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: Easter Weekend
Sitter Profile Image: Sophie R.
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Sitter Profile Image: Sophie R.
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1. Sophie R.

South Loop Based Pet Lover!
Loop, Chicago, IL, 60605
3.6 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
50 reviews
16 repeat clients
from
$50
per night

Sophie was wonderful and would highly recommend! She stayed at our home to watch our dog & cat and it was such a relief coming home knowing they were taken care of. Will definitely use her again in the future.

Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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2. 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! They sent an email update with a photo so we could see how it was going. They were also very responsive and flexible with the drop-off and pick-up time!

Confirmed availability: Easter Weekend
Sitter Profile Image: Kielyn J.
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Sitter Profile Image: Kielyn J.
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3. Kielyn J.

Your dog’s new guncle 🦄
Loop, Chicago, IL, 60605
3.7 mi. away
Boarding
5.0 out of 5 stars
5 reviews
1 repeat client
from
$70
per night

Kielyn was amazing with our Stella! He sent us pictures and updates throughout the weekend and made her feel comfortable. She typically is very anxious and will lose weight when we leave her, but not this time! We will definitely be booking with him again 😊

Confirmed availability: Easter Weekend
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
241 reviews
104 repeat clients
from
$45
per night

Elizabeth was great to work with and our pups had such a good time. Communication was great and we appreciated the photos during their stay. It’s nice to know there are good people out there! We are moving across the country so knowing the dogs were happy and safe during a stressful time was a relief.

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Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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5. 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
32 reviews
9 repeat clients
from
$50
per night

My dog has special needs and can be a lot to handle at times…Tania made me feel at ease while I was traveling and took such great care of Flash. I appreciate her patience and would recommend her to everyone I know.

Confirmed availability: Easter Weekend
Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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6. Rachel W.

Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
2.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
37 reviews
16 repeat clients
from
$55
per night

Rachel was an excellent sitter. She sent many pictures of my dog & took him to the dog park to socialize. Great communication skills & was available for drop off and pickup time when needed. I recommend Rachel to others looking for a reliable sitter.

Confirmed availability: Easter Weekend
Sitter Profile Image: Joye E.
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Sitter Profile Image: Joye E.
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7. Joye E.

Passionate about Pets.
Near South Side, Chicago, IL, 60605
3.2 mi. away
Boarding, House Sitting
5.0 out of 5 stars
28 reviews
10 repeat clients
from
$60
per night

Joye has watched Cliff 3 times and she is flexible, dependable and compassionate. For my most recent sit, I had to extend the time and drop off Cliff 3 days earlier and leave him an extra day because I was tending to a sick family member. Joye easily accommodated and was flexible as my dates changed. And, as always, she is amazing with Cliff. He is often sad when he comes back home because he misses her❤️

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Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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8. Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$55
per night

Kayla did a great job watching Mabel! She gave lots of updates and was very attentive. It was evident she really cares about the dogs she is watching. We would definitely rebook with her again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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9. 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
7 reviews
1 repeat client
from
$50
per night

This was the first time booking a pet sitter for my dog. Misti is very shy dog but since the first day she felt comfortable and happy with Ann-Marie. Good communication and constant updates. I will definitely leave my dog with her again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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10. 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
40 reviews
16 repeat clients
from
$52
per night

Ashley watched my baby while I was at work all day. He’s older now, has separation anxiety, can’t be left alone and has a grade 5 murmur so low stress is so important. He seemed to be having the best time with her!! I literally never leave him with anyone outside family anymore so this was a big step for us and I couldn’t have asked for any better.

Confirmed availability: Easter Weekend
Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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11. Viola R.

A dogs best friend
Grand Boulevard, Chicago, IL, 60615
1.3 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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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12. 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
$42
per night

Willy and Alexandra provided excellent care for my 70 lb Labrador. They exercised him frequently via walks and fetch, sent videos of him at play, and followed his medicine routine perfectly. Their fenced in yard ensured Julian could be outdoors all day without a worry. I recommend them without hesitation.

Confirmed availability: Easter Weekend
Sitter Profile Image: Morgan D.
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Sitter Profile Image: Morgan D.
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13. Morgan D.

Doodle lover & big exerciser!
Loop, Chicago, IL, 60601
4.4 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$70
per night

I had an excellent experience boarding Maverick with Morgan. She took him on multiple lake side walks and to the dog park during his stay with her. Maverick is a golden doodle and got along really well with Bear and they had several play dates. She took several pictures and videos and updated me all the time. I would definitely recommend her if you are staying in the loop. She’s the best !!!

Confirmed availability: Easter Weekend
Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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14. 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
10 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!

Confirmed availability: Easter Weekend
Sitter Profile Image: Erica T.
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Sitter Profile Image: Erica T.
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15. Erica T.

Bengal cat owner, love all cats
Loop, Chicago, IL, 60606
4.6 mi. away
Boarding
5.0 out of 5 stars
3 reviews
from
$40
per night

Erica is awesome. She dealt with my very picky, fussy Peri who was not having a good time adjusting to the different atmosphere. She was very patience, and therfore Peri felt comfortable enough to explore her surroundings. Pebbles looked to have had the time of her life although she was being a little aggressive with Alo. Erica dealt with it with patience and understanding. I know she had her hands full with these two at the same time. They are very different in personalities and aren't afraid to express it. Overall I swear my kitty's look better than when I dropped them off. Pebbles didn't even want me to take off her leash. Thank you again Erica for everything. You are awesome.

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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16. 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
11 reviews
5 repeat clients
from
$39
per night

Courtney has been consistently prompt in her communications and treated my Billie so well during her stay! Knowing that she had a playmate and was being kept in good care was a relief for me while I was out of town :)

Confirmed availability: Easter Weekend
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
9 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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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18. Masheika S.

Rover 101
All around animal lover 💜🐾
Grand Boulevard, Chicago, IL, 60653
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
21 repeat clients
from
$90
per night

Our pup’s second time staying with Masheika- he was so excited to go back! As before, she was very communicative and sent lots of pictures. Couldn’t ask for a better pet sitter.

Confirmed availability: Easter Weekend
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
30 reviews
12 repeat clients
from
$60
per night

I highly recommend Jake as a sitter! He’s been great with my dog Houna and I can tell she loves going there. She gets to play with other dogs and always comes home happy!

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Sitter Profile Image: Alexandra S.
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Sitter Profile Image: Alexandra S.
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20. Alexandra S.

Let me make your life easier!🐶🐾
Near West Side, Chicago, IL, 60607
5.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 repeat client
from
$70
per night

I have known Alexandra since we were kids. She is very responsible, honest, and hard-working. In the years that I have known her, Alex has had two dogs of her own and has always treated them with respect, kindness, and love. Additionally, I have seen Alex interact with my own dog and she was always sweet, friendly, and playful with him (he passed a few years ago). I firmly believe that Alex will provide safe, loving care and great customer service.

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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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