Discover house sitting in Chicago

Stay in wonderful places by house sitting and caring for cute pets.

Discover house sitting in Chicago

Stay in wonderful places by house sitting and caring for cute pets.

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Why you'll love pet and house sitting in Chicago, IL

An illustration of a cat laying on his pet bedForget hotel rooms

From home comforts to the calming company of pets, house sitting offers so much more.

An illustration of a glowing green heartIt feels good to give

Explore new places while making a difference to the lives of pets and people along the way.

An illustration of a house with a tree in the foregroundA new perspective

You don’t have to travel far. With pet and house sitting, you can find a world of adventures just around the corner.

An illustration of three coins with paws in them

A win-win without money

When you’re house and pet sitting, you provide free house and pet care. And pet parents offer you free accommodation in return for looking after their home and furry friends. The only cost is your annual membership, making it an affordable and fulfilling way to travel.

Find out more about memberships

I am so blessed to have this experience and to be able to have a companion by my side the entire time. I’m forever grateful for the opportunity TrustedHousesitters provides! This is truly life changing.

Adelia, sitter member from Bath, UK

Popular pet sitting and house sitting destinations

Feel safe, secure and supported

An illustration of a speech balloon with five stars on itRead feedback from sitters

Want to know if a house sit is right for you? Look for feedback previous sitters have left on the pet parent's listing.

An illustration of stacked documentsHome & Contents Plan

House sit in homes with peace of mind they’re covered at no extra cost to you or the pet parent.

An illustration of a dog sniffing the air24/7 Vet Advice Line

With a free direct line to a dedicated team of veterinary nurses, you can quickly clear up any pet queries.

Ready to start your Chicago house sitting adventure?

Join our worldwide community and start your membership today.

Discover pet and house sits across the United States

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Chicago house sitting FAQs

With an annual sitter membership, animal lovers like you can enjoy free accommodation all over the world in exchange for pet care. Live like a local with a cute pet pal by your side as you provide peace of mind to pet parents who know their adorable animals are in the best of hands. Apply for as many sits as you like and get ready for meaningful connections and unforgettable adventures, all made possible by pets!

Choose your membership plan and create a profile that stands out from the pack - include clear photos, relevant experience, and references (these don’t have to be from previous house sitting jobs). Next, set up a saved search to be the first to find out when house sitting jobs in Chicago become available for your chosen dates. Once you’ve found the ideal sit, write a personalized message to the pet parents explaining why you are the perfect person for the job! Find out more with 10 tips on how to become a house sitter.

Your number one priority when house sitting in Chicago will be taking care of the pets. Daily walks, mealtimes, and lots of cuddles will be top of the agenda as most house sits include a pet. Aside from this, house sitters in Chicago need to keep the home clean and tidy and send regular updates to the pet parents about their precious pet pals.

At TrustedHousesitters, our members are driven by a genuine love of pets, not getting paid. They exchange passionate pet care for free accommodation, gaining a wealth of experiences and memories to last a lifetime.

House sitting in Chicago

Are you ready for the Windy City? With its elegant skyscrapers, gorgeous lake, and chic boutiques, Chicago has long been a popular destination. What's the best way to see it? By house sitting, of course! Try house sitting in Chicago to experience the Windy City just like a native.

When you sign up for house sitting in Chicago, you'll be able to enjoy the trip of a lifetime. You'll be caring for cute animals as well as seeing the sights. Take your new canine companion for a walk along the banks of Lake Michigan, use kitty cuddles to escape the chill of the Windy City, and enjoy some amazing adventures along the way!

Looking after a dog in Chicago: the best of the Midwest

As soon as you set foot in Chicago, you'll easily see why it's inspired so many famous movies and TV shows! This stunning city is best explored on foot, and what better way to do it than with a pup by your side? If you are looking after a dog in Chicago, you will want to head straight for the Riverwalk or the Lakefront Trail for the best views in town. You'll be amazed at the sheer size of the mighty Lake Michigan, and you'll be able to enjoy that famous skyline as you take Fido for a walk!

A house sitting summer in the Windy City

Your Chicago experience will be wildly different depending on the time of year you visit. This Midwest city has some extreme temperatures, so be prepared! If you're looking after a dog in Chicago in summer, then be ready for it to get hot, hot, hot. Don't worry, though, as this city may be inland but it still has beaches! There are over two dozen free sandy beaches on the shores of Lake Michigan, and some are dog friendly. It's the perfect solution for a hot summer's day.

Looking after a dog or cat in Chicago in winter

When the mercury drops, Chicago gets seriously cold! If you're house sitting in Chicago in winter, be sure to bring your thickest coat and scarf. This is a great time to curl up in your temporary home, snuggling with your new dog or cat pals on the couch. The good news? By day, you can have fun indoors by visiting great museums like the world-famous Art Institute and at night... Well, the best way to keep warm is with a hearty helping of deep dish Chicago pizza!

A house sitting job in Chicago offers you a unique, magical way to experience this thriving city in the heart of the Midwest. Sign up to TrustedHousesitters' pet-loving community now, and get ready for a trip you'll never forget!