Hide COVID19 Information - Stay safe and well   READ MORE

How It Works


Since subscribing to your site, I have had a steady summer house/pet sitting job with a local family. It has provided me with experience, references and new friends. Thank you Sherry

More Sitter testimonials (50)

Thanks, I managed to contact a lovely lady who is planning to mind my 8 year old labrador for 10 weeks while I visit unwell family. Just fantastic! Jon G

More Owner testimonials (50)

House & Pet Sitting in Chicago

House and Pet Sitting in Chicago, Illinois - a fantastic, free alternative to dog boarding. The picture is Cloud Gate, Millenium Park

Chicago: That Pet-Lovin’, Toddlin’ Town

Did You Know? Extreme weather does scare some Chicagoans away from owning dogs, but not everyone. Fortunately, there are 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 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?

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. 

*FREE: House sitting is usually free, for both sitter and house owner, although this is completely up to the individuals. There are usually some costs that need to be covered by either the sitter or the house owner e.g. electricity, phone usage, vet fees etc. How these costs are handled needs to be agreed before the sit begins. House sitters pay a single annual membership fee, while house owners pay nothing to advertise their house or to contact sitters.