. Explore Millennium Park and “The Bean”

Millennium Park is one of Chicago’s most recognisable spaces and the natural starting point for many visits. The star attraction is Cloud Gate, the gleaming stainless-steel sculpture affectionately known as “The Bean,” which reflects the skyline, sky and surrounding plaza in surreal curves.

After taking the obligatory photos, wander the rest of the park to find the Jay Pritzker Pavilion, Crown Fountain and landscaped gardens. In summer, free concerts and events bring the park to life, while in winter the nearby ice rink adds a classic cold-weather touch.

2. Stroll the Magnificent Mile

The Magnificent Mile, a stretch of Michigan Avenue running north from the Chicago River, is the city’s most famous shopping and strolling corridor. Lined with flagship stores, historic buildings, hotels and restaurants, it offers a mix of luxury boutiques, familiar brands and architectural icons.

As you walk, look up to admire landmarks such as the Tribune Tower and Wrigley Building, then detour down side streets for quieter cafés and views towards the river and lake. At night, the area glows with lights and feels particularly atmospheric.

3. Take an architecture cruise on the Chicago River

Chicago is often described as an open-air museum of architecture, and the best way to appreciate it is from the water. Architecture cruises along the Chicago River glide between skyscrapers while guides explain how the city rebuilt after the Great Fire and pioneered new design styles.

You’ll pass famous buildings by architects such as Mies van der Rohe, Jeanne Gang and Louis Sullivan, learning how each era left its mark on the skyline. Evening cruises add the bonus of sunset colours and illuminated towers reflected in the river.

4. Visit the Art Institute of Chicago

One of the top art museums in the world, the Art Institute of Chicago houses an extraordinary collection spanning thousands of years and nearly every corner of the globe. Highlights include Impressionist masterpieces by Monet, Renoir and Degas, iconic works like Grant Wood’s “American Gothic” and a renowned collection of modern art.

Beyond famous canvases, you’ll find photography, design, ancient artefacts, Asian art and rotating exhibitions that reward slow exploration. The museum’s location beside Millennium Park makes it easy to combine both in one day.

5. Enjoy views from a skyscraper observation deck

Chicago’s skyline is best appreciated from above. Two main observation decks compete for attention: the Skydeck at Willis (formerly Sears) Tower and 360 CHICAGO at the John Hancock Center. Both offer sweeping views over the city grid, Lake Michigan and, on clear days, several states on the horizon.

The Skydeck features glass boxes extending out from the building, allowing brave visitors to stand directly over the city streets below. At 360 CHICAGO, the TILT attraction leans you outward over the glass windows for an extra thrill. Choose one deck — or both — depending on how much vertigo you can handle.

6. Walk or cycle the Lakefront Trail

Chicago’s Lakefront Trail runs for miles along the shore of Lake Michigan, linking beaches, parks, museums and neighbourhoods. This car-free path is popular with runners, cyclists, dog walkers and families enjoying the breezes and open views.

Rent a bike or simply walk a section between Grant Park, Museum Campus and the North Avenue Beach area. In warm months, people sunbathe on the sand, sailboats dot the water and the city’s skyscrapers form a dramatic backdrop to the lake.

7. Explore Chicago’s neighbourhoods

Beyond downtown, Chicago is a city of neighbourhoods, each with its own identity. In the West Loop, converted warehouses now house trendy restaurants, cafés and galleries. Wicker Park and Bucktown mix indie shops, street art and nightlife, while Pilsen showcases colourful murals and Mexican-American culture.

Further north, Lincoln Park offers leafy streets, a free zoo and historic homes, while Andersonville and Uptown reveal layers of immigrant history, live music venues and cosy bars. Exploring a few different areas gives you a deeper sense of how Chicagoans actually live.

8. Visit Museum Campus: Field Museum, Shedd Aquarium and Adler Planetarium

On a peninsula jutting into Lake Michigan, Museum Campus gathers three of Chicago’s major attractions in one scenic area. The Field Museum showcases natural history, including dinosaur skeletons, ancient cultures and detailed exhibits on ecosystems around the world.

Next door, Shedd Aquarium houses marine life from the Great Lakes to coral reefs, while the Adler Planetarium offers immersive shows about space and astronomy. Even if you don’t go inside every museum, the campus’ waterfront walkways provide some of the best skyline views in the city.

9. Experience Chicago’s music and theatre scenes

Chicago has deep roots in jazz, blues and gospel, and live music remains a key part of its culture. Legendary clubs and intimate venues across the city host performances most nights of the week, from classic electric blues to contemporary jazz and indie bands.

The city is also a powerhouse for theatre and comedy. Consider catching an improv show at a famous comedy institution, a play in the Theatre District or a smaller production in neighbourhood venues. These nights out reveal a creative side of Chicago that many visitors miss.

10. Eat like a local: pizza, hot dogs and beyond

No visit to Chicago is complete without sampling its signature dishes. Deep-dish pizza, with its buttery crust, thick layers of cheese and chunky tomato sauce, is the most iconic — though locals also love tavern-style thin crust cut into squares. Chicago-style hot dogs, loaded with mustard, relish, onions, tomatoes, pickles, sport peppers and celery salt (but never ketchup), are another must-try.

Beyond the classics, you’ll find an exciting food scene spanning steakhouses, global cuisines, neighbourhood bakeries, coffee shops and creative tasting menus. Exploring Chicago’s dining options is one of the most enjoyable ways to understand the city’s diversity and character.