Things to do in Chicago

What to expect in Chicago

The things to do catalogue in Chicago is led by Observation decks, Attraction passes, Museums, Cruises and Tours, so you’ll find everything from quick city viewpoints to multi-attraction bundles and museum visits. That spread means travellers can combine a single iconic ticket with a pass or a relaxed cruise to cover different budgets and trip styles. Demand peaks in May and is quietest in February, so experiences are busiest in May and much easier to book in February.

How to choose what to book

A key choice is whether you want a single attraction ticket or a multi-attraction pass, and that decision shapes budget and flexibility: the widest range is in Attraction passes, where the typical price is AUD 170 and the usual upper end reaches AUD 211. For straightforward, predictable spending the Tours category has a narrow spread and a typical price of AUD 42, so shopping around gains little.

If you need the most affordable way in to activities, consider Tours with a typical price of AUD 42 for filling itinerary gaps. Museums and Observation decks sit between budget and premium, with Museums typically around AUD 49 and Observation decks typically around AUD 46, so they suit travellers wanting reliable value without the commitment of a full pass.

When travellers from Australia book

Most travellers book very close to travel, typically about 1 day ahead, while the earliest planners often book around 8 days ahead, so plan on short lead times rather than months of advance planning. That small cushion matters most in May, when demand is at its highest.

How prices compare across top categories

The table below shows how the city’s top categories stack up on typical price and the usual range so you can set a budget before choosing.

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.