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The Peninsula Chicago, Chicago

Things to do guide

The best things to do in Chicago

Updated 1 October 2026 · 16 things to do

Pictured: The Peninsula Chicago

Chicago is the great American city that doesn't shout about it. It simply has the skyscrapers (it invented them), the lake (so big it has beaches and waves), the deep-dish pizza, the blues clubs, and a downtown that's happy to let you walk everywhere. It's brash, friendly and surprisingly beautiful.

Give it four days if you can. Spend one on the Loop and Millennium Park, one on a river architecture cruise and the lakefront, one in a world-class museum, and the rest eating and wandering neighbourhoods. Come in summer for the lake, or any other season for fewer queues.

Don't miss

  1. 1Millennium Park
  2. 2The Art Institute of Chicago
  3. 3A Chicago architecture river cruise
  4. 4Skydeck Chicago
  5. 5Deep-dish pizza

The big sights

Downtown packs a lot into very few blocks.

  1. Millennium Park

    Landmark

    The Chicago skyline reflected under Cloud Gate in Millennium Park
    Photo: Roman Boed from The Netherlands, CC BY 2.0

    The city's front garden is home to Cloud Gate, the giant mirrored bean that bends the skyline and the faces of everyone who walks beneath it. Nearby are Crown Fountain, where faces on glass towers spout water, and the Frank Gehry-designed Pritzker Pavilion, with free concerts in summer.

    Photograph the Bean early in the morning, before the crowds arrive.

  2. The Art Institute of Chicago

    Museum

    A bronze lion guarding the front of the Art Institute of Chicago
    Photo: Marlin Keesler from Streamwood, IL, CC BY 2.0

    One of the great art museums of the world, guarded by two bronze lions on Michigan Avenue. Highlights include Seurat's A Sunday on La Grande Jatte, Hopper's Nighthawks and Grant Wood's American Gothic. The Impressionist galleries alone justify the trip.

    Tip: Pick a few galleries and enjoy them properly rather than trying to see everything.

  3. A Chicago architecture river cruise

    Activity

    The Wrigley Building and DuSable Bridge on the Chicago River
    Photo: Matt Kieffer from London, United Kingdom, CC BY-SA 2.0

    Chicago gave the world the skyscraper, and the best way to see why is from a boat on the Chicago River. Guides explain the great towers that line the water, from the Wrigley Building to Marina City, and the story of the fire that cleared the way for them.

    Go on a clear day, and take a jacket. It's cooler on the water than you expect.

    Tip: Book a tour run by the Chicago Architecture Center for the best commentary.

  4. Skydeck Chicago

    Landmark

    The glass Ledge on the Skydeck at Willis Tower
    Photo: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0

    On the 103rd floor of Willis Tower, once the tallest building in the world, glass-floored boxes called the Ledge stick out from the building so you can look straight down at the street. On a clear day you can see across Lake Michigan to other states.

    Tip: Visibility is everything here, so go on a clear day and arrive early.

  5. The Magnificent Mile

    Neighbourhood

    Michigan Avenue's Magnificent Mile lined with shops and towers
    Photo: Ken Lund from Reno, Nevada, USA, CC BY-SA 2.0

    The stretch of Michigan Avenue north of the river is Chicago's shopping boulevard, lined with big-name stores, hotels and a handsome Gothic water tower that survived the 1871 fire. It's a good place to people-watch.

The lakefront

  1. The Chicago Riverwalk

    Activity

    Kayaks and tour boats along the Chicago Riverwalk
    Photo: Jules Verne Times Two, CC BY-SA 4.0

    A promenade along the south bank of the river, with cafés, kayak rentals and bars tucked under the bridges. It's a lovely place to wander on a summer evening, with the skyline reflected in the water.

  2. Lakefront Trail

    Activity

    An 18-mile path hugging Lake Michigan, perfect for cycling or walking, with beaches, harbours and city views along the way. Hire a bike and go for a ride north from Navy Pier to Lincoln Park.

    On a hot day, stop at North Avenue Beach for a swim and a view of the skyline.

  3. Museum Campus

    Museum

    The columned Field Museum of Natural History
    Photo: Joe Ravi, CC BY-SA 3.0

    A lakeside park that holds three major museums: the Field Museum, home of the Tyrannosaurus rex called Sue, the Shedd Aquarium and the Adler Planetarium. The skyline view from the Adler's terrace is one of the best in town.

Neighbourhoods and baseball

  1. Wrigley Field

    Landmark

    Wrigley Field, home of the Chicago Cubs
    Photo: Sea Cow, CC BY-SA 4.0

    One of the oldest ballparks in the major leagues, with ivy on the outfield walls and the old scoreboard still turned by hand. Even if you don't follow baseball, a Cubs game in the summer sun is a great way to feel like a local.

    Tip: Book game tickets ahead, as popular fixtures sell out.

  2. Pilsen

    Neighbourhood

    A Mexican-American neighbourhood south-west of the Loop, covered in murals and full of bakeries, taquerias and small galleries. Walk along 18th Street, and stop at the National Museum of Mexican Art.

  3. Wicker Park

    Neighbourhood

    A creative, hip district of indie shops, vintage stores, coffee bars and some of the best bars in the city. Walk along Milwaukee Avenue and see which doorway looks good.

  4. Oak Park

    Day trip

    The front of Frank Lloyd Wright's Home and Studio in Oak Park
    Photo: John Delano, CC BY-SA 4.0

    A leafy suburb a short train ride west, where Frank Lloyd Wright lived and worked for two decades. His Home and Studio is open for tours, and the streets around are lined with other Wright houses, among the finest examples of his Prairie style.

Eat, drink and listen

  1. Deep-dish pizza

    Food

    A Chicago-style deep-dish pizza from Pizzeria Uno
    Photo: Bobak Ha'Eri, CC BY 3.0

    A thick, buttery crust piled high with cheese, toppings and chunky tomato sauce, baked in a pan and eaten with a knife and fork. Lou Malnati's, Giordano's and Pequod's are among the places locals argue about. It takes about 45 minutes to bake, so order a salad and settle in.

    Tip: Order your pizza as soon as you sit down, because it takes a while to cook.

  2. A Chicago-style hot dog

    Food

    A Chicago-style hot dog loaded with toppings
    Photo: Capvideo, CC BY-SA 4.0

    An all-beef frank on a poppy-seed bun, piled with mustard, onions, bright green relish, tomato, a dill spear, sport peppers and celery salt. One rule: never ask for ketchup. Italian beef, a sandwich of thin sliced beef dipped in gravy, is the other classic.

  3. The blues clubs

    Nightlife

    Chicago blues is electric, loud and unmistakable, having been shaped here by musicians from the Mississippi Delta. Clubs such as Buddy Guy's Legends in the South Loop and Kingston Mines on the north side keep it alive nightly.

Where to stay in Chicago

Not sure which area suits you? Read our guide: Where to stay in Chicago →

Getting around

You don't need a car downtown. The L trains and buses reach most sights and neighbourhoods, and the Loop and the Magnificent Mile are walkable. Ride-hail fills the gaps, and trains link O'Hare and Midway airports to the centre.

When to go

Summer is the most fun, with lake beaches, festivals and outdoor concerts, though it can be hot and humid. Late spring and early autumn are comfortable, and winters are cold and windy, with fewer crowds and cheaper rooms.

Questions about visiting Chicago

What is Chicago best known for?
Its architecture and skyscrapers, Millennium Park and Cloud Gate, the Art Institute, deep-dish pizza, blues music and its Lake Michigan shoreline.
How many days do you need in Chicago?
Three or four days covers the main sights, a museum, an architecture cruise, the lakefront and some great meals.
What is there to do in Chicago with kids?
Kids enjoy the Field Museum's dinosaurs, Navy Pier, the Bean at Millennium Park and the Museum Campus, and a summer afternoon on the lakefront beaches.
Do you need a car in Chicago?
No. The L trains, buses and your own two feet cover the main sights, and parking downtown is expensive and tricky.

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