Pet Sitting & Walking Services in Chicago, IL

At Masters' Guild, we provide professional pet sitting and walking services to ensure your pets receive the care, attention, and exercise they need. Whether you’re away for a short trip or require regular walks for your dog, our experienced pet sitters and walkers are here to help. With us, your furry friends are in safe and loving hands.

What pet sitting and walking costs in Chicago, IL (2026)

Estimates: typical US ranges adjusted for Chicago's regional price level (about 4% above the national average; BEA Regional Price Parities 2024, all items, Chicago-Naperville-Elgin MSA (103.595/100)). Get two or three quotes for your exact job.

Our Pet Sitting & Walking Expertise in Chicago, IL

Why Choose Masters' Guild for Pet Care?

• Trusted Professionals: Our carefully vetted sitters and walkers are experienced in pet care, ensuring your pets are safe and happy.
• Tailored Services: We customize our services to meet the unique needs of your pets.
• Convenient Booking: Easily schedule pet care services through our user-friendly app.
• Reliable & Caring: We treat your pets like our own, offering the love and attention they deserve.

Get Started Today!

Post your Pet Care Quest through our app and connect with trusted sitters and walkers. Whether it’s pet sitting or dog walking, Masters' Guild ensures your furry friends are well cared for while you’re away.

Pet Sitting & Walking Services We Offer

Masters' Guild provides a variety of pet care solutions tailored to your needs:

• Pet Sitting: Personalized care for your pets in the comfort of their own home.
• Dog Walking: Regular walks to keep your dog active, healthy, and happy.
• Playtime & Exercise: Engaging activities to ensure your pets stay entertained.
• Flexible Scheduling: Book services as needed, from one-time visits to daily care.
• Mobile-Friendly Platform: Easily book, track, and manage your pet care services through our app.

What's different about pet sitting and walking in Chicago

Chicago's winters bring average January lows near 16.5°F and lake-effect snow bursts that can bury a sidewalk within the hour, so a dog walk planned for midday can turn into a slow, icy trip by evening. Summers swing the other way, with July highs averaging 84.1°F, which pushes most owners toward shorter, shaded midday visits instead of long walks. The city's housing stock adds its own wrinkle: much of Chicago is built up in masonry two-flats and three-flats and brick bungalows dating mostly to the 1900s-1940s, many with raised basements, so a sitter or walker needs clear instructions for shared entries, buzzers, and stairs before they can even reach your pet.

Because pet sitting and dog walking are largely unlicensed trades here, the vetting falls to you: ask about liability insurance or bonding and pet first-aid certification, and hold overnight in-home stays to a higher bar, with a background check, references, and a plan for key handling, since a sitter watching your home in Lincoln Park or Wicker Park is trusted with more than the pet. Demand for full-week vacation coverage peaks every July and August alongside summer travel, so sitters serving dense neighborhoods like Logan Square and Lakeview book up fast; lining up care three to four weeks ahead keeps your options open.

What moves the price in Chicago

• Chicago winters (January lows averaging 16.5°F, lake-effect snow bursts) mean shorter, more careful walks and sitters comfortable on icy sidewalks
• Many homes are older two-flats, three-flats, and bungalows with raised basements, so sitters need clear access and stair instructions
• Pet sitting is unlicensed in Illinois, so insurance, bonding, and pet first-aid certification matter more than credentials
• July and August are peak vacation season, so book overnight or vacation-week coverage three to four weeks ahead

Licensing and permits in Illinois

Pet sitting and dog walking are largely unlicensed trades in the US and Canada; look for sitters who carry liability insurance/bonding and pet first-aid certification, and treat overnight in-home care as requiring a higher trust bar (background check, references, key handling) than a licensed trade would.

Residential building permits in Illinois are issued locally — by the city, village, or (in unincorporated areas) the county building/zoning department — not by a state agency, so requirements and fees vary by municipality. In Chicago, permits come from the City of Chicago Department of Buildings.

Tax: Pure labor is generally NOT taxable in Illinois when no tangible personal property changes hands and labor is billed separately from materials; but if a contractor sells parts/materials as part of the job, Service Occupation Tax can apply to the materials (and the labor if it's bundled into one selling price rather than itemized separately).

Best time to book in Chicago

July and August are peak vacation season and holiday weekends also surge; book 3-4 weeks ahead in busy cities for summer or major holidays. Peak demand: July and August. Typical job length: 30 min per visit; overnight jobs run nightly; a vacation-coverage job typically spans 5-7 days.

DIY or pro? A trusted neighbor or friend can informally cover feeding/walks for short trips, but hire an insured, background-checked professional for overnight stays, medication administration, or trips longer than a few days.

Areas we cover in Chicago

Pros on Masters' Guild take pet sitting and walking jobs across Chicago neighborhoods including Lincoln Park, Wicker Park, Logan Square, Lakeview, Hyde Park, Pilsen, Bronzeville and West Loop.

Frequently Asked Questions

Sources: Our Pet Sitting and Walking cost guide. Updated 2026-09-06.

We Also Serve These Nearby Satellite Cities

In addition to Chicago, IL, we also offer Pet Sitting and Walking in nearby areas, including the following satellite cities:

• Evanston, IL

• Oak Park, IL

• Cicero, IL

• Skokie, IL

• Schaumburg, IL

• Des Plaines, IL

• Naperville, IL