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

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Yingyue L.
Verified Enhanced Background Check
Sitter Profile Image: Yingyue L.
Verified Enhanced Background Check

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
19 reviews
3 repeat clients
from
$46
per day

Yingyue was amazing with my little Bruno, very patient and caring. She kept me updated throughout the day helping me do what I needed to do knowing my baby was well. He came back happy and relaxed. Thank you !

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Morgan D.
Verified Enhanced Background Check
Sitter Profile Image: Morgan D.
Verified Enhanced Background Check

2. 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
17 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: E K.
Verified Background Check
Sitter Profile Image: E K.
Verified Background Check

3. 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 day

As always, Liz and her family did a great job with my little pup. He’s always tuckered out when he gets home and she sends me updates throughout the day as to what he’s up to. I can’t recommend her enough for a dog sitter!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashley M.
Verified Enhanced Background Check
Sitter Profile Image: Ashley M.
Verified Enhanced Background Check

4. 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
$38
per day

Ashley was absolutely amazing! She went above and beyond to make sure that my dog was comfortable with his stay at her house while I worked. She was very communicative, made sure to have full understanding of his care, and gave him lots of love! From the moment I dropped him off, I can tell she really cares about the pets she and her daughter care for, when I picked Echo up at the end of the day, he was so sad to leave! I’ll definitely be booking with Ashley again! :)

Sitter Profile Image: Ashley B.
Verified Background Check
Sitter Profile Image: Ashley B.
Verified Background Check

5. 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
74 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.

Calendar Recently Updated
Sitter Profile Image: Lisa H.
Verified Enhanced Background Check
Sitter Profile Image: Lisa H.
Verified Enhanced Background Check

6. 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
$48
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

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: David R.
Verified Enhanced Background Check
Sitter Profile Image: David R.
Verified Enhanced Background Check

7. 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
158 reviews
50 repeat clients
from
$57
per day

This is the first time our 6 months old puppy stayed at a sitter and we couldn’t be happier with David! He’s very communicative and we got a lot of pictures and updates through out the day. Ginkgo came home very happy and all tired out! Glad she got to meet David’s dogs and learned how to socialize. Highly recommend!

Calendar Recently Updated
Sitter Profile Image: Jamie & Ritz W.
Verified Enhanced Background Check
Sitter Profile Image: Jamie & Ritz W.
Verified Enhanced Background Check

8. 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!

Sitter Profile Image: Coraihma S.
Verified Enhanced Background Check
Sitter Profile Image: Coraihma S.
Verified Enhanced Background Check

9. 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
6 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

Sitter Profile Image: Vick D.
Verified Background Check
Sitter Profile Image: Vick D.
Verified Background Check

10. 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!

Calendar Recently Updated
Sitter Profile Image: Jillian K.
Verified Enhanced Background Check
Sitter Profile Image: Jillian K.
Verified Enhanced Background Check

11. Jillian K.

NP student, RN, & doodle mom
Near South Side, Chicago, IL, 60605
3.1 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$40
per day

Jillian is a superb pet caregiver, she has taken care of my energetic and sometimes overwhelming staffy mix. She handles him with ease and grace. She is such a caring pet lover, always attentive and caring. Jill will go above and beyond to care for you pet, treating it with love like it is her own. Jill is a wonderful pet caregiver, when Jill is watching my own dog I know he is in great hands.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Makeba L.
Verified Enhanced Background Check
Sitter Profile Image: Makeba L.
Verified Enhanced Background Check

12. 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.

Calendar Recently Updated
Sitter Profile Image: Katie "Anni" W.
Verified Enhanced Background Check
Sitter Profile Image: Katie "Anni" W.
Verified Enhanced Background Check

13. Katie "Anni" W.

Welcoming all fur babies :)
Near South Side, Chicago, IL, 60616
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$40
per day

I have booked her multiple times for my dogs when I go on vacation and business trips. She always makes them feel comfortable right away and I can tell they are having a good time when I see their pictures together. I would recommend her to anyone trying out Rover!

Calendar Recently Updated
Sitter Profile Image: Nicole K.
Verified Enhanced Background Check
Sitter Profile Image: Nicole K.
Verified Enhanced Background Check

14. Nicole K.

Pet Loving College Student
Bridgeport, Chicago, IL, 60609
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$33
per day

Nicole has been great with my reactive dog! She’s super communicative and timely with walking Pi and Pi looks forward to having her come around. Pi is a 3 legged dog who is dog reactive, so it’s not always easy to find someone who can accommodate her needs, but I can count on Nicole to do just that.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: MariaJose R.
Verified Enhanced Background Check
Sitter Profile Image: MariaJose R.
Verified Enhanced Background Check

15. 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
$30
per day

MariaJose loves dogs and it shows. She is very careful with following owner’s instructions. My dog Princesa is delicate and tempermental but she took care of her so well! She’s my go-to whenever I’m out of town or need an extra hand

Sitter Profile Image: Willy J.
Verified Enhanced Background Check
Sitter Profile Image: Willy J.
Verified Enhanced Background Check

16. 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
16 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: Kayla S.
Verified Enhanced Background Check
Sitter Profile Image: Kayla S.
Verified Enhanced Background Check

17. 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.

Sitter Profile Image: Chaeyeong J.
Verified Enhanced Background Check
Sitter Profile Image: Chaeyeong J.
Verified Enhanced Background Check

18. Chaeyeong J.

Reliable Rover for ur furry friends
Kenwood, Chicago, IL, 60615
1.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$40
per day

Chaeyeong was super accommodating and took pictures of my dogs during their stay so that I knew what my dogs were up to even though I was not with them.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Bridget E.
Verified Background Check
Sitter Profile Image: Bridget E.
Verified Background Check

19. 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!

Sitter Profile Image: Talla A.
Verified Enhanced Background Check
Sitter Profile Image: Talla A.
Verified Enhanced Background Check

20. 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.

Search Map

Doggy Day Care