Dog Boarding in Oakland, Chicago

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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
from
$45
per night
5.0 out of 5 stars
291 reviews
128 repeat clients
Profile image

Once again Charlie had a great stay with Liz! he is still tired from all the play he had. We always feel at ease when we travel knowing our dog is in good hands!

Availability updated 15 days ago
Sitter Profile Image: Tamara J.
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Sitter Profile Image: Tamara J.
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2. Tamara J.

Star Sitter
Experienced Dog Owner
Grand Boulevard, Chicago, IL, 60653
0.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$46
per night
5.0 out of 5 stars
14 reviews
6 repeat clients
Profile image

Was excellent leaving Milo in Tamara’s care; super responsive and flexible, sent regular updates, had a very clean home with super cute dogs. Would happily recommend and rebook.

Availability updated yesterday
Sitter Profile Image: Bola A.
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Sitter Profile Image: Bola A.
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3. Bola A.

Star Sitter
Big time dog lover 😄
Hyde Park, Chicago, IL, 60615
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$49
per night
5.0 out of 5 stars
89 reviews
24 repeat clients
Profile image

I have two small 8-year-old dogs. They spent 10 days with Bola. Bola was great, she clearly puts her heart into this job. She sent pictures every two or three days. The living room has a clean wooden floor. The small fenced grassy yard is perfect for small dogs to run and sniff around. Bola even delivered the dogs to my home at the end of their stay (a 15-minute drive). I warmly recommend her service.

Availability updated 22 days ago
Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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4. Ashley M.

Rover 101
Star Sitter
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$53
per night
5.0 out of 5 stars
90 reviews
27 repeat clients
Profile image

Ashley and her daughter treated our dog as if she was their own! Regular updates made me feel so confident that she was well taken care of. No issues with the other dogs she had in her care that weekend either. Will definitely book again!!

Availability updated today
Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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5. Kayla S.

Star Sitter
✨Furry Earth Angels Wanted 🐈‍⬛🐕
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$49
per night
5.0 out of 5 stars
45 reviews
21 repeat clients
Profile image

Kayla took great care of my pup and was super fast with responding to any questions I had and sent some cute pic updates which I love! Will for sure come to Kayla again!

Availability updated 6 days ago
Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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6. Kyle H.

Rover 101
Star Sitter
Almost 20 years of experience!
Hyde Park, Chicago, IL, 60615
1.9 mi. away
Boarding
from
$55
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
Profile image

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.

Availability updated 7 days ago
Sitter Profile Image: Emily S.
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Sitter Profile Image: Emily S.
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7. Emily S.

Star Sitter
WFH Pup Lover
Near West Side, Chicago, IL, 60607
4.4 mi. away
Boarding, Doggy Day Care
from
$45
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
Profile image

Emily was so wonderful with my 5 y/o lab mix! She was super easy to communicate with, and Frankie loved staying with her - she didn't want to leave. We'll definitely be asking Emily to watch Frankie again soon.

Availability updated 2 days ago
Sitter Profile Image: Ashley R.
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Sitter Profile Image: Ashley R.
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8. Ashley R.

WFH Cat lady❤️dog lover
Woodlawn, Chicago, IL, 60637
2.8 mi. away
Boarding, Doggy Day Care
from
$40
per night
5.0 out of 5 stars
5 reviews
Profile image

Ashley is the greatest!! I was a little worried about leaving my kitten Hadley for two weeks, but he immediately settled into her home and it was clear from the pictures and videos she sent of him always at her side and playing with her cat Pepsi that he adored both of them. Ashley sent me pictures and kept me updated every day, was so accommodating of my schedule and Hadley's routine, and gave him lots of attention. She was super easy to coordinate and communicate with, Hadley settled back in with me as though I’d never left, and I’ve already booked his next stay with her :)

Availability updated 4 days ago
Sitter Profile Image: Waverly J.
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Sitter Profile Image: Waverly J.
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9. Waverly J.

Your Fav Pet Sitter!
Grand Boulevard, Chicago, IL, 60653
1.1 mi. away
Boarding
from
$35
per night
5.0 out of 5 stars
106 reviews
59 repeat clients
Profile image

Waverly is very positive, and upbeat- the perfect ingredients for my high energy puppy. She has a big yard, which Zen loved playing in Noah and Shiloh. I would use her services again.

Availability updated 6 days ago
Sitter Profile Image: Anjana & Harsh N.
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Sitter Profile Image: Anjana & Harsh N.
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10. Anjana & Harsh N.

Star Sitter
Fetch-tastic Fun: Your Dog's Vacay!
Near West Side, Chicago, IL, 60607
4.6 mi. away
Boarding, Dog Walking
from
$50
per night
5.0 out of 5 stars
19 reviews
4 repeat clients
Profile image

Amazing as always! I’ve used them several times and my dog is always so excited to see them!! Great communication and they take amazing care of my dog.

