Pet Sitting & Drop Ins in Oakland, 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: 4th of July
Susan C.
1.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Hi. Susan is a very loving person and adores animals. I've seen her interact with many, always if a very caring and careful way. She keeps her house immaculate.… (more)

from
$20
per visit
Calendar Recently Updated
Matt C.
2.
A Pawfect Pet ExperienceKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Matt has stayed with my dog several times. My dog is high energy and requires a lot of ball and play time. Matt rose to the occassion, spending hours outside … (more)

from
$20
per visit
Calendar Recently Updated
Azalia M.
3.
Experienced Vet Assistant :)Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Azalia has been an absolute blessing!   Mocha and Olive   (Our dogs ) loves Azalia and they do a happy dance upon her arrival.  She is prompt, reliable, trustwo… (more)

from
$17
per visit
Calendar Recently Updated
Tiffany L.
Caring for all animals big or smallBridgeport, Chicago, IL, 60609
Drop-In Visits, Dog Walking

If you want someone who is caring, loving and will treat your animal(s) as their own then Tiffany is your person. Tiffany is my go-to person anytime I need some… (more)

from
$17
per visit
Confirmed availability: 4th of July
Treonna F.
Treats, toys and hugs.Woodlawn, Chicago, IL, 60637
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

I’ve known Treonna for 6 plus years and for as long as I’ve known her she has always been in love with animals. I’ve watched her take care of dogs who were in a… (more)

from
$15
per visit
Calendar Recently Updated
6.
Dogs are a humans bestfriend.Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Roxy was responsive, arrived as scheduled, and checked on our pets as requested. I also appreciate Roxy bringing in our mail packages that were left at the door… (more)

from
$20
per visit
7.
Flexible schedule, big fenced yard!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Maeve was great! Very nice and easy going. You can tell she enjoys animals. Luna love her upon meeting her and her communication was great with photos and video… (more)

from
$20
per visit
Calendar Recently Updated
Pets need loving care alwaysKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Christina is great! She took excellent care of my two cats while I was out of town. Her updates were very detailed with lots of pictures, and the cats loved her… (more)

from
$16
per visit
Calendar Recently Updated
Animal LoverHyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Allyssa was great with my cats while I was away for the last week. She spent time with them, making sure they had quality timeworn someone, as well as having en… (more)

from
$20
per visit
Confirmed availability: 4th of July
10.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

I highly recommend Annie to anyone with both cats & dogs who wants their pet to be treated with care. Annie is communicative, polite, punctual, and went above a… (more)

from
$25
per visit
Confirmed availability: 4th of July
Vaccinated animal lover. :)Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Masheika was wonderful! She communicated great and took care of our cat for over two weeks in our home. We got pictures everyday too! We forgot to cover our cou… (more)

from
$25
per visit
Calendar Recently Updated
12.
Animals are my joy.Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

About: Hello! I have grown up with pets. I've been around them since before birth. Risking sounding a bit antisocial, I'll admit that I love animals more th… (more)

from
$17
per visit
Confirmed availability: 4th of July
13.
Ready to greet and treat your pup.Douglas, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Ashley is great with our dog, Shea — I cannot recommend her enough! She cares for my girl as if she were her own. She always goes above and beyond and I never … (more)

from
$20
per visit
14.
Hanging with your pet > My real jobBridgeport, Chicago, IL, 60609
Drop-In Visits, Dog Walking

We had Haley do a couple drop in visits for our kitten, Tiger, while we were away. Haley arrived on time to our house for our first meeting and was so kind and … (more)

from
$20
per visit
Calendar Recently Updated
15.
Experienced dog lover!Hyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking

Lilia was great!! She took the cutest photos of my cat while I was out of town and took the time to play with her :’) great communication on her end. (more)

from
$17
per visit
16.
Your Dog Will Love Me!Grand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Alex was amazing. (more)

from
$16
per visit
17.
Over 10 years of dog experience!Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Katja took great care of my Lola. I could tell by the pictures how happy she was! I really appreciated the detailed reviews, as well. Would book her again! (more)

from
$20
per visit
Calendar Recently Updated
18.
Love spending time with your petKenwood, Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking

Daniel took care of my puppy when I was out of town and he did a great job! He is very caring and made sure he got tons of attention. It was reassuring to have … (more)

from
$17
per visit
Confirmed availability: 4th of July
19.
Dogs are four legged best friendsGrand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I love Pamela! She’s an awesome person with a beautiful personality. She’s very kind, sweet, and respectful. She considerate and has the cutest dimples and smil… (more)

from
$30
per visit
Hyde Park’s purrfect pet sitter!Kenwood, Chicago, IL, 60653
Drop-In Visits

Victoria came over for a meet and greet and both my dog and cat immediately liked her. She came during the agreed upon times and took my dog for a nice walk. Wi… (more)

from
$15
per visit

Rover also offers Pet Sitting & Drop Ins in:

Dog lovers in Oakland, Chicago, IL love pet sitters on Rover.com. Over 7,915 pet owners have reviewed pet sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Chicago can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakland, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Oakland, Chicago who can provide the care your pet needs, when they need it.

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:

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 Oakland, 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: