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.

Confirmed availability
Memorial day
1. Todd

Home full-time - will love your pet

West Town, Chicago, IL, 60622

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Todd took great care of my pup! Will be back. (more)"

Confirmed availability
This weekend
2. Holly

Grad Student Home Full Time

Near North Side, Chicago, IL, 60610

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

8 repeat clients

"Holly was awesome with my dog Roo. She was very accommodating and helped me with pick up's and drop offs for daycare. She sent me pictures of Roo on walks an... (more)"

Confirmed availability
Memorial day
3. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

5 repeat clients

"Craig was communicative, took initiative with Arthur (play, Park, etc), very friendly, overall amazing! Hans is a wonderfully friendly dog too! (more)"

Confirmed availability
Memorial day
4. Diana

Home full time for your bff!

Near West Side, Chicago, IL, 60607

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

6 repeat clients

"Diana was awesome with Jojo on his first visit with her. She was patient with him and she took great care of him! We just moved to the city and feel a little... (more)"

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5. Kelyn

The Dawg Whisperer!

Near North Side, Chicago, IL, 60611

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Kelyn is an amazing dog-sitter. He's caring, responsible, and always very attentive to pets. He thoroughly enjoyed playing with my dog and made sure he got h... (more)"

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6. Tana

Quiet home with lots of cuddles

Loop, Chicago, IL, 60601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

21 repeat clients

"Tana is an excellent caregiver, really attentive to my dog's needs and in tune with handling a dog in the city. She has watched my pup for a few daycare sess... (more)"

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7. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"I recommend Alex to be a Dog walker and sitter on Rover since he is very punctual and always keeps his commitments. I am sure he will take great care of any ... (more)"

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8. Sera

Home full time &1-2 hrs in dogpark

Loop, CHICAGO, IL, 60601

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Sera did a great job watching our 11 month year old little Coco. Sera was very reliable and had excellent communication. She was flexible and accomodating ... (more)"

Confirmed availability
Memorial day
9. Pantira

Home full time, flexible schedules

Loop, Chicago, IL, 60601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

6 repeat clients

"Pantira was great! She was very accommodating and so sweet to my shy pup, Kinzie! And her Fluffy and Puffy were adorable and also welcomed Kinzie as well. ... (more)"

Confirmed availability
Memorial day
10. Kyisha

Home full time, large fenced back y

Englewood, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"It's a blessing having someone like Kesha around, she's very easy going with my dog, most of the time I have a hard time trying to get my dog to leave kesha,... (more)"

11. Ariel

Wags and Whiskers!

Lower West Side, Chicago, IL, 60616

Dog Boarding, Doggy Day Care

24 repeat clients

"Ariel was great! This was our 4 month old pup's first time away from us and she had a great time. We felt comfortable leaving her with Ariel and look forward... (more)"

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12. Elizabeth

Love doggies :) flexible schedule

Lower West Side, Chicago, IL, 60608

Dog Boarding, Doggy Day Care

7 repeat clients

"Elizabeth is amazing! She is incredibly responsive and super accommodating. Elizabeth sends pictures throughout the day and takes him on walks and runs! Love... (more)"

Confirmed availability
Memorial day
13. Tara

Care for your dog like my own

Bridgeport, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Tara is a wonderful and caring walker. She has walked and dog-sat my pup Biggie for the past 5 months and treats him like her own. I get pictures and updates... (more)"

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14. Emily

Downtown dog sitter.

Loop, Chicago, IL, 60605

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Great communication! (more)"

15. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Jeannette M Tom has been a caregiver for our beagle, Boomer. He walked, talked and ran with him. I trust him with all my pets! (more)"

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16. Waverly

Soon to be Dr.Wave!

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Doggy Day Care

22 repeat clients

"It was an absolute breeze to work with Waverly and I can tell she is fond of her fur buddies. Polo was worn out and slept well when I picked him the first da... (more)"

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17. Ekaterina

Home full-time - fenced yard

Bridgeport, CHICAGO, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ekaterina was amazing! My very anxious, somewhat shy dog just loved her! Ekaterina showed my dog lots of love and affection, took her for a couple of walks... (more)"

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18. Christie

Responsible dog handler

Near South Side, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

2 repeat clients

"Christie provided a great environment and fantastic updates for our puppy Frenchie Luna as she stayed all day. The pictures taken by Christie throughout the... (more)"

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19. Christal

I’m @ home full time

Kenwood, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi, I’m Christal and I am looking forward to being your next pet-sitter! I walked dogs professionally for years and have recently picked it back up... (more)

Confirmed availability
Memorial day
20. Nisha

Home full time. Dog lover!

Douglas, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: Full time masters student who loves pets especially dogs. Would like to get a dog someday after I finish my education. I love going on walks and ta... (more)

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: