Whether it’s your first visit or a repeat trip, this list of things to do in Chicago covers the essentials along with a few ideas for getting off the beaten path.
1. Visit Willis Tower Skydeck
No list of things to do in Chicago is complete without Willis Tower Skydeck — it’s the single most recommended stop for visitors and a reasonable place to start your trip.
Top-Rated Chicago Tours & Experiences
2. Explore Art Institute of Chicago
Art Institute of Chicago is the next stop most travelers add to their Chicago itinerary, and it pairs naturally with a full day of sightseeing.
3. Spend an evening exploring the nightlife or evening atmosphere
Many destinations feel different after dark. Spending at least one evening exploring bars, night markets, or evening cultural performances in Chicago can round out a trip that’s otherwise mostly daytime sightseeing.
4. Wander the old town
Set aside time to simply walk through the older parts of Chicago without a fixed plan — this is often where the character of the destination comes through most clearly, in the architecture, the small shops, and the everyday rhythm of local life.
5. Take a food tour or sample local specialties
Food is one of the most direct ways into a place, and Chicago is no exception. A guided food tour is an efficient way to try several local specialties in one outing, or you can simply seek out a well-reviewed local spot on your own.
6. Catch the view from a rooftop or viewpoint
Most destinations have at least one spot that rewards the climb — in Chicago, look for a rooftop bar, observation deck, or natural viewpoint for a wider perspective on the city or landscape.
7. Visit a local market
A local market in Chicago is a good way to see everyday commerce up close, pick up souvenirs that aren’t mass-produced, and get a sense of what residents actually buy and eat.
8. Join a guided walking tour
A guided walking tour is one of the most efficient ways to cover a lot of ground in Chicago while picking up context and history you’d likely miss exploring solo.
9. Explore a museum or cultural site
Chicago has no shortage of museums and cultural sites worth an afternoon, particularly for travelers who like their sightseeing paired with a bit of history.
10. Take a boat trip or cruise, if available
If Chicago has a waterfront, harbor, or river running through it, a boat trip is often one of the more relaxing ways to see the destination from a different angle.
Frequently Asked Questions
What is Chicago best known for?
Chicago is best known for Willis Tower Skydeck, which draws the majority of first-time visitors and remains the top attraction in the area.
How many days do you need to see the best of Chicago?
Around 3 days is generally enough to cover the top things to do in Chicago, though a longer stay allows time for day trips and slower exploration.
Is Chicago good for a family trip?
Yes — most of the things to do in Chicago listed here, including guided tours and walking routes, work well for a range of ages, though it’s worth checking specific activity requirements in advance.
What should first-time visitors prioritize in Chicago?
Willis Tower Skydeck and Art Institute of Chicago are the two most commonly recommended stops for first-time visitors to Chicago, and both are worth building the rest of your day around.
Related: How Much Do Tours in Chicago Cost? Chicago Tour Prices (2026)
Plan Your Tours in Chicago
Ready to book? See our full roundup of the best tours and experiences in Chicago for guided options, skip-the-line tickets, and day trips.
Write Your Review
No reviews yet. Be the first to share your experience!