Things to do in Chicago

What to expect in Chicago

This catalogue is led by Observation decks, Attraction passes, Museums, Cruises and Tours, giving a mix of skyline views, packaged attraction access and cultural visits that suits first-time sightseers and repeat visitors alike. Attraction passes and Observation decks sit at the top by booking volume, so you’ll find both quick-entry experiences and longer guided options. Demand peaks in June and is at its quietest in January, so June visits tend to be busiest while January bookings are much easier to secure for the same experiences.

How to choose which activities to book

The main choice is whether you prioritise skyline views, packaged access or museum time — decide if you want the landmark view or a multi-attraction pass. Attraction passes offer the widest range: entry-level at PHP 5,946 and upper-end around PHP 8,385, so they suit travellers who want flexibility; Observation decks are consistently focused around PHP 1,843, so shopping around gains less. For filling schedule gaps the most affordable way in is Tours, typically around PHP 1,665, while Museums and Cruises sit in the mid-range where what’s included varies more between options.

When travellers from the Philippines usually book

Most travellers book very close to travel, typically 1 day ahead, while the earliest planners book about 8 days ahead. Plan on booking one to four weeks ahead only if you prefer extra cushion for peak season: that matters most in June.

How Chicago activities compare by price

The table below shows how the city’s top activity categories compare on price so you can place a budget before you pick an experience.

Typical price is the median paid on Klook; the usual range covers the middle half of bookings, so cheaper and pricier options exist outside it; prices are shown with their currency code. Based on Klook booking data, August 2025 – July 2026.