Pet Setting & Drop Ins in Loop, Chicago
Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

Graduate Student Who Loves Dogs
West Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking
"My 110lb Doberman Poodle mix ADORES Madalyn! He is so happy to see her. Highly suggest introducing your furry child to their soon to be favorite human! Mada... (more)"

A happy dog, makes a happy world!
West Town, Chicago, IL, 60642
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care
"Corbin is a trustworthy and caring human that your pup will love! I'm so lucky to have him in my and my pup's life. He is my go-to whenever I need anyone to ... (more)"

Graduate Student and Dog Lover!
Near North Side, Chicago, IL, 60610
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Holly was fantastic with my pup Minnie and provided great summaries about her check-ins. Minnie is pretty stubborn pup, so I really appreciate Holly's patien... (more)"

The Dawg Whisperer!
Near North Side, Chicago, IL, 60611
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
"Kelyn is an amazing dog-sitter. He's caring, responsible, and always very attentive to pets. He thoroughly enjoyed playing with my dog and made sure he got h... (more)"

Responsible dog handler
Near South Side, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
"She has watched all 3 of my dogs at once! I completely trust her with them! I know that they are a hassle but she makes taking care of them look easy! She cr... (more)"

You'll get ALL the puppy pics! :)
West Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"This was my first time using Rover and Ashley exceeded all my expectations. I have 2 very social cats so just leaving food and water doesn’t quite cut it. As... (more)"


Love to walk, watch and run dogs!
Near North Side, Chicago, IL, 60610
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
"Maddi has grown up with dogs all her life. she has experience with all size breeds and is a huge dog lover! Maddi understands what they need and can adapt ... (more)"
Rover also offers pet setting & drop ins in these other Chicago neighborhoods:
Avondale | Beverly | Brighton Park | Mount Greenwood | Norwood Park |
Riverdale | Rogers Park | South Shore | West Garfield Park | West Pullman |
Rover.com is the simple, savvy way to find and book Loop, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Loop, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.
A Daily Treat: A Blog by Rover
Rover's got you covered, even when you don't need a dog sitter. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:
- Top 100 Dog Names and Unique Dog Names, depending on your preference
- Dog Doors: Everything You Need to Know to Find the Right Fit
- 5 Common Dog Fears and How to Help
Book a Stay, Donate to a Cause
Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Loop, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.
We're proud to support over 200 organizations across the nation, including: