Things to Do in Chicago
Prices, opening hours, best times to visit and the stuff nobody tells you, everything you need for a first trip to Chicago, Illinois, plus one pigeon's opinions on all of it.
Right, Chicago. Windy City, deep dish pizza, skyscrapers that basically invented the skyscraper, a city that turned a real catastrophe into the foundation of modern architecture. This is the proper, no-nonsense guide to things to do in Chicago: what things actually cost, when to go, what to skip, and which bits are worth the queue. Six main stops below, plus a quiz elsewhere on this site to see if you were paying attention.
Chicago's Architecture & River Cruise
Chicago is often credited as the birthplace of the modern skyscraper, following its rapid postfire rebuilding, steel-frame construction pioneered here after the Great Chicago Fire changed how cities were built worldwide, freed from the need for thick load-bearing masonry walls, buildings could suddenly go up rather than just out. A Chicago Architecture Center river cruise, boats gliding along the Chicago River past skyscrapers designed by some of the most significant architects in American history, is the best way to understand this legacy.
It's a proper 90-minute tour with knowledgeable guides pointing out specific buildings and the innovations they introduced, worth booking ahead given how popular it is, particularly in summer.
Best time Late afternoon, for good light on the buildings
Getting there Boats depart from several docks near Michigan Avenue
Deep Dish Pizza
Chicago is famous for a deep, thick-crust style of pizza, distinct from thinner regional versions, a fierce, decades-long rivalry exists with New York over whose version is better, and Chicago residents defend deep dish with real conviction. Lou Malnati's and Giordano's are the two most famous names, both worth trying, expect a real wait at peak times and a considerably longer cooking time than a standard pizza given the depth and layering involved.
It's a proper meal rather than a quick slice, order well ahead of when you're actually hungry, deep dish takes a full 30-45 minutes to bake all the way through.
Best time Order ahead if possible, given the cooking time
Lake Michigan & the Lakefront Trail
Chicago sits on the shore of Lake Michigan, the lake defines much of the city's waterfront and skyline views, genuinely more like an inland sea than a lake, the far shore isn't visible from the city. The Lakefront Trail, running for miles along the water, is free and one of the best ways to see the skyline from a different angle, walking, cycling, or just sitting at one of the many beaches along the route.
Navy Pier, further along the waterfront, adds a livelier, more commercial stretch with rides, restaurants, and boat tours, worth combining with a lakefront walk if you want both quiet and activity in the same outing.
Best time Any time; sunrise for skyline photos from the water
The Art Institute of Chicago
A world-class art museum, home to one of the finest Impressionist and Post-Impressionist collections outside Europe, including Georges Seurat's A Sunday on La Grande Jatte and Grant Wood's American Gothic, both significant works worth seeking out specifically. The famous bronze lion statues flanking the entrance have become an iconic Chicago photo spot in their own right.
It's a sizeable museum, plan at least half a day to see the highlights properly rather than rushing through.
Hours Daily, roughly 11am–5pm, Thu until 8pm
Address 111 South Michigan Avenue, Chicago
Cloud Gate ('The Bean')
A massive, mirror-polished steel sculpture in Millennium Park, officially called Cloud Gate but universally known as 'The Bean' for its shape, reflecting the surrounding skyline and passersby in a mesmerising, constantly shifting way. It's free, one of the most photographed pieces of public art in the country, and worth the visit even if you've seen a hundred photos already, it's considerably more impressive in person.
Millennium Park itself, the wider space around the Bean, rewards a proper wander, including the Crown Fountain's changing video projections and, in summer, free outdoor concerts at the Pritzker Pavilion.
Address Millennium Park, central Chicago
Willis Tower Skydeck
One of the tallest buildings in the Western Hemisphere, the Skydeck on the 103rd floor includes glass viewing boxes, 'The Ledge', that extend out from the building, letting you look straight down over a thousand feet, not for anyone with a fear of heights.
It gets busy, particularly in summer, timed tickets booked ahead help avoid the worst of the queue, and clear days offer views stretching across four states.
Hours Daily, roughly 9am–10pm
Address 233 South Wacker Drive, Chicago
Best time to visit Chicago
April through June and September through October give the most comfortable weather for the amount of walking this list involves, mild without summer's occasional heat or winter's famously biting cold. For the full month-by-month breakdown, see our Best Time to Visit Chicago guide.
Chicago winters are seriously intense, the 'Windy City' nickname is felt considerably more sharply off the lake in January than in July, worth packing accordingly if travelling in the colder months, though museums and deep dish restaurants work just as well regardless of season.
Getting around Chicago
Chicago's 'L' elevated train system covers the city well and is properly useful for reaching neighbourhoods beyond downtown. Central Chicago, including Millennium Park and the Art Institute, is walkable, and the Lakefront Trail is best covered on foot or by bike rental. 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?
- Yes, easily, the architecture and river cruise alone justify the trip, and the Art Institute, Millennium Park, and deep dish pizza scene all add real depth beyond the skyline.
- How many days do you need in Chicago?
- Three days covers the architecture cruise, the Art Institute, and the lakefront comfortably without rushing.
- Is Chicago expensive?
- Moderate, generally cheaper than New York or San Francisco for accommodation and dining, though the Willis Tower Skydeck and river cruise are worthwhile paid attractions.
- What is Chicago famous for?
- Being the birthplace of the modern skyscraper following the Great Chicago Fire, deep dish pizza, and its position on Lake Michigan.
That's everything I've got.
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.
