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.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: E K.
Sitter Profile Image: E K.
1.
E 
Verified Background Check
Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Elizabeth was a pleasure to deal with from first contact until we picked Tika up at the end of the night. Amazing communication and pictures. (more)

from

$40

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ashley B.
Sitter Profile Image: Ashley B.
2.
Open house for Pets
Hyde Park, Chicago, IL, 60615
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Ashley was awesome with Hazel! She kept us up to date on Hazel throughout her stay and sent pictures. We should absolutely recommend her and her husband! (more)

from

$35

per day
Calendar Recently Updated
Sitter Profile Image: Pauline A.
Sitter Profile Image: Pauline A.
Your furry baby’s second mom
Loop, Chicago, IL, 60605
Boarding, Doggy Day Care

Pauline was my first experience on Rover with my 10 week old lab puppy. She was very quick to respond, gave frequent updates, and was patient and kind when my p… (more)

from

$35

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Jumari H.
Sitter Profile Image: Jumari H.
4.
Ever seen a dog smile?🙃
Grand Boulevard, Chicago, IL, 60653
Boarding, Doggy Day Care, Dog Walking

About: New Rover clients can use promo code JUMARH69827 for $20 off their first booking I’ve taken care of dogs of every kind since I was 18. Friends an… (more)

from

$38

per day
Calendar Recently Updated
Sitter Profile Image: Marissa W.
Sitter Profile Image: Marissa W.
Loving Mamabear
Bridgeport, Chicago, IL, 60616
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Marissa was great with our animal. She has a warm and caring personality. I felt comfortable leaving my cat in her care. If you're in need of a sitter, please c… (more)

from

$40

per day
Calendar Recently Updated
Sitter Profile Image: Susan C.
Sitter Profile Image: Susan C.
6.
You're Dog is My Dog!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan did an amazing job taking care of Clara! She was incredibly prompt at replying to all of my messages and questions, and sent lots of photos during Clara's… (more)

from

$35

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ra'eesa S.
Sitter Profile Image: Ra'eesa S.
Extraordinary pet care! :)
Woodlawn, Chicago, IL, 60637
Boarding, Doggy Day Care, Dog Walking

About: I've cared for dogs and other pets since I was a kid. I've had the opportunity to love dogs, hampters, birds, and cats! I am and have always been rel… (more)

from

$35

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Jamie & Ritz W.
Sitter Profile Image: Jamie & Ritz W.
WFH dog parents, pet friendly home
Near South Side, Chicago, IL, 60605
Boarding, Doggy Day Care

Jamie was very responsive and gave updates while watching my dog. Highly recommend them to watch your pet! (more)

from

$40

per day
Calendar Recently Updated
Sitter Profile Image: Cindy & Cesar M.
Sitter Profile Image: Cindy & Cesar M.
Making time apart easy for you both
Near South Side, Chicago, IL, 60616
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Cindy is the most reliable and loving person I know. I think it speaks volumes that her own dogs are the most well behaved, respectful, happy and healthiest dog… (more)

from

$38

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ariana C.
Sitter Profile Image: Ariana C.
10.
It’s a Pawty!
Lower West Side, Chicago, IL, 60608
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Ariana is a fantastic human and even better pet caregiver. She has watched my pit bull on and off for 3 years and makes it so easy to trust. I definitely recomm… (more)

from

$33

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Holly R.
Sitter Profile Image: Holly R.
11.
Your Dog’s WFH Bestie
Woodlawn, Chicago, IL, 60637
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

We had a great first visit with Holly for doggy day care. She is a clear communicator and put me at ease with her experience with dogs. My pup loved the big yar… (more)

from

$48

per day
Calendar Recently Updated
Sitter Profile Image: Daniella M.
Sitter Profile Image: Daniella M.
Remote Worker, Full of Energy!
Loop, Chicago, IL, 60605
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Daniella is wonderful with our lab mix. She took the time to read over his profile, asked lots of questions to make sure she understood his needs and our prefer… (more)

from

$33

per day
Sitter Profile Image: Maria C.
Sitter Profile Image: Maria C.
13.
Double lot yard adores dogs
Chicago Lawn, Chicago, IL, 60629
Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Maria is so nice. She took very good care of my pup. She's responsive, sends updates, sends pics, and very knowledgeable about dogs. Will use her again. (more)

from

$30

per day
Calendar Recently Updated
Sitter Profile Image: Ericka J.
Sitter Profile Image: Ericka J.
14.
Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ericka is an exceptional person who loves animals! If one were to overhear our conversations they would think we were talking about the "human" love of our live… (more)

from

$35

per day
Calendar Recently Updated
Sitter Profile Image: Lauren I.
Sitter Profile Image: Lauren I.
15.
I never have too many furry friends
West Town, Chicago, IL, 60642
Doggy Day Care

Amazing communication! Understanding of a new puppy parent with a puppy new to daycare as well. You can't pay for peace of mind. Lauren was kind, accommodating,… (more)

from

$20

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ashley M.
Sitter Profile Image: Ashley M.
16.
WFH, Pet Loving, Porch, Park!
Lower West Side, Chicago, IL, 60608
Boarding, Doggy Day Care

Ashley was very good to Jace. She made sure he had plenty of exercise and play time outside and he came back a happy boy:) (more)

from

$32

per day
Calendar Recently Updated
Sitter Profile Image: Jake W.
Sitter Profile Image: Jake W.
17.
Pets are humans too!
Near North Side, Chicago, IL, 60611
Boarding, Drop-In Visits, Doggy Day Care

Terrific experience! Jake made it happen within 30 minutes of contact. Curbside drop off and pick up. My dog came home happy and exhausted. (more)

from

$33

per day
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Brianna F.
Sitter Profile Image: Brianna F.
18.
Animal lover, works from home!
Lower West Side, Chicago, IL, 60608
Drop-In Visits, Doggy Day Care, Dog Walking

Brianna is a wonderful pet sitter! She took care of my two cats while I was away for a week. They were kept clean, nicely groomed and well fed. She provided me … (more)

from

$33

per day
Calendar Recently Updated
Sitter Profile Image: Kaylynn P.
Sitter Profile Image: Kaylynn P.
19.
Lover of pups and exercise
West Town, Chicago, IL, 60642
Drop-In Visits, Doggy Day Care, Dog Walking

Goose loves spending time with Kaylynn and Blu! Our schedule has been a little crazy this spring and Kaylynn has been so understanding whenever we need to modif… (more)

from

$38

per day
Calendar Recently Updated
Sitter Profile Image: Alyssa G.
Sitter Profile Image: Alyssa G.
20.
Your dog's new best friend!
Loop, Chicago, IL, 60607
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Having known Alyssa for a long time, she is an experienced, dog-loving person. I am extremely satisfied with her care for our dog and would highly recommend he… (more)

from

$45

per day

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:

Doggy Day Care