Pet Sitting & Drop Ins in Oakland, Chicago

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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1. Abi S.

Star Sitter
I’ll keep up with your pup!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
30 reviews
12 repeat clients
Profile image

Abi was the best! She is so caring and went above and beyond. When I asked her to check in with me a couple times while I was gone (8 days) she certainly did, and even sent photos which gave me peace of mind! I came home to very happy cats! I cannot recommend her enough. Thank you Abi!!

Availability updated 25 days ago
Sitter Profile Image: Niko F.
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Sitter Profile Image: Niko F.
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2. Niko F.

Star Sitter
Ensuring your pets safety/happiness
Lower West Side, Chicago, IL, 60616
3.2 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5.0 out of 5 stars
102 reviews
33 repeat clients
Profile image

Thank you so much for all the photos and updates! Baker was happy to have us home but with your care he was well looked after. If anyone is looking for a cat sitter I can highly recommend you as the affection and play time you give was well worth every penny. Thank you for taking care of our boy.

Availability updated today
Sitter Profile Image: Qutress T.
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Sitter Profile Image: Qutress T.
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3. Qutress T.

Star Sitter
a dog-person without dogs
Grand Boulevard, Chicago, IL, 60615
1.4 mi. away
Drop-In Visits
from
$17
per visit
5.0 out of 5 stars
60 reviews
18 repeat clients
Profile image

Qutress was so considerate, sweet, and caring with our kitty cat and we would absolutely love to book her again!! She did everything we needed to a T and sent us lots of helpful updates and cute photos too! We felt really happy and relieved as anxious pet parents knowing that Qutress was nearby and available to help with drop ins while we were out of town :)

Availability updated 4 days ago
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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4. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
148 reviews
42 repeat clients
Profile image

This past weekend was the first time Emily took care of my two cats and she was amazing. I left her a list of Kitty To Do’s and sticky notes all over the house lol and she knocked it all out at each visit. Unfortunately one of my cats is a super picky eater and you have to try a couple things for him to eat and she tried it all until he ate not once but twice then she would leave. She made my trip less stressful because I knew my boys where in good hands. She also is a great photographer, I received multiple pics of my boys at each visit which made my day!

Availability updated 16 days ago
Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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5. Danielle B.

Star Sitter
I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
1.5 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
29 reviews
5 repeat clients
Profile image

Danielle was amazing and truly went above and beyond when taking care of my three cats! Super fast communication, sent lots of pictures, and very thorough!! It was a relief to know they were in such great hands while we were away. Highly recommend!

Availability updated today
Sitter Profile Image: Ruslan S.
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Sitter Profile Image: Ruslan S.
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6. Ruslan S.

Taking Care of Your Pet as my own
Near South Side, Chicago, IL, 60616
1.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 reviews

Ruslan looked after our cat many times for a few days or longer. She is bald senior cat who eats special food and takes medications, and also doesn't like changes of scenery and requires a lot of attention and communication. So we were happy to turn to Ruslan, who put up with her quirks, provided care and warmth. She didn't seem to miss us at all, which is just right. We've always found it easy to communicate despite a bunch of requirements on our and the cat's side.

Availability updated 13 days ago
Sitter Profile Image: Katerina L.
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Sitter Profile Image: Katerina L.
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7. Katerina L.

Caring, detail oriented sitter!
Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
5.0 out of 5 stars
2 reviews
Profile image

Little Kaia took a liking to Katerina at first meeting which was a rarity since it takes a while for our corgi to open up to strangers. Katerina gave lots of pets and was patient with both senior pups. She also gave photos and updates. Looking forward to working with her again in the future.

Availability updated 16 days ago
Sitter Profile Image: Jordyn W.
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Sitter Profile Image: Jordyn W.
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8. Jordyn W.

Let’s make my dog jealous
Hyde Park, chicago, IL, 60615
1.7 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5.0 out of 5 stars
3 reviews

Jordyn would be an amazing dog sitter! I watched her raise her French bulldog Rae, from a puppy and he is so loving and playful. You can tell he has been treated with love and gets a lot of affection. She is patient and loves being around other dogs. Rae is bathed like a human and even gets his bottom wiped and cleaned after he poops😂. Jordyn would be great!

Availability updated 6 days ago
Sitter Profile Image: Andrea H.
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Sitter Profile Image: Andrea H.
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9. Andrea H.

Animal lover ❤️
Douglas, Chicago, IL, 60616
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
6 reviews

Andrea is the best, has her watch my dog Charming for a weekend. She followed all the instructions I left for her and also made sure that Charming took all his medication. She is an exceptional caretaker was very knowledgeable, reliable, efficient and devoted. She clearly has a love for animals and I will be using her again.

