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

Calendar Recently Updated
Sarai O.
1.
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
Susan C.
2.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan is incredibly great! She accommodated my needs for Phoenix, and honestly, she’s so kind and generous. She’s even bought Phoenix a toy. Phoenix is just a p… (more)

from
$20
per visit
Calendar Recently Updated
Stephanie O.
Experienced vet assistant & fosterLower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Stephanie was so great and Azul loved her! I really appreciated how she communicated with me throughout her drop in visit with Azul and made sure I knew he was … (more)

from
$20
per visit
Jason C.
4.
Friendly dog walker from the UKLoop, Chicago, IL, 60605
Drop-In Visits, Dog Walking

I had to leave for a family emergency for the weekend. I had just adopted Priya the week before and really didn't want to board her. Thank God I found Jason! Ja… (more)

from
$15
per visit
Calendar Recently Updated
Skyler D.
5.
addictive dog lover with open armsDouglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
2 years of experience

About: Although I changed my career goal from being a veterinarian to a food journalist because of my love for food, dogs continue to be my FIRST LOVE! … (more)

from
$20
per visit
Calendar Recently Updated
6.
No ruff times, making a pet friend.Near South Side, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Dog Walking

Angel was amazing! She took good care of my babies, always sent updates, and tidied up the litter box space! Will definitely be asking for her to take care of t… (more)

from
$17
per visit
Calendar Recently Updated
reliable, trustworthy & caring!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Michaela is very good at handling animals and understanding their needs. She is honest, kind, disciplined, and punctual with her appointments. I would trust her… (more)

from
$17
per visit
Calendar Recently Updated
Loving MamabearBridgeport, Chicago, IL, 60616
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

I have 2 bullys ones 3 and ones only a year old and Marissa takes care of them while I am at work and when I am out of town. She makes sure they are walked dail… (more)

from
$20
per visit
Animal Science Student @ UIUCBridgeport, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Chase was awesome, super responsive, professional, and took great care of our cats while we were away. I would highly recommend Chase to anyone looking for pet … (more)

from
$30
per visit
Calendar Recently Updated
10.
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
11.
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
Calendar Recently Updated
12.
Energetic and Focused Pet CareWoodlawn, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking

Amazing!! Rebecca took such good care of our two cats while we were away. She brought a new toy and played with them, I felt so comfortable being away knowing t… (more)

from
$20
per visit
Calendar Recently Updated
13.
Enthusiastic CaretakerDouglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

About: I've taken care of dogs of every kind since I was 6. My parents and family have always had dogs so I have a great affinity towards dogs. I love the c… (more)

from
$20
per visit
14.
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
Calendar Recently Updated
Medical Student dog care!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Cristian was incredible!!! Communication with him was very clear and easy. He was reliable, on time, and very attentive of our dog's needs. Our dog is very anxi… (more)

from
$17
per visit
Calendar Recently Updated
Dog lover/babysitter for your pup!Hyde Park, Chicago, IL, 60615
Dog Boarding, Drop-In Visits, Dog Walking

Where to begin! Madeleine is one of the most genuine, hard-working, humble, accountable, and kind people that I know. Madeleine is engaged and incredibly devote… (more)

from
$16
per visit
Calendar Recently Updated
Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
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
$31
per visit
I'll love ur dog while you're away!Kenwood, Chicago, IL, 60615
Drop-In Visits, Dog Walking

Madeleine was amazing and she took great care of my cat. She also took some engaging photos and it was so nice to see what kitty was up to while we were away. H… (more)

from
$25
per visit
Calendar Recently Updated
19.
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
20.
Your dog will be my friendGrand Boulevard, Chicago, IL, 60607
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5 years of experience

About: I love dogs majorly. When I meet your dog he/she will be my friend and hopefully love me lol. I am a recent high school graduate from class of 2020. … (more)

from
$17
per visit

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: