Dog Boarding in Oakland, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Xue G.
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Sitter Profile Image: Xue G.
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1. Xue G.

Pawsitively Reliable Pet Sitter!
Near South Side, Chicago, IL, 60605
3.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$60
per night

Absolutely amazing host! We found Xue the last minute to take care of our labradoodle. Xue truly loves animals and our dog had a great time with her. Xue sent daily updates to us and we can see that our dog really enjoyed her time with Xue as Xue played with her and brought her to the dog park, which our previous hosts on Rover did not do. After we came back, our dog is happy as always. We are glad that Xue brought us back to Rover. Highly recommended!

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Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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2. Tania B.

Rover 101
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
4.1 mi. away
Boarding
5.0 out of 5 stars
33 reviews
9 repeat clients
from
$50
per night

Tania is the best! Our little guy is always so anxious, but he seems to do really well when staying with her. She is a great communicator and always sends lots of photos.

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Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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3. Ashley M.

Rover 101
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
41 reviews
18 repeat clients
from
$52
per night

Ashley was a wonderful sitter for my dog Lincoln! She was extremely communicative, walked Lincoln frequently and was so professional! Definitely would book with her again, thank you so much Ashley!!

Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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4. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
244 reviews
105 repeat clients
from
$45
per night

It was our first time using Rover and having Elizabeth watch our very energetic 8 month old Lab/Hound Pup. I cannot recommend highly enough the care that our dog Oliver received while we were gone. Elizabeth and her family took such loving care of our dog while we were away with lots of walks, snuggles, and a few treats too :) Thank you for watching our pup while we were gone and I know next time we are away Oliver will be so happy to spend time with his new friends!

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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5. Courtney B.

Your Dog's Favorite Sitter
Grand Boulevard, CHICAGO, IL, 60653
1.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
16 reviews
5 repeat clients
from
$39
per night

My dog immediately gravitated towards Courtney's calm and caring demeanor which let me know my dog would do well in her care! Like any dog owner, ensuring that my dog is safe, happy, and comfortable while on vacation is a top priority. Courtney provided prompt communication, daily updates, and made sure my dog felt right at home. I would rebook again! If you are looking for quality care for your dog, do not hesitate to book with Courtney! :)

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Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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6. Andrew T.

WFH Couple, Park Nearby
Lower West Side, Chicago, IL, 60608
4.4 mi. away
Boarding
5.0 out of 5 stars
99 reviews
41 repeat clients
from
$45
per night

Andrew and his SO treated Milo with so much love! Multiple walks a day and send updates daily! We will definitely be using them in the future.

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Sitter Profile Image: Jennifer N.
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Sitter Profile Image: Jennifer N.
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7. Jennifer N.

Not Just a pet,a family favorite.
Lower West Side, Chicago, IL, 60608
4.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
95 reviews
60 repeat clients
from
$45
per night

Jennifer was a savior during my short notice holiday getaway. My pup is shy and somewhat anxious, and she recognized that while allowing him to be himself. She's responsive and sends cute photos and videos of the pups.

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Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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8. Ebonee A.

12 + years of Vet-Tech experience!
Hyde Park, Chicago, IL, 60615
2.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
30 reviews
14 repeat clients
from
$50
per night

My puppy (Beau) had an amazing time with Ebonee. She was very communicative and sent pictures/videos daily. He seemed to be really calm and happy during his stay with Ebonee. ?

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Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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9. Rachel W.

Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
39 reviews
16 repeat clients
from
$60
per night

Rachel was AMAZING!! She took such great care of our Shelby. She was extremely accommodating with drop off and pick up. Rachel's dog, Addy, was so sweet and Shelby enjoyed her time with her. We hope Rachel is available the next time we are out of town.

Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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10. Ashley B.

Open house for Pets
Hyde Park, Chicago, IL, 60615
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
72 reviews
38 repeat clients
from
$75
per night

Ashley is very professional, gives great updates about your pup, and takes the job of caring for your pet seriously! 10/10, would strongly recommend.

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Sitter Profile Image: Gillian K.
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Sitter Profile Image: Gillian K.
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11. Gillian K.

Loves long walks and fluffy friends
Bridgeport, Chicago, IL, 60608
3.3 mi. away
Boarding
5.0 out of 5 stars
17 reviews
7 repeat clients
from
$40
per night

Oliver had a great first stay with Gillian. She was super responsive and kept us updated with pictures throughout the week. Would definitely recommend Gillian and will not hesitate leaving Oliver with her again.

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Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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12. Katie M.

Long time animal lover
Near North Side, Chicago, IL, 60610
5.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
154 reviews
51 repeat clients
from
$45
per night

Katie was amazing and took great care of my pups needs and provided updates during a longer stay. Java was very welcoming as well, and we look forward to booking next time with them.

Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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13. Ann-Marie H.

Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
2.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$50
per night

Ann-Marie took great care of my fur baby while I was out of town. She sent pictures throughout the stay, maintained communication, and was flexible when we pushed our return to a later time. I would definitely recommend her and look forward to hiring her again in the future.

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Sitter Profile Image: Briana V.
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Sitter Profile Image: Briana V.
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14. Briana V.

Always home, 24/7 attention & care!
South Lawndale, Chicago, IL, 60623
5.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
45 reviews
11 repeat clients
from
$48
per night

Another visit with a Great sitter! I’m so impressed with how much love and patience Briana has with my little guy Max. She was nonstop with updates and pictures which really eased my nerves. I will definitely book with Briana again and again.

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Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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15. Willy J.

Reliable Dog Lover at your Service
Douglas, Chicago, IL, 60653
1.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
15 reviews
3 repeat clients
from
$47
per night

Very accommodating, even for a last minute request. Kept me updated on things that could be of concern (my girl refused to eat because she’s dramatic) and sent pics/videos throughout the stay! Would recommend. Thank you again

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Sitter Profile Image: Yanely O.
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Sitter Profile Image: Yanely O.
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16. Yanely O.

All animals are equal!
Bridgeport, Chicago, IL, 60608
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
4 repeat clients
from
$50
per night

She took very good care of my dogs, and they seem to enjoy themselves. She was very accommodating and helpful.

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Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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17. Makeba L.

WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
13 reviews
10 repeat clients
from
$47
per night

Makeba was amazing! I had to book for boarding SO last minute because of a sitter cancellation but she was very accommodating with schedules and pet care and was also very quick in responding and had awesome communication. She was able to take my dog out on frequent walks and pee breaks and always sent me pictures to update on how he was doing which made me feel reassured he's having a good time. My dog loved staying with her, I would recommend to family and friends.

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Sitter Profile Image: Regan D.
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Sitter Profile Image: Regan D.
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18. Regan D.

Your friendly neighborhood pet girl
Near North Side, Chicago, IL, 60654
4.9 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
33 reviews
13 repeat clients
from
$45
per night

Regan and her boyfriend were great with Penny! They sent me lots of photo updates and Penny got plenty of time with them at home / watching Sunday football. Penny enjoyed her stay and I felt very comfortable that she was in good hands.

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Sitter Profile Image: Jake W.
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Sitter Profile Image: Jake W.
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19. Jake W.

Pets are humans too!
Near North Side, Chicago, IL, 60611
4.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
31 reviews
12 repeat clients
from
$60
per night

Jake was great with Lincoln. He followed our date instructions and sent a ton of pics throughout the weekend. Lincoln was extra excited to play with Jake’s puppy too. Every pic he sent, Link was smiling. Highly recommend.

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Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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20. Kyle H.

Rover 101
Over a decade of experience!
Hyde Park, Chicago, IL, 60615
1.9 mi. away
Boarding
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$55
per night

Kyle and Ben were great! Our dog loves them and seems to have had a great time with their dogs and cats. Kyle and Ben board many dogs in our neighborhood and everyone has great things to say about them. It was relief to know our dog was in a home environment with nice, trustworthy people.

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Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 7915 owners have reviewed sitters in Oakland, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect dog sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average dog boarding rates to get an idea before you start a conversation with a dog sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Oakland dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Oakland, Chicago, IL who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Oakland.

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