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Things To Do In Chicago - A House Sitter's Guide

By Liam Beauchamp-Jones | House sitting


Despite being known as ‘The Windy City’, Chicago isn’t a place purely to be enjoyed when wrapped up warm or inside. Whilst we certainly wouldn’t blame you for staying in (after all, if you’re pet sitting in Chicago, why would you want to prise yourself away from your cute, new surrogate pet?), there’s also many amazing places to explore in this city with your new four-legged friend in tow.

With this in mind, we’ve put together a guide of things to do in Chicago. Some of these suggestions are for you to enjoy alone in the marvellous Mecca of the Midwest, while others permit Dennis the dog to come along too!

Art Institute Of Chicago

With the greatest Impressionist collection outside Paris, the Art Institute of Chicago is a must if you’re looking for things to do in Chicago. A permanent collection of more than 3,000 artworks, including many classic masterpieces, are on display for your wonderment. If contemporary art is more your area of appreciation, make sure you head to the spectacular Modern Wing. You can also travel the globe via the art of ancient Greece, Japan, Africa and the Americas. Visit the Art Institute of Chicago when Mittens is happily dozing at home and you have some hours to kill!  

Navy Pier

Navy Pier sits on the shoreline of Lake Michigan and encompasses fifty acres of parks, gardens, shops, restaurants, family attractions and exhibition facilities. It’s one of the most visited attractions in the entire Midwest and dogs are welcome at most of the outdoor areas of this local landmark. If you’re looking after a dog while house sitting in Chicago, why not head here on a sunny day and take your new friend for a stroll? If you get peckish, they can accompany you to the outside seating area at the food court. Following this, you could hop on one of the Architecture Boat Tours to get some incredible views of the city. They depart from the Ogden Slip at Navy Pier and accept pooch passengers too. 

Wrigley Field

Located on the North side of Chicago, Wrigley Field is a baseball park which is home to two Major League Baseball (MLB) franchises. Come here to holler for the Chicago Cubs from the stands. To make it an even more authentic baseball experience, ensure this is done with an ice-cold drink and a hot dog in hand! If you arrive early, you’ll be able to watch training and avoid the mad rush to get in. Better yet, if you want your new furry BFF to join you, this may well be possible. Dog friendly games are often held at the ballpark. In fact, they’ve had quite a run, enjoying dog friendly games for 20 seasons! Previous events such as the ‘Bark in the Park’ have gone down a treat with dog owners.


However, if baseball isn’t your bag, there are plenty of other things to do at Wrigley Field including special events throughout the year. 

Chicago Bean

Unfortunately, dogs aren’t permitted into Millennium Park, which is where you will find the infamous Chicago bean. However, there’s no rule that prevents you from taking them for walks around the perimeter. From afar, you can still see the impressive and unusual attraction. Plus, you could always return at a later date when pooch is all tired out and happy to snooze in his bed! After all, you wouldn’t want to miss out on the ultimate opportunity for a selfie at this local landmark!


Have you ever used TrustedHousesitters for house sitting in Chicago? What do you make of our above guide? Did you discover any other fun things to do in Chicago? We would love to hear your thoughts and stories. Please comment below or contact us on social media. Alternatively, why not tag us in a photo of your time in the city with your surrogate pet? Find us on Instagram with the hashtag #TrustedTales.

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