Availability updated today
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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10. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5.0 out of 5 stars
27 reviews
6 repeat clients
Profile image

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

Availability updated 4 days ago
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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11. Emily L.

Rover 101
Pet passionate care😊🫶
Chicago, IL, 60616
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
12 reviews
1 repeat client
Profile image

Emily was amazing. She was responsive, prompt, and so sweet. We will 100% be hiring her again to come check on our cat!!

Availability updated today
Sitter Profile Image: Alma G.
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Sitter Profile Image: Alma G.
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12. Alma G.

Caring, loving and responsible!
Chicago, IL, 60615
1.7 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$17
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients

About: My friends, family and neighbors have all counted on me to look after their pets since I was 15 years old. I grew up volunteering in dog shelters and caring for my own pet growing up. I treat all pets as if they were my own! I work full time at a fitness center, but my hours are flexible and I have Fridays and Saturdays off. I typically work later in the mornings and get off in the evenings, but I am able to adjust hours accordingly. I have a cozy apartment with a huge park and dog park 3 minutes away. I make my space work for them and really spend time with them outside and playing as much as they need. My neighborhood is great for those much needed walks!

Availability updated 4 days ago
Sitter Profile Image: Emma H.
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Sitter Profile Image: Emma H.
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13. Emma H.

Future Dr. Emma, DVM ☺️
Chicago, IL, 60615
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
42 reviews
13 repeat clients
Profile image

Emma is AMAZING!! She took such good care of our kitties, they warmed up to her so fast because they could sense her kind heart! Sent us lots of pics and kept us updated, and kept everything very tidy. So glad to have found her!

Availability updated 54 days ago
Sitter Profile Image: Madison C.
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Sitter Profile Image: Madison C.
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14. Madison C.

Big dog lover who's home full time!
Kenwood, Chicago, IL, 60653
0.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
1 review
1 repeat client

Madison has a love for all pets (Dogs especially!). She looks after our cats as if they were her own children and is very attentive to their needs...almost to the point of spoiling them. She's a really caring person.

Availability updated 56 days ago
Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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15. Kayla S.

✨Furry Earth Angels Wanted 🐈‍⬛🐕
Chicago, IL, 60615
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$22
per visit
5.0 out of 5 stars
31 reviews
16 repeat clients
Profile image

Kayla did a good job checking in on my cats while I was away. She refilled their water, changed their litter, cleaned up vomit, and played with them.

Availability updated 3 days ago
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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16. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients

Jabari is currently a co-owner of a 8-12 month old Yorkshire Terrier mix currently alongside me whom he frequently feeds, grooms and bonds with on a daily basis. Jabari has experience with both large and small breeds of dogs, he has worked with 1+ year old male Pure breed Cane Corso and 1+ year old female German Shepherd Mix who he has cared for and watched over several times over their life. As well as, already pet-sitting a variety of dogs for many owners within his own family. I would highly recommend Jabari for care for other's pets as he is responsible, caring and diligent about the well-being of all pets and properly caring for them according to their breeds, sizes and ages.

Availability updated 8 days ago
Sitter Profile Image: Maddison C.
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Sitter Profile Image: Maddison C.
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17. Maddison C.

I love dogs
Kenwood, Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
Profile image

Maddison took great care of Yettie and was super communicative, responsive, and prompt!

Availability updated 5 days ago
Sitter Profile Image: Samira C.
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Sitter Profile Image: Samira C.
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18. Samira C.

Full time teacher and animal lover
Chicago, IL, 60653
1.2 mi. away
Drop-In Visits, Dog Walking
from
$22
per visit
5.0 out of 5 stars
17 reviews
5 repeat clients
Profile image

Samira was very easy to work with on such short notice! She kept me updated and I felt I made the right choice by choosing her to do drop ins to check on my pup while I was out of town!

Availability updated 75 days ago
Sitter Profile Image: Valeria V.
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Sitter Profile Image: Valeria V.
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19. Valeria V.

Walk, play, cuddle and repeat!
Grand Boulevard, Chicago, IL, 60605
0.8 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
Profile image

Thanks for taking care of my Blue!

Availability updated 2 days ago
Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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20. Dee M.

Hyde Park Dog Lover
Grand Boulevard, Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client

Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I know she will get her exercise when she is with Dee. I cannot express enough how much I appreciate Dee & the genuine loving care she gives my little girl, Déjà. Highest recommendations from us!

Availability updated 35 days ago

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