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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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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1. 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
245 reviews
106 repeat clients
from
$45
per night

E has a lovely home and yard well-suited to caring for dogs. E kept us updated on Kodi's status throughout our vacation, setting our minds at ease. Thanks!

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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
34 reviews
9 repeat clients
from
$50
per night

Tania took great care of Cookie and went above and beyond to keep her happy while we were gone for 10 days! She got her food, treats and even a new coat! We will definitely board Cookie with Tania again and highly recommend her as a dog sitter!

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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
44 reviews
19 repeat clients
from
$52
per night

Ashley went above & beyond watching my dog, Pippa. She was so attentive, communicative, personable, and a joy to talk to. I would highly suggest her to watch your fur baby! Thank you Ashley!!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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4. 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

Ms. Makeba was great with my fur baby, she sent pictures everyday and gave me updates while my senior baby was in her care. Thank you so much for taking care of my Chole. I will definitely be calling on you again Ms Makeba.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Xue G.
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Sitter Profile Image: Xue G.
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5. 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
23 reviews
7 repeat clients
from
$60
per night

Very nice and understanding with good communication; Xue took good care of my cat Pound Cake with multiple daily updates as if he was her own cat while I was out of town for almost 2 weeks. I highly recommend her :)

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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
102 reviews
42 repeat clients
from
$45
per night

Andrew is great! I boarded Stitch with him for a couple of nights and Andrew periodically sent pictures and videos of Stitch having a blast! I highly recommend him

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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7. Courtney B.

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

Courtney was just wonderful! We left over the holidays and she kept up great communication with updates and lots of photos. She followed all our instructions to a tee and our boy was all smiles when we picked him up. Definitely recommend a stay with Courtney, she's the best!

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Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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8. 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
10 reviews
2 repeat clients
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: Gillian K.
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Sitter Profile Image: Gillian K.
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9. Gillian K.

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

Our third time using Gillian’s pet sitting services and it was fantastic as usual! My dog is always so happy to come here, and Gillian does such a great job keeping us posted with silly photos. This time around my dog decided to hurt her paw days before my trip, but Gillian put my mind at ease with following her new medication routine and giving me updates on how her paw was doing.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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10. 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. ?

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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11. 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
40 reviews
16 repeat clients
from
$60
per night

Our dog had a great time! We got lots of pictures and updates. They live close to a dog park and he got a lot of exercise. Flexible and friendly.

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Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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12. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jennifer N.
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Sitter Profile Image: Jennifer N.
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13. 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
105 reviews
61 repeat clients
from
$50
per night

Even tho it was a last minute request, Jennifer went up and beyond to take care my dog Maverick. Began with asking questions when dropping Maverick to get to know him and understand his needs. Keep me updated and sent a video. I definitely recommend Jennifer and will use again soon. If Maverick could talk I will say he definitely felt comfortable and had a good time..

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Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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14. 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
158 reviews
54 repeat clients
from
$45
per night

Katie and Java did a good job sending photos and updates. Katie is pleasant to work with and was flexible in allowing me to pick up my dog a day early. Thank you Katie !

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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15. Viola R.

A dogs best friend
Hyde Park, Chicago, IL, 60615
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$30
per night

Viola did a fantastic job on taking care of my Zoë. She sent updates and pictures of everything that she had been doing for Zoë. I saw how comfortable she made Zoë feel being in her care. I will definitely have Viola to take care of Zoë again whenever Viola is available.

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Sitter Profile Image: Regan D.
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Sitter Profile Image: Regan D.
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16. 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
34 reviews
13 repeat clients
from
$45
per night

Regan and Adam were so good with Gigi! Gigi is sometimes reactive towards other dogs and can’t be in close proximity when on leash. She takes a couple medications for anxiety to help with that reactivity. We have been lucky enough to have family close by to be able to watch her for the past 4 years when we go out of town, but this time none of our family was available so that’s when we found Regan! We did a quick meet and greet to go over Gigis anxiety and meds. They did such a good job at giving updates and sending lots of pictures for the week we were gone. We have never seen Gigi sad to leave family house when being dog sat, but she was so sad to leave Regan and Adam’s place! Will definitely be reusing them as sitters in the future! Can’t recommend them enough!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Briana V.
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Sitter Profile Image: Briana V.
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17. 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
46 reviews
12 repeat clients
from
$48
per night

Briana has sat for my dog Kodi a couple times and she is an excellent sitter. She always sends me updates and pictures throughout his stay and he always comes back home happy, healthy and full of energy. I can count on Briana to stick to his feeding and walking schedule as instructed. Kodi looks forward to visiting with Briana and her 2 dogs again in the near future. Thanks again Briana!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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18. MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
2.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
12 reviews
1 repeat client
from
$40
per night

My dog was taken care off even though she is particular with her habits. María José always keep me updated and made me feel good and at easy while I was out of town. Thank you!

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Sitter Profile Image: Dion F.
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Sitter Profile Image: Dion F.
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19. Dion F.

Your baby’s favorite hotel 🐕🦴
Near West Side, Chicago, IL, 60661
4.5 mi. away
Boarding
5.0 out of 5 stars
6 reviews
from
$50
per night

It’s always a little nerve wracking when you’re away from your pup for an extended period, but Dion was great with Brix! He was patient, kind, communicative and gave him plenty of long walks which we appreciate. Will be utilizing Dion in the future when needed :)

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Sitter Profile Image: Sasha Z.
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Sitter Profile Image: Sasha Z.
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20. Sasha Z.

Trustworthy & Honest
Near North Side, Chicago, IL, 60563
5.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
5 repeat clients
from
$45
per night

Sasha was the perfect sitter!!! She sent so many pics and updates and was so sweet and understanding when my flight was delayed. Thank you so much Sasha!!! I would 100% bring Yogurt back to stay with Sasha. :)

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Rover also offers Dog Boarding in these neighborhoods:

Rover also offers other services in Oakland:

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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