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House Sitters America

House sitting & pet sitting exclusively for the US

House sitting in Chicago

Chicago regularly ranks in the top 5 for pet-friendly cities in the US. It is renowned for leafy parks and outdoor activities.

So... there's a whole lot of pet owners in Chicago, and when these loving pet owners go on holiday, they need the very best care for their pets—and the best care option is getting a pet sitter.

Getting a pet sitter is easy on House Sitters America. You can choose to pay for the sitter, or get a sitter for free (many will sit for you in return for free accommodation). Either way, your fur-babies get to stay in their own home, with in-home care—the one place on earth where they feel safest.

House sitting and Pet Sitting in Chicago, Illinois - a fantastic, alternative to dog boarding.

100% free for pet owners in Chicago

Pet owners in Chicago never pay anything to register, place an ad, search for and contact pet sitters or book one in to look after their pets and home.

After more than a decade serving our membership, our website is secure and safe, with features that make the whole experience really easy.

Backed by our award-winning customer support team, we have helped to facilitate hundreds of thousands of successful sits—providing comfort and security to millions of pets and peace of mind for their owners.

100% awesome for pet sitters in Chicago

This site is free to explore and easy to use. We provide a secure space for sitters to find house sitting jobs in Chicago or anywhere across the US.

Sitters can choose to sit locally in Chicago or they can choose to travel—or both. They can choose to either charge for their services, or sit for free in return for free accommodation.

Either way, sitters can save, or earn tens of thousands of dollars by offering a service that brings enormous joy to some adorable pets—and great confidence for the house owners.  

House sitting and Pet Sitting in Chicago - the perfect in-home alternative to dog boarding in Chicago

Chicago: That Pet-Lovin’, Toddlin’ Town

Chicago has dozens of indoor doggy play areas and doggie daycares throughout the city so that furry friends can get exercise and social time even when the temperatures drop.

Caring for cats, on the other hand, is no problem: they are happy to trade a warm fire for the snow all winter long.

House Sitting and Pet Sitting in Chicago

Looking for big-city sophistication with a heavy dose of Midwestern “aww, shucks” niceness? Then Chicago is the place for you.

While the weather can be unpredictable—it’s named “The Windy City” for a reason, after all—the historic architecture, an expansive lake that looks remarkably like an ocean, bountiful museums, lively theater scene and, hello, the FOOD (can we all give a big cheer to deep dish pizza?) more than make up for a rain- or snow-lashed day.

House Sitting and Pet Sitting in the City

Lincoln Park

This is the neighborhood movies are made of. Stately brick row houses engulfed by colorful trees with falling leaves. There is also the Lincoln Park Zoo, which is always free to the public, and restaurants and bars galore on Lincoln Avenue.

Lake View

Love the Cubs? (And who doesn’t these days, right?) Welcome to Lake View, home of the iconic Wrigley Stadium. There are restaurants and theaters, historic row houses, amazing restaurants, a lively nightlife and so much more. All within walking distance—no car required. (Easy access to The El and other public transportation too!)

Logan Square

This is one of the hottest places to be in the city right now. If you’re lucky, there will be a speakeasy in the basement of the apartment where you are house sitting, or a great bowl of foodie-class ramen will be right around the corner.

West Loop

It’s all about the food here. Plain and simple. Eat, work, eat, drink, repeat.
Wicker Park/Bucktown
This is a young, vibrant neighborhood full of urban professionals who can still go out during the week, and rally for that big early-morning meeting the next day.

River North

Walk from a high-rise apartment along the river to grab a drink or a doughnut, relax on a rooftop deck—there’s no reason to ever leave this happenin’ neighborhood. It’s all right here.

Hyde Park

This has the most inviting green space in all of Chicago—perfect for walking furry friends in your care. Enjoy a picnic, lay out on the beach or play a game of Frisbee. This is also home to the revered University of Chicago.

Lincoln Square

This is where young married couples go to start a family when they aren’t quite ready to turn their backs on the city and head to the suburbs. There are brownstones, tree-lined streets and locally owned restaurants, but the city is just a stone’s throw away. 

House sitting and Pet Sitting in Chicago, the home of deep dish joy

House Sitting and Pet Sitting in the Suburbs

The North Shore

If you’ve ever watched Ferris Bueller’s Day off or The Breakfast Club, you’ve seen the North Shore. The affluent suburbs bordering Lake Michigan here include Wilmette, Kenilworth, Winnetka, Glencoe and Lake Forest, to name a few. The homes are gracious and often historic, though older bungalows are steadily being torn down for a new McMansion. If you’re there during the summer, be sure to catch an outdoor concert at Ravinia or take a walk along with your furry companions on the Green Bay Trail.

The Western Suburbs

As Chicago has grown and become increasingly expensive, mush of the residential and business growth has moved west. Suburbs like Naperville, Aurora, Wheaton and Buffalo Grove still have a small town charm with more of a big-city vibe. You’ll find friendly neighborhoods with beautiful, single-family homes, wide sidewalks for dog walking and great places to eat without having to trek into the city.

The South Side

We’ve gotta be honest. There is a side of Chicago that has a not-so-great reputation when it comes to violence. And some of the most crime-ridden locales are on the south side. Don’t get us wrong: there are still some very attractive suburbs here, like Oak Lawn and Crestwood. But take caution in areas like Markham, Harvey and Riverdale, which have a reputation for gang-related violence.

East Suburbs, aka Indiana

Cities like Crown Point, Munster, Hebron, Cedar Lake…these are just a few cities in Indiana offering easy access to downtown Chicago in an hour or less. (Traffic permitting.) The towns are small and inviting, and more affordable than the “real” Chicago ‘burbs. Who knew, right?

House sitting and Pet Sitting in Chicago - the perfect in-home alternative to dog boarding in Chicago

House sitting & pet sitting in Chicago

From the food to the theater, from the lake to the museums, Chicago is a truly great American city that is not to be missed. Once you start to explore this gem of a destination, you’ll only want more and more.

Just remember to keep walking: those hot dogs and deep dish pizza are not exactly calorie-free.