Doggy Day Care in Oakland, Chicago

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

Calendar Recently Updated
Dionne C.
1.
Furry Friend Extraordinaire!Woodlawn, CHICAGO, IL, 60637
Dog Boarding, Doggy Day Care

I do not know where to begin with this experience!!! Dionne has been phenomenal!! My fur baby attends day care and by day 2 he was whining to get out of the car… (more)

from
$35
per day
Calendar Recently Updated
David N.
2.
NOT JUST A PET BUT FAMILYLower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care

David was great with Butters. He made sure I was 100% comfortable leaving her for the first time and let me tour the place before committing. My dog is no longe… (more)

from
$30
per day
Calendar Recently Updated
Jacqueline D.
Dog lover looking to help out!Near North Side, Chicago, IL, 60654
Dog Boarding, Doggy Day Care

Jacqueline has always been an animal lover and growing up with our family Brittany, chestnut she was alway amazing. Gentle, loving and caring, she always was re… (more)

from
$33
per day
Calendar Recently Updated
Mary M.
4.
Here to shower your dogs with love~Loop, Chicago, IL, 60601
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Rupert’s stay with Mary was a success! I received updates and pictures throughout the day. Rupert looked super happy and comfortable. He especially seemed to en… (more)

from
$30
per day
Calendar Recently Updated
Cody F.
5.
A pup-cation to remember!Loop, Chicago, IL, 60604
Dog Boarding, Doggy Day Care

Cody is a true dog lover and he has been around dogs his whole life. Cody’s dog “Hopper” adores Cody and they have an amazing owner/pet relationship. Cody is… (more)

from
$30
per day
6.
Loving care when your not there!!West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I have cats Nataya has meet and watched.she was very kind and gentle with them and was able to make them comfortable.I would recommend her.Her love and care for… (more)

from
$40
per day
Calendar Recently Updated
Animals are love, they are lifeLower West Side, Pilsen, IL, 60608
Dog Boarding, Doggy Day Care, Dog Walking

About: I've taken care of animals of all kind since i was around 8 years of age. I've always felt i had a special connection with them my whole life, I've n… (more)

from
$35
per day
Calendar Recently Updated
I'll run with your dog!Loop, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Andrea was great! She sent updates throughout the day and kept my girl busy. I’d highly recommend her to anyone. Zora had a blast with Andrea! (more)

from
$45
per day
Confirmed availability: Memorial day
9.
Couple family pet townhouse w/ yardNear South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care, Dog Walking

Liyu and his pets are so friendly! He would always have his dog around him everywhere he go. There isn’t a day I seen Liyu without His dog. (more)

from
$40
per day
10.
Buying happiness= getting a puppy:DHyde Park, Chicago, IL, 60615
Dog Boarding, Doggy Day Care, Dog Walking

All I can say is....AMAZING! I let her watch my dog for the weekend and they had the best time! All the pictures she sent were ADORABLE I would defitely reccomm… (more)

from
$40
per day
Calendar Recently Updated
Dog lover - WFH!Loop, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hello, my name is Jennifer. I’m an accountant living in an extremely pet friendly apartment with a park located 5-10 minute walk from it. I’ve dog sa… (more)

from
$32
per day
Calendar Recently Updated
Your dog is my dog!!Near West Side, Chicago, IL, 60607
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jonathan was great! We needed a sitter in a pinch and he was very responsive, friendly, and accommodated us easily. (more)

from
$40
per day
13.
Weekends I’m Open, Dog Walk lover.Near South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

Cori was Everything you could want in a dog sitter. I truly felt like she was excited to see my dog and take care of him as though he was her own. I got prompt … (more)

from
$45
per day
Calendar Recently Updated
14.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan watched my dog for years and he was always thrilled to stay with her. We always joked that if reincarnation was possible, we wanted to come back as Sus… (more)

from
$35
per day
Calendar Recently Updated
15.
Let the PAWS combineDouglas, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

Shivani is a good dog owner already. She is very committed to her pet's life and accecpts the responsibility. She takes good care of pets regarding their health… (more)

from
$35
per day
16.
Lakefront, parks, beach & dog parkHyde Park, Chicago, IL, 60615
Dog Boarding, Doggy Day Care

Janet was great with my puppy! She is super personable and thoughtful, and made sure to take the time to ask about what he needed for a comfortable stay. I also… (more)

from
$40
per day
Calendar Recently Updated
17.
Flexible and Reliable Fun timeBridgeport, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

About: Hi there! This is G. I am currently a masters of biology student at IIT, and also a proud dog owner! I spent most of my free time with my buddy Kimi,… (more)

from
$30
per day
18.
Dogs are a humans bestfriend.Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Roxy is a very responsible dog walking always on time very dependable she took very good care of my dog when she toom my dog on walks my dog loves her walks wit… (more)

from
$33
per day
Calendar Recently Updated
19.
Plenty of long walks and treats!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jasmine was available on short notice (day before) and Moose was so happy when I picked her up. She walked Moose and sent pictures and check ins all day. (more)

from
$33
per day
Calendar Recently Updated
20.
Dogs are four legged best friendsGrand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Pamela is a wonderful dog owner and caregiver. She is a yorkie mom and loves to interact and spoil her baby. Seeing her interact with other dogs makes me realiz… (more)

from
$45
per day

Rover also offers Doggy Day Care in:

Dog owners in Oakland, Chicago, IL turn to day care sitters on Rover.com for their doggy day care needs. Over 7,915 pet owners have reviewed day care sitters in Chicago, giving them an average rating of 4.9/5. Doggy day care can be affordable, no matter where you live or what your price range may be. Curious about how much doggy day care costs in Chicago with Rover.com? Check out our average doggy day care rates near you to get an idea before getting a conversation started with a day care sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

With Rover, you can find a trustworthy, loving pet sitter to take care of your dog while you're at work or have a day full or errands. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 60,000 sitters who've listed their services on Rover. That way, you're sure to find a doggy day care who's right for your needs. We're proud that 95% of our sitters have 100% 5-star reviews, and we think your dog will love them too. Search for a sitter who offers doggy day care, schedule a Meet & Greet, and book the stay if it seems like a good fit. No matter how often you need day care, you're sure to find a sitter who will treat your dog like family. And just like with overnight services booked on Rover, doggy day care is covered by premium insurance, at no extra charge to you.

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: