Top picks for Chicago City passes

Discover 148 City passes in Chicago on Trip.com, updated 31 October 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From SGD 10.44 per person, with an average total of SGD 85.80. Choose the option that suits your plan.

With 12.568k verified reviews, City passes Chicago boast an average rating of 4.8.

This week's most popular City passes: "Chicago Architecture River Cruise", with 4.695k reviews and a 4.9 rating.

Now on Trip.com: "Chicago: Fulton Market Guided Donut Tour", a 2-hour adventure in Chicago!

The next available day tour departs on 1 November 2026. Book now to secure your spot!

Chicago City passes usually take about 2 hours — perfect for a relaxed, immersive experience!

45% of Chicago City passes now offer English-speaking guides

October is the perfect time to visit Chicago! Choose from 148 available day tours, including seasonal favorites like Chicago Architecture River Cruise.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

Search attractions or local attractions & tours
Book now for today
Book now for tomorrow

148 results for Chicago City passes

1
2
3
4
5
6
8

Frequently asked questions about Chicago City passes

How many City passes are available in Chicago on Trip.com?

What are the best City passes in Chicago?

What are the top-rated City passes in Chicago?

How can I contact Trip.com customer support?

Can I change or cancel my booking?

How can I get discounted prices?

Reviews/Trip Moments

★
★
★
★
★
Reviews:
Guest User2026-01-20
We had a great time touring Chicago with our guide, Nick. He was personable and knowledgeable, and kept the conversation interesting for the whole family (mom + 3 kids ages 12, 10 and 7). It was legit FREEZING the morning of our tour with windchill -20 or so, but Nick knew plenty of places to take a break and warm up before venturing back into the cold. The donuts were amazing - each of the four of us had a different favorite - and the variety was impressive. My main advice is to eat 1/4 of each donut at the most - you will run out of room!! Thanks again to Underground for a fun experience with the kids.