Pet Sitting & Drop Ins in Roseland, 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
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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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1. Coretta S.

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

Coretta was great in every aspect! She was quick and thorough in her communications. She consistently sent pictures of her visits. And my cat Lewis loved being in her care. I will definitely book with Coretta again!

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Sitter Profile Image: Kathryn C.
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Sitter Profile Image: Kathryn C.
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2. Kathryn C.

Star Sitter
Hard-working and loving caregiver
Oak Lawn, IL, 60453
6.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
18 repeat clients
from
$15
per visit

Very attentive care for my timid cat. Followed all the care instructions very exactly and made sure to seek out my cat in hiding to confirm all was well. Recommended!

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Sitter Profile Image: Melissa B.
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Sitter Profile Image: Melissa B.
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3. Melissa B.

Star Sitter
I can't wait to meet your dog!
Morgan Park, Chicago, IL, 60655
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
11 repeat clients
from
$22
per visit

Melissa was super flexible and accommodating! She took such great care of my puppy & put my mind at ease by providing me updates during the check-in! She always had her own backup supplies just in case!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dominique C.
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Sitter Profile Image: Dominique C.
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4. Dominique C.

Lifelong Dog Lover and Caregiver!
Woodlawn, Chicago, IL, 60637
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$20
per visit

Dominique is excellent with Lily. She is patient, kind, and playful with her. She really goes the extra mile when working with my Lily. She is always on time and reliable. I highly recommend Dominique.

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Sitter Profile Image: Toni C.
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Sitter Profile Image: Toni C.
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5. Toni C.

Rover 101
Animal welfare enthusiast
Chicago, IL, 60655
3.6 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$17
per visit

Toni is great. Responsive, responsible, caring and capable. I felt very reassured after meeting her and knew I was leaving my cat in good hands. She kept me up to date on visits and I returned to a well cared for cat. The best!!

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Sitter Profile Image: Beverly B.
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Sitter Profile Image: Beverly B.
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6. Beverly B.

Star Sitter
Home full-time, individual care
Chatham, Chicago, IL, 60620
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
235 reviews
86 repeat clients
from
$22
per visit

Beverly was super helpful and kind with our dog Oliver. He immediately liked her and she was great at communicating and sending pictures/ updates. Will definitely be contacting her next time we need a pet sitter!

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Sitter Profile Image: Tonisa J.
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Sitter Profile Image: Tonisa J.
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7. Tonisa J.

Rover 101
Star Sitter
Your pups second home....
Calumet Heights, chicago, IL, 60617
2.9 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
69 reviews
31 repeat clients
from
$13
per visit

She is awesome with our doggy

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Sitter Profile Image: matt M.
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Sitter Profile Image: matt M.
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8. matt M.

Star Sitter
Dog lover with spacious backyard
Evergreen Park, IL, 60805
4.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
5 repeat clients
from
$17
per visit

Matt is an amazing compassionate human being. Has been a wonderful pet owner and has a great sense Knowing what a pet needs. Hire this guy. :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Darcelle M.
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Sitter Profile Image: Darcelle M.
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9. Darcelle M.

May be cat person But I'm also dog!
Pullman, Chicago, IL, 60628
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$15
per visit

Darcelle was great and my cats loved having her drop by to check on them. I appreciated that she played with them and cleaned up the food dishes. I recommend her and plan to call on her again when I can't be home.

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Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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10. Jasmine P.

Rover 101
Furry Friends' Paradise
Chicago, IL, 60438
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$15
per visit

Have great communication, very prompted and handles Molly with care as if molly was her own

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dominique F.
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Sitter Profile Image: Dominique F.
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11. Dominique F.

Caring For Your Pet With Respect❤️
South Shore, Chicago, IL, 60637
4.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
36 repeat clients
from
$20
per visit

Dominique did a wonderful job! She was the first sitter I hired for my new pet. Her videos and pictures of my little kitten made me feel a lot better about having to leave. I hope to employ Dominique many times in the future, she makes sure our fur babies are safe and loved.

Sitter Profile Image: Crystal A.
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Sitter Profile Image: Crystal A.
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12. Crystal A.

Oh! I wanna walk with somebody! 🥰
Washington Heights, Chicago, IL, 60643
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$20
per visit

I have one wire fox terrier and one boxer (he's 100 pounds) and crystal stayed with them an entire month and everyday I got pictures, updates, and so my babies having a GREAT TIME! Crystal also took care of my plants, house dusting, and brought in all my mail. It pained me when I moved from the city, because after six months I have not been able to find someone as good as Crystal. You can 100% trust her with your fur babies!!

Sitter Profile Image: Nariah B.
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Sitter Profile Image: Nariah B.
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13. Nariah B.

Fur Mama w/o chance of Fur Baby
Washington Heights, Chicago, IL, 60621
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
2 repeat clients
from
$20
per visit

Nariah was great! Took great care of my jazmine and even brought in a perishable package that was delivered and put it away for me. I mistakenly put the wrong address on my reservation and Nariah was understanding and still was able to help me out for the weekend. Will definitely use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tara P.
Sitter Profile Image: Tara P.

14. Tara P.

Loving, Happy, Safe, Fun Pet care
Morgan Park, chicago, IL, 60643
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
4 repeat clients
from
$25
per visit

Tara is great with dogs! She is very caring towards animals of all kinds. She always has the dogs best interest at heart. On warmer days she walks the dogs with a water bottle at the ready to keep them cool and refreshed. She is always willing to share treats with them and keeps them handy. She treats all dogs as if they were her own and is willing to give them the attention they need. Your dog will like her instantly.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Cheyenne D.
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Sitter Profile Image: Cheyenne D.
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15. Cheyenne D.

Dog mom! Let me love your babies!
Chicago, IL, 60617
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
4 repeat clients
from
$20
per visit

About: I have been a dog owner since childhood and have experience working with dogs of all ages and sizes. I am currently Mom to a Boxer Dane mix; as such, any boarding MUST have a meet-up first to ensure there is no hostility. My oldest dog is nearing 7 or 8, and I am familiar with diet-sensitive and senior dogs. I am currently unemployed - as such, I can accommodate most requests! I love all breeds of dog, and have no real preferences! I am willing to house sit, as well as care for other animals (cats, etc). Non-local requests will be accepted on a case by case basis (as I rely on public transit). I am looking forward to loving on your fur babies!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jayden Phoenix P.
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Sitter Profile Image: Jayden Phoenix P.
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16. Jayden Phoenix P.

Dogs are a humans bestfriend.
Roseland, Chicago, IL, 60628
0.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$25
per visit

Roxy was responsive, arrived as scheduled, and checked on our pets as requested. I also appreciate Roxy bringing in our mail packages that were left at the door. Thank you!

Sitter Profile Image: Shantell B.
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Sitter Profile Image: Shantell B.
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17. Shantell B.

I love pets & pets love me.
South Deering, Chicago, IL, 60617
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$19
per visit

Shantell does a great job taking care of my fur baby. He feels comfortable around her and responds well.

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Sitter Profile Image: Kathryne G.
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Sitter Profile Image: Kathryne G.
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18. Kathryne G.

Responsible and caring dog owner!
Washington Heights, Chicago, IL, 60643
1.4 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
3 reviews
from
$20
per visit

Kathryne is great with dogs! She is very patient and caring an you can tell how much she loves dogs by how she cares for her dog, Bailey. She has always been very kind and sweet to my sometimes difficult dog Sophie, which I have always really appreciated. If you want a sitter who will treat your dog like family, then you should book with Kathryne.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Cane E.
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Sitter Profile Image: Cane E.
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19. Cane E.

Prior vet tech, now social worker!
Chatham, Chicago, IL, 60619
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$14
per visit

Cane accepted sitting our 2 dogs and 4 cats at short notice. He provided pictures and plenty of updates while we were away and did well with my reactive dog. I was especially worried about leaving my dog with anyone and almost didn't go on the trip at all because of that but Cane did well meeting him outside and then was able to interact with him while we were gone! He continued to provide care for our pets even after losing access to his car due to the icy roads while we were away. It was very helpful to have someone with experience and patience to work with all our social animals. We will definitely reach out to him again next year 😄

Sitter Profile Image: Ellen M.
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Sitter Profile Image: Ellen M.
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20. Ellen M.

Rover 101
I'll run with you dog!
Beverly, Chicago, IL, 60643
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
19 repeat clients
from
$25
per visit

I was very pleased with Ellen’s care of my dogs. I would 100% recommend her and would definitely use her again. My dogs were well taken care of while I was gone!

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As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Roseland pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Roseland, Chicago who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

Drop-In Visits