Things to do in Chicago

Discover top things to do in Chicago 

 What are the best things to do in Chicago? 

We can’t wait to show you some of the best things to do in Chicago – they range from luxurious day trips to hair-raising action adventures and vibrant cultural events, with plenty of culinary highlights thrown in to keep you wanting more. Some of the most popular activities that Chicago tourism has to offer include: 

• 360 CHICAGO Observation Deck
• Flyover in Chicago
• Chicago CityPASS®: Experience 5 must-see attractions
• Architecture River Tour
• Chicago: Willis Tower Skydeck and The Ledge Ticket

Search Wotif to discover what’s on in Chicago in 2025 and start getting excited about everything you’ll get to see while you’re in town – from festivals, events, natural wonders, concerts and gigs. There’s a wide selection of Chicago day tours – experience the area’s gorgeous surroundings with the help of a local guide or set off on your own adventure like the explorer you are.  

How can I find the cheapest things to do in Chicago on Wotif? 

We’ve got insider information on what to do in Chicago that will go easy on your wallet, with prices starting from AU$8. To find more, use the dropdown “Sort by” menu and choose price as your criteria. Or for even better results, choose “Price + our picks” to figure out what to see in Chicago in 2025 at some of the best prices out there. Refine your search by using filters and Bob’s your uncle – trip planned, budget (and mischief) managed. Keep an eye out for discounts and promotions. Before you book, check for coupons or promotion codes on any of the listings.  

Why should I book activities in Chicago with Wotif? 

You’ll get access to 206 Chicago things to do in our large inventory – excellent chances of finding exactly what floats your boat. Keep an eye out for specials, discounts and promotions. Locking in your things to do is easy as pie: use our smooth and intuitive booking system and call on our friendly 24/7 customer service if you need a hand. To be extra discerning, read our guest ratings to find activities in Chicago that match your expectations.  

What is the cancellation policy on booking activities in Chicago with Wotif?  

We make it transparent and easy to see whether you can cancel your activity booking in Chicago. The words “Fully refundable” in green next to the image on the activity listing give you the freedom to change your mind later. Even if the activity you’ve planned isn't fully refundable, it’s often easy enough to change the dates without incurring any additional fees – just make sure to carefully check this before you book.