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

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Sitter Profile Image: Yingyue L.
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Sitter Profile Image: Yingyue L.
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1. Yingyue L.

Streeterville WFH doggy lover
Near North Side, Chicago, IL, 60611
4.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
2 repeat clients
from
$45
per day

Yingyue was accommodating, responsive, and took great care of Baxter. He is a senior and needs many potty breaks; she took him out multiple times and sent me pics and messages to let me know how he is doing throughout the day. This was the first time but definitely not the last time Baxter will be staying w Yingyue. I highly recommend her to anyone looking for a responsible and caring pet sitter for their fur baby.

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Sitter Profile Image: Judy D.
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Sitter Profile Image: Judy D.
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2. Judy D.

Pet loving
Near North Side, Chicago, IL, 60654
5.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$38
per day

Judy took great care of our dog! He can be anxious with strangers but seemed to settle in fine

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Sitter Profile Image: Morgan D.
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Sitter Profile Image: Morgan D.
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3. 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
16 reviews
4 repeat clients
from
$50
per day

Morgan was great with Pepper! She sent a bunch of photos and videos throughout the day and was very attentive. She asked questions to make sure she was filling Pepper’s needs. She had such a great time that when I picked her up she kept looking back for Morgan because she didn’t want to leave. Would 100% recommend and use Morgan again!

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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 day

Liz and her family are ideal pet sitters. My bulldog Daffodil became comfortable quickly and is not eager to leave their home at the end of the day due to the abundant personal attention she receives. Great indoor and outdoor space. Consistent updates and photos. I think Daffodil has found a 2nd family, a home away from home, if you will.

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Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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5. 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
19 repeat clients
from
$38
per day

Ashley and her daughter Marina are incredibly conscientious and caring. Every time I bring my dog to their place, he is excited to run up the stairs and be reunited with his extended family. He truly loves them, and I can see how much they love him as well. 10/10, would recommend Ashley’s services to anyone!

Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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6. 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
$50
per day

Ashley did such a great job with our 5 month old puppy! She made sure Connie felt safe and comfortable during one of our first times away from her, and Connie returned home tuckered out from a great day of play.

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Sitter Profile Image: Lisa H.
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Sitter Profile Image: Lisa H.
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7. Lisa H.

Extended family to your fur babies
Loop, Chicago, IL, 60607
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$46
per day

Lisa and her husband were incredible dog sitters. They have a very friendly dog of their own and he got along great with our puppy. Taking care of a puppy is a lot of work and they took her on lots of walks and played with her all day. They were super responsive and lovely. 5 stars! Would absolutely recommend

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Sitter Profile Image: Coraihma S.
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Sitter Profile Image: Coraihma S.
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8. Coraihma S.

✨ Dogs are my kinda people ✨
Lower West Side, Chicago, IL, 60608
3.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
5 reviews
4 repeat clients
from
$40
per day

About: Hi! My name is Cory and I live in Pilsen with my 12 year old poodle mix Abbey. I’ve had Abbey since she was 2 months old and we’ve been inseparable since. I am a huge animal lover and would love to care for your furbaby/furbabies. I love to keep Abbey pretty busy even at her age we do lots of long walks, lots of enrichment, will occasionally visit the small dog park near us to allow her to socialize with other dogs. She loves all humans, dogs and cats and would love to have a little companion visiting us! 🐾 I work from home 3-4 days of the week and am readily available to feed them and take them out on their same schedule to make their stay as comfortable as possible Dogs are welcomed to roam the entire house as they want. I will walk your dog every couple hours and make sure they are comfortable

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Sitter Profile Image: David R.
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Sitter Profile Image: David R.
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9. David R.

Stay at Home Lawyer + Dog Dad
Loop, Chicago, IL, 60605
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
155 reviews
50 repeat clients
from
$57
per day

David and his fiancé were great with Leo. They took him on multiple walks and made sure that he was happy and cared for at all times. They also have the sweetest dogs that became best friends with Leo and kept him entertained. Thank you David!

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Sitter Profile Image: Jamie & Ritz W.
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Sitter Profile Image: Jamie & Ritz W.
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10. Jamie & Ritz W.

WFH dog parents, pet friendly home
Near South Side, Chicago, IL, 60605
3.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
28 reviews
11 repeat clients
from
$50
per day

Jamie & Ritz are wonderful guardians to Maeve. They consistently throughout the day kept me posted on how she’s doing, and Toffee made her feel very welcome in their home. I highly recommend, and I plan to rebook with them again!

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Sitter Profile Image: Xue G.
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Sitter Profile Image: Xue G.
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11. 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
$50
per day

Xue was super excited and took good car of my dog, She responded quickly and was available on a very short notice. Definitely would repeat.

Sitter Profile Image: Vick D.
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Sitter Profile Image: Vick D.
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12. Vick D.

I'll get on your dogs level.
Bridgeport, CHICAGO, IL, 60608
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4.5 out of 5 stars
16 reviews
6 repeat clients
from
$40
per day

Vick is the best! Flexible, easy to communicate with, super nice, dependable, thoughtful, and caring! Best of all, he treated my old, anxious, nearly blind dog with kindness and expertise. She really loved staying at his house. It's obvious that he really loves and understands dogs. He's an amazing dog sitter. Thank you!

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Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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13. 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
$42
per day

Make a is the best!! I fell very comfortable with Makeba caring for Champ.

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Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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14. 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
$35
per day

Willy was amazing with my pup! I love that he has the skill to assist me with my 11wk pup with potty training. Very attentive with my baby and a lot of play time! Love the consistency with the updates and pictures and videos though out the day! Definitely will book against ten stars ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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15. 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
$45
per day

I can not say enough about Ebonee! She is totally amazing! She took such good care of Milo and sent pictures and videos of his stay with her. She is responsive and accommodating! I'm am more than pleased with her level of care.

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Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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16. Taylor L.

Loving Pet Sitter, Cats & Dogs
Kenwood, Chicago, IL, 60615
1.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$15
per day

About: I have years of experience caring for a variety of pets. This includes time spent pet sitting for puppies and kittens over the last 2 years. As I am a full-time grad student, I have a lot of free time throughout the week to dedicate to caring for my own pets along with others. I love to take the time to get to know pets for their personalities and preferences. Also will prioritize the needs and wants of owners above all else to ensure a safe and nurturing environment.

Sitter Profile Image: Talla A.
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Sitter Profile Image: Talla A.
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17. Talla A.

I love spoiling dogs
Douglas, Chicago, IL, 60616
1.4 mi. away
Boarding, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
7 repeat clients
from
$40
per day

Excellent communication and clearly responsible. My dog was happy to meet her when I went to leave her a second time. Would strongly recommend.

Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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18. 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
$45
per day

Kayla had great communication & Peppermint had a great time. Looking forward to booking again.

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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19. 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
$31
per day

Courtney is caring and nurturing to all pets. She’s cared for my pets since they were puppies and they love her! Courtney has helped so much with establishing the relationship with my pets to make them feel comfortable and loved.

Sitter Profile Image: Bridget E.
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Sitter Profile Image: Bridget E.
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20. Bridget E.

Pet loving home
Grand Boulevard, Chicago, IL, 60653
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
3 repeat clients
from
$50
per day

Bridget did an excellent job caring for our fur babies! She was responsive and sent adorable pictures through out the day. Our pups came home happy. We would definitely use her again!

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