Pet Sitting & Drop Ins in Woodlawn, 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

Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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1. Coretta S.

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

This is my second time using Coretta to watch my pets and she was just as amazing as the first. Her updates are so thorough, thoughtful, and sweet and can tell she genuinely enjoys caring for my animals.

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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2. Emily N.

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

Emily was so great with our cats! She always sent photo updates along with her check-in messages and she was flexible and able to come out again when the automatic feeder got jammed. I would definitely recommend Emily’s services and happily rebook her as a cat sitter!

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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3. Katherine B.

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

Katherine was great! