Pet Sitting & Drop Ins in Oakland, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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: Crystal R.
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Sitter Profile Image: Crystal R.
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1. Crystal R.

My home is where your pet is.
Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
89 reviews
39 repeat clients
from
$21
per visit

She was very flexible with our schedule and when we asked her if she could extend she had no issue whatsoever with it. She gave us constant updates and communication and when my dog ripped open a bag she let us know and took it out. I would highly recommend Crystal to anyone.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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2. Coretta S.

Loves to accommodate furry friends
South Shore, Chicago, IL, 60649
4.6 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
55 reviews
19 repeat clients
from
$17
per visit

Coretta is great! Appreciated the care she showed my cats, as well as her updates while I was traveling. Felt so much better leaving the country knowing they were being cared for so well.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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3. David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
79 reviews
32 repeat clients
from
$25
per visit

David was absolutely wonderful. Went above and beyond any rover sitter we have worked with, who were also great! He was incredibly kind and considerate with our pet and with our home. We highly highly recommend David for any of your pet’s needs!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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4. Michael D.

Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
4.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
8 repeat clients
from
$20
per visit

Michael was easy to work with and it really seems like he enjoys spending time with animals. Any pet would be in good hands with him. Will definitely be in touch with him again!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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5. Emily N.

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

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!

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Sitter Profile Image: Sidoni G.
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Sitter Profile Image: Sidoni G.
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6. Sidoni G.

Happy human for happy pups!
Lower West Side, Chicago, IL, 60608
4.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per visit

About: I have over 10 years experience caring for mainly dogs and cats. I’ve cared for pets of all ages and needs, starting with puppies and have had the honor of supporting multiple pets with end of life needs as well. I am a freelance designer that has a flexible schedule and am available starting at 7:30am through early afternoon 1pm. Monday through Friday and open to weekends if needed. I have a car and at home have access to an enclosed patio where pets are free to run around out energy running around and practice daily games and training exercises.

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Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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7. 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
$12
per visit

Taylor went above and beyond, she was super kind and understanding of our dogs needs. She provided lots of updates and we felt assured that our pets were in safe hands!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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8. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$23
per visit

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

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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9. Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
16 repeat clients
from
$20
per visit

KT was the best with our two kitties! They gave great photo/video updates and communicated with me about any questions/issues that arose. They had a calm presence and the cats seemed to like them immediately. Will definitely book KT again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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10. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$18
per visit

I highly recommend Chijioke for pet sitting. They are so reliable and caring!! I have booked them multiple times to pet sit for me while I've been out of town and they do a fantastic job every time! They cleaned the litter, fed and kept my cat company. Chijioke is a great communicator, they are thorough and easy to talk to! Plus they kept me updated throughout! A superstar pet sitter! Highly recommend 10/10!

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Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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11. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$22
per visit

Sujae is an excellent cat sitter. She came for drop in visits on time and consistently over multiple days. I liked seeing pictures of all the cats and the nice notes she left. She helped me out of a jam when another sitter cancelled my pet sitting while I was already out of town. Rover helped me find Sujae and I’m super happy we found each other! Sujae did a wonderful job for me and my cats. Thanks Sujae!

Sitter Profile Image: Addy T.
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Sitter Profile Image: Addy T.
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12. Addy T.

Experienced with cats and dogs!
Chicago, IL, 60616
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$15
per visit

Addy was awesome!!! Thank you so much!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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13. Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60616
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
86 repeat clients
from
$30
per visit

Dailia is fantastic. She watched our cat for us while we were gone and did an amazing job. Great communication and our cat even liked her and she likes nobody.

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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14. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$17
per visit

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!!

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Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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15. Madeleine G.

Dog lover/babysitter for your pup!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
10 repeat clients
from
$16
per visit

Madeleine was great with our dog and was flexible enough to work with our changing schedules. Our dog is used to having someone around all day, so she greatly appreciated the time Madeleine spent with her.

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Sitter Profile Image: Andres R.
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Sitter Profile Image: Andres R.
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16. Andres R.

I care for your pets as my own!
Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
2 repeat clients
from
$16
per visit

Andres was incredible with our dog. We had not left her alone with a dog walker before and we couldn’t have been happier. The pictures of our dog also show us how happy she was.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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17. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$16
per visit

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.

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Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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18. Jasmine P.

Rover 101
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
61 reviews
21 repeat clients
from
$30
per visit

Jasmine was wonderful! We had just adopted our new kitty Ollie and he badly needed his claws trimmed. We didn't want to traumatize him with a vet trip so soon after we'd brought him home, so we asked Jasmine if she could come and show us how to trim his nails at home since neither of us was familiar with the process. She went above and beyond both trimming his longest claws and giving us lots of helpful tips to help us succeed with the process ourselves. Highly recommend Jasmine to care for your feline friends!

Sitter Profile Image: Charles P.
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Sitter Profile Image: Charles P.
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19. Charles P.

Lover of 4 legged friends
Kenwood, Chicago, IL, 60615
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit

Charles is one of the most caring people that someone could entrust their pet with. In addition to the dedication that he shows to his own pet, he has the utmost respect for all creatures even down to the smallest insect. He is very attentive and detail-oriented, especially as it relates to the needs or wants of animals. Finally, he is dependable and would be an excellent steward for anyone's pets.

Sitter Profile Image: Katie T.
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Sitter Profile Image: Katie T.
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20. Katie T.

🦮Chihuahua to Mastiff, big & small
Chicago, IL, 60653
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$20
per visit

Katie is the best! She took exceptional care of my cat while I was away on a trip last winter. She stopped by my apartment frequently to fill up the food bowl, water bowl, and take the litter out, providing me regular updates on Klo (my cat) as she did so. Katie even went above and beyond and was happy to fulfill an extra request I had for her which was to spend some extra time with Klo, who is a bit anxious, to make sure that she was comfortable and had some company for a few hours a day while I was gone. Klo and I couldn't be happier with Katie's help!

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Dog lovers in Oakland, Chicago, IL love pet sitters on Rover.com. Over 7915 pet owners have reviewed pet sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Chicago can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakland, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Oakland, Chicago who can provide the care your pet needs, when they need it.

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