Chicago
When are you traveling?
Time of Day
Duration
Price
$0
$500+
Rating
Specials
All Chicago Tours

Chicago makes such a striking impression that you're best off discovering it from a few different vantage points. Luckily, Chicago tours offer multiple ways to see the city in style. Visit the observation decks in the Windy City's record-breaking skyscrapers for panoramic views; then, hop on a boat along the Chicago River. From there, zoom into a more local scale: Head out after dark to learn about the city's gangster history; explore its characterful neighborhoods on local-led walking tours—and don't forget to eat Chicago classics, from deep-dish pizza to Italian beef sandwiches, on a tasting tour.

445 results

en
3a23ab62-ce08-421a-b065-53c3e0d5135d
things_to_do
People Also Ask
Q:How much do Chicago tours cost?
A:

The cost of Chicago tours runs the gamut from roughly US$20–30 per person for a 45-minute architecture cruise to US$850 and up (depending on group size) for a private tour of the city. Most of the top-rated tours are under US$60 per person. No matter what you have on your agenda, there’s sure to be a tour that suits your budget.

Q:What do you see on Chicago tours?
A:

There are dozens of subjects you can explore and sights you can see on Chicago tours, so what you see depends on which tour you choose. The city’s famous skyline gets the spotlight on architecture boat tours, and several walking tours highlight locations tied to Chicago’s history of organized crime. You can also see Chicago landmarks like the Cloud Gate sculpture (“The Bean”) in Millennium Park and the much-loved Field Museum of Natural History.

Q:How many days in Chicago is enough?
A:

You could spend weeks and not run out of things to do in Chicago, but a 3–5-day visit is a great way to start. That gives you time to see the city’s highlights, and you might even have enough time to book some longer Chicago tours, like an extended river cruise or even a boat tour on the lake.

Q:What is the best month to visit Chicago?
A:

The best months to be in Chicago are spring shoulder seasons (specifically April–May) and fall (September–October). During these months, the weather isn’t as hot and humid as it can get in the summer, but it’s still pleasant enough for plenty of outdoor exploring. The summer calendar is packed with fun festivals and events, so summer can also be a great time to visit if you don’t mind the heat (or the crowds).

Q:What is the #1 attraction in Chicago?
A:

According to travelers, some of the top attractions in Chicago are the Chicago Riverwalk, The Magnificent Mile, the Willis Tower Skydeck, the Chicago River, and the Navy Pier. Other popular attractions are Millennium Park, the Wrigley Building, the Chicago Theatre, and the Shedd Aquarium. And many of these are located within relatively easy walking distance from one another.