Pet Sitting & Drop Ins in Grand Boulevard, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Labor Day
Elizabeth S.
Looking to bond with your furry palHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

About: I have lived with dogs and cats my entire life and have walked, fed, and played with animals on a daily basis since I was a child! I'm great with eve… (more)

from
$17
per visit
Calendar Recently Updated
Sarai O.
2.
Reliable, trustworthy & loving!Bridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Sarai was the best!!! So thoughtful and careful with my baby girl and so transparent through out the entire weekend. I’ll definitely be hiring her again! If you… (more)

from
$35
per visit
Calendar Recently Updated
Walter L.
3.
Loving your dogs like my own :)Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

I never have to worry about my dog Juniper when she is with Walter. I love Juniper deeply and want only the best care for her and thats what Walter provides. Ha… (more)

from
$17
per visit
Confirmed availability: Labor Day
Adrianne N.
Summer Break Teacher looking 2 HelpHyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking

Nicole creates a safe, loving and enjoyable environment for all animals she works with. Her passion for life and the joy animals bring her helps her create qual… (more)

from
$17
per visit
Confirmed availability: Labor Day
Marissa W.
Loving MamabearBridgeport, Chicago, IL, 60616
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

My name is Judith and Marissa would be a perfect employee for Rover. She is knowledgeable, responsible, loving and patient with my (2) Shih-Tzu's that she walks… (more)

from
$20
per visit
Calendar Recently Updated
Responsible, dependable, pet loverHyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I have seen sabrina be very attentive and caring towards my cat cleo and my past cat Garfield. She tends to them frequently and makes sure they’re grooming is u… (more)

from
$18
per visit
7.
Caring and experienced dog loverKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

So responsive and followed all instructions perfectly . Was so kind and trusted her with my dog (more)

from
$20
per visit
Calendar Recently Updated
8.
Reliable routine Queen for your petBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Erin was so great and easy to work with! She followed my cat’s instructions/routine perfectly and sent updates with pictures during each visit. She even went ab… (more)

from
$15
per visit
Calendar Recently Updated
Care for pets as if they were mine!Bridgeport, Chicago, IL, 60608
Drop-In Visits, Dog Walking

Esmeralda is amazing with dogs. She is careful with their feeding habits and they never stop having fun. I regularly have her take care of my three small doggo'… (more)

from
$20
per visit
Calendar Recently Updated
All-size animal loverHyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking

Isabella cares deeply for any and all animals!! She has experience watching dogs and cats and has an amazing dog of her own. She is very reliable and will also … (more)

from
$12
per visit
Confirmed availability: Labor Day
11.
Caring for favorite family member😊Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Barbara is a fun loving and energetic pet care taker. She grew up with pets and therefore is patient and very comfortable around all pets! I have trusted Barbar… (more)

from
$17
per visit
Calendar Recently Updated
12.
Owner/foster of shy+reactive dogsHyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking
12 years of experience

About: I started volunteering to walk dogs at an animal shelter in 2011. In 2013, I began fostering. I have fostered dogs (particularly shy or reactive), ca… (more)

from
$25
per visit
Calendar Recently Updated
Love Has Four Paws!Englewood, Chicago, IL, 60621
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I have watched Alexsandra with her Pets and how they grew up. She is super calm, and very patient and she loves animal with all of her heart. I have a pet of my… (more)

from
$17
per visit
Confirmed availability: Labor Day
14.
Active lifestyle-fenced yard!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

10/10 recommend! Mike is absolutely wonderful with all dogs that he comes in contact with. His background and experience with dogs in a military setting makes h… (more)

from
$30
per visit
15.
E 
Verified Background Check
Rover 101
Animal Loving FamilyGrand Boulevard, Chicago, IL, 60653
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

She was great! Took great care of our big, energetic dog. Would definitely book again (more)

from
$30
per visit
Confirmed availability: Labor Day
16.
On the move and ready to help!Washington Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking

About: Hello! My pet care experience started when I was in college when I was need of some income while going classes. My experience has been amazing becaus… (more)

from
$16
per visit
Calendar Recently Updated
17.
Your dog's new best friend!Douglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

About: In my neighborhood back home, I was the resident dog/house/baby-sitter for several years, especially as I got into high school and had more independe… (more)

from
$15
per visit
Calendar Recently Updated
18.
I’m walkin here! (boston accent)Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I definitely consider Taylor P special! Who gives someone else her flip-flops without another thought so one can walk to one's car on 95-degree steaming paveme… (more)

from
$17
per visit
19.
Loves animals— detail oriented!Kenwood, Chicago, IL, 60615
Drop-In Visits, Dog Walking

I made a last minute booking with Tracie and it was so easy to communicate and coordinate meeting up before hand to meet the cats and share keys. One of my cats… (more)

from
$17
per visit
Confirmed availability: Labor Day
Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Masheika took great care of our cats while we were away. She sent very detailed updates with pictures, and our cats warmed up to her immediately (they are usual… (more)

from
$32
per visit

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Grand Boulevard, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Grand Boulevard pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Grand Boulevard, Chicago who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

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 Grand Boulevard, 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: