Things to Do in Chicago
Ten stops running from a stainless steel bean that reflects the whole skyline back at you to a pizza style thick enough to eat with a fork and knife.
Chicago runs on architecture, deep-dish, and a lakefront that shapes the whole city's layout, this list heads past what the quiz already covers toward a reflective sculpture that's become the city's unofficial symbol, an architecture cruise through the city's building history, and a pizza rivalry that locals take considerably more seriously than the jokes suggest. Ten stops below, plus a quiz elsewhere on this site if you fancy testing what stuck.
Cloud Gate & Millennium Park
Officially titled Cloud Gate but universally known as The Bean, this 110-ton stainless steel sculpture reflects the surrounding skyline and visitors in a seamless, mirror-polished surface, taking artist Anish Kapoor's team years to achieve a finish without a single visible weld line. The wider Millennium Park runs free outdoor concerts through summer at the Jay Pritzker Pavilion, alongside the Crown Fountain, two glass towers that project changing faces and periodically spout water directly onto delighted kids below.
This gets busy at almost any hour given how central and photogenic the sculpture is, an early morning visit helps specifically if you want photos without other visitors in the reflection.
Hours Daily, roughly 6am-11pm
Address 201 E Randolph St, Chicago, IL
The Art Institute of Chicago
One of the oldest and largest art museums in the country, holding one of the most significant Impressionist collections outside France, alongside American Gothic, one of the most parodied paintings in history, and Georges Seurat's massive pointillist masterpiece A Sunday on La Grande Jatte. The two bronze lion statues flanking the museum's main entrance have become iconic Chicago landmarks in their own right, regularly dressed in sports jerseys when local teams reach the playoffs.
This is far too large to cover in a single visit, pick a few specific galleries rather than attempting the whole collection given how much ground the museum actually spans.
Hours Daily, roughly 11am-5pm, hours vary
Address 111 S Michigan Ave, Chicago, IL
Chicago Deep-Dish Pizza
Deep-dish pizza, baked in a deep, buttery crust with the cheese layered beneath the sauce rather than on top, was invented in Chicago in 1943, considerably different from the thin, foldable style found in most other cities. Lou Malnati's and Giordano's both run real, long-standing rivalries over which restaurant makes the definitive version, most locals hold a real preference for one over the other.
Expect a proper wait, deep-dish pizzas take considerably longer to bake than a thin crust, order as soon as you sit down given the 30 to 45 minute cook time most restaurants require.
Address Lou Malnati's, multiple locations, Chicago, IL
Willis Tower Skydeck
Once the tallest building in the world for nearly 25 years, Willis Tower's Skydeck runs at 1,353 feet, and The Ledge, a series of glass boxes extending directly out from the building's edge, lets visitors stand over the street with nothing but transparent glass beneath them. On a clear day, views stretch across four states, Illinois, Indiana, Michigan, and Wisconsin all visible from the same observation deck.
Book timed tickets ahead during peak season, this is one of the most visited attractions in the city and queues without a reservation can run considerably long.
Hours Daily, roughly 9am-10pm, hours vary seasonally
Address 233 S Wacker Dr, Chicago, IL
Museum of Science and Industry
The largest science museum in the Western Hemisphere, exhibits covering everything from a full-scale coal mine tour to a real submarine captured during World War Two, U-505, one of the few German U-boats preserved intact anywhere in the world. A live baby chick hatchery runs year-round, chicks hatching in real time in front of visitors, a memorable, hands-on detail beyond the larger exhibits.
This is considerably larger than most visitors expect, allow a full day given how many distinct wings the museum actually covers.
Hours Daily, roughly 9.30am-4pm, hours vary
Address 5700 S DuSable Lake Shore Dr, Chicago, IL
Chicago Architecture River Cruise
Chicago's status as the birthplace of the modern skyscraper makes this river cruise an essential way to understand the city, knowledgeable docents narrate the history and design of dozens of buildings along the Chicago River, several of which pioneered techniques still used in skyscraper construction worldwide. This is considerably more informative than a standard sightseeing boat tour, a good one specifically if architecture interests you even slightly.
Book ahead during peak summer season, the most popular time slots sell out days in advance given how consistently well-reviewed this specific tour runs.
Best time Late afternoon for the best light on the skyline
Address Chicago Riverwalk, Chicago, IL
Navy Pier
A lakefront pier running since 1916, home to a 196-foot Ferris wheel offering sweeping views over Lake Michigan and the skyline, alongside an IMAX theatre, a stained glass museum, and regular fireworks displays through the summer season. This works well as a family day, the mix of rides, restaurants, and lake views holds attention across a wide range of ages.
This gets busy on summer weekends and evenings, an earlier visit helps if you'd rather avoid the heaviest crowds along the pier itself.
Hours Daily, roughly 10am-10pm, hours vary seasonally
Address 600 E Grand Ave, Chicago, IL
Lincoln Park Zoo
One of the few free zoos remaining in a major American city, running continuously since 1868, home to gorillas, big cats, and a well-regarded farm-in-the-zoo section specifically designed for younger kids to interact directly with animals. The zoo sits within the wider Lincoln Park itself, a proper green space along the lakefront that rewards exploring beyond just the zoo grounds.
This works particularly well for a full family day given the free entry, a good combination with a walk through the wider park and its adjacent conservatory.
Hours Daily, roughly 10am-5pm, hours vary seasonally
Address 2001 N Clark St, Chicago, IL
Wrigley Field
Home to the Chicago Cubs since 1916, Wrigley Field remains the second-oldest ballpark in Major League Baseball, its ivy-covered outfield walls, planted in 1937, remain one of the most distinctive features in the sport. Rooftop seating on buildings directly across the street from the park has run since long before the stadium itself allowed such views officially, an unmatched Chicago tradition found nowhere else in the sport.
Tours run outside game days, covering the park's full history and giving access to areas not normally open during an actual game, book one if attending a live game doesn't fit your schedule.
Address 1060 W Addison St, Chicago, IL
Chicago's Blues Clubs
Chicago holds one of the most significant blues traditions in the country, electric blues developed here directly following the Great Migration, when musicians brought Delta blues north and amplified it for the city's louder club scene, a sound that later influenced rock and roll considerably. Kingston Mines and Buddy Guy's Legends, both still running regular live shows, remain among the most established, well-regarded clubs for hearing the genre performed live.
This makes for a good evening activity, check the current lineup ahead given how much the specific performers shift night to night.
Address Buddy Guy's Legends, 700 S Wabash Ave, Chicago, IL
Best time to visit Chicago
May through September covers the most comfortable window for the majority of this list, mild enough for the outdoor and lakefront stops without winter's real cold and wind. For the full month-by-month breakdown, see our Best Time to Visit Chicago guide.
Late afternoon and early evening specifically suit the architecture river cruise and the skyline views from Willis Tower, time those two around golden hour if photography matters to you.
Getting around Chicago
The L train covers this list well, Chicago has one of the more extensive public transit systems in the country, a car generally works against you here given traffic and limited downtown parking. If you're mapping out exactly how to spend your time, our 24 Hours in Chicago and 2 Day Chicago Itinerary guides lay out an hour-by-hour and day-by-day plan.
Keeping an eye on costs? Chicago on a Budget covers what's free and where the tourist markup actually is. Travelling as a couple? Chicago for Couples covers Willis Tower at sunset and a river cruise. And once your dates are set, Where to Stay & Eat in Chicago breaks down the neighbourhoods.
Frequently asked questions
- Is Chicago worth visiting beyond deep-dish pizza?
- Yes, easily, the Art Institute, the architecture river cruise, and Wrigley Field all offer a considerably deeper experience than the food alone suggests.
- How many days do you need in Chicago?
- Four days gives a comfortable pace to cover downtown's main sights, one major museum, and a Cubs or Sox game if the schedule lines up.
- Is Chicago expensive to visit?
- Moderate, several major attractions on this list run free or reasonably priced, though accommodation downtown runs pricier than the wider national average.
- What's the best Chicago trip for kids?
- The Museum of Science and Industry and Lincoln Park Zoo both rank as the most reliably kid-friendly stops on this list.
That's ten decent slices of a city properly shaped by its own architecture and lakefront.
A note before you plan around this: prices, opening hours, booking requirements and admission details in this guide were correct at the time of writing, but venues change these often and sometimes without notice. Always check directly with the attraction or its official website before you travel or build a schedule around a specific time or price.
Before travelling to any destination featured on this site, please also check your government's latest travel advice, as safety situations, entry requirements and travel warnings can change.