Availability updated yesterday
Sitter Profile Image: Jennifer N.
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Sitter Profile Image: Jennifer N.
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11. Jennifer N.

Star Sitter
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
from
$49
per night
5.0 out of 5 stars
175 reviews
101 repeat clients
Profile image

Jennifer is great! Very convenient to book, even last minute. Fast response times and plenty of pictures and videos throughout the stay. Daisy always looks like she's having a great time. Highly recommend!

Availability updated today
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Katie "Anni" W.
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Sitter Profile Image: Katie "Anni" W.
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12. Katie "Anni" W.

Star Sitter
Need work from home companions!
Near South Side, Chicago, IL, 60616
2.7 mi. away
Boarding, House Sitting, Doggy Day Care
from
$50
per night
5.0 out of 5 stars
48 reviews
17 repeat clients
Profile image

Katie was absolutely awesome! She cared for my grumpy old man diabetic cat like he was her own. I was so thankful for all of her great updates and photos, it really put my mind at ease so I could enjoy my vacation. She had great communication, knowledge about pets, and is super genuine and caring. I would 100% recommend her to care for your pet(s).

Availability updated today
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Nicky V.
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Sitter Profile Image: Nicky V.
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13. Nicky V.

Star Sitter
Your Pet's New Best Friend!
Bridgeport, Chicago, IL, 60608
2.8 mi. away
Boarding, Doggy Day Care
from
$55
per night
5.0 out of 5 stars
24 reviews
6 repeat clients
Profile image

Nicki is the best. Hands down. Our new adopted Airedale has a lot of energy and is still timid with people. All the pictures and videos Nicki sent us during our trip showed that our dog was happy and playing the entire time. We cannot thank Nicki enough for welcoming us into her home with our fur baby. Thanks again Nicki!

Availability updated yesterday
Sitter Profile Image: Charlotte D.
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Sitter Profile Image: Charlotte D.
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14. Charlotte D.

Star Sitter
Recent grad who adores dogs!!
Near West Side, chicago, IL, 60661
5.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
68 reviews
15 repeat clients
Profile image

Charlotte, I loved, being able to count on you once again! I really like her and I always feel very comfortable when Lucy is with her. Thank you again, always for sending photos and messages. Thank you

Availability updated 12 days ago
Sitter Profile Image: Lisette S.
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Sitter Profile Image: Lisette S.
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15. Lisette S.

Star Sitter
For the love of pets!
McKinley Park, Chicago, IL, 60609
3.6 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$30
per night
5.0 out of 5 stars
28 reviews
4 repeat clients
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I can always count on lisette!

Availability updated 47 days ago
Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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16. Willy J.

Star Sitter
Reliable Dog Lover at your Service
Douglas, Chicago, IL, 60653
1.1 mi. away
Boarding, Doggy Day Care
from
$52
per night
5.0 out of 5 stars
20 reviews
7 repeat clients
Profile image

So appreciative of Willy and his wife taking care of our older dog for several nights! We were very comfortable while away knowing that he was in good hands.

Availability updated 6 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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17. Ann-Marie H.

Star Sitter
Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
2.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per night
5.0 out of 5 stars
21 reviews
7 repeat clients
Profile image

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.

Availability updated 39 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Dwight C.
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Sitter Profile Image: Dwight C.
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18. Dwight C.

Rover 101
Star Sitter
Work from home - large fenced yard
Woodlawn, Chicago, IL, 60637
3.4 mi. away
Boarding, Doggy Day Care
from
$30
per night
5.0 out of 5 stars
172 reviews
67 repeat clients
Profile image

Dwight was wonderful: responsive to questions, available for convenient drop off and pick up, and truly someone who cares for animals. Would recommend him hands-down!

Availability updated 14 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Denontae G.
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Sitter Profile Image: Denontae G.
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19. Denontae G.

Your Pet’s Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
3.6 mi. away
Boarding
from
$50
per night
5.0 out of 5 stars
3 reviews
Profile image

Denontae and his partner Holly have taken great care of our sweet boy probably a dozen different occasions now. It is comforting to know he is not only well cared for but has a great time while he stays with them. As always, thank y’all so much

Availability updated yesterday
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: DEMIN Z.
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Sitter Profile Image: DEMIN Z.
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20. DEMIN Z.

Rover 101
Univ.Staff &Tail Wagging Care
Near South Side, Chicago, IL, 60605
3.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
47 reviews
9 repeat clients
Profile image

Demin accepted a last minute request after original sitter canceled two days before stay. I’m so happy to have found her, she’s literally the best sitter yet for Honcho! She followed care instructions to a tee, provided daily reports and pics, and was very responsive. No walk was the same, she took him to the park, along the lake, to the beach, just to name a few places. This was daily during his stay! I could tell from the pics that he was comfortable and relaxed after fun filled days. Drop-off & Pick-up both were a breeze. I can’t say enough about Demin’s care for my dog. She is now my top choice to care for my dog while away.

Availability updated today
Confirmed availability for Presidents' Day Weekend

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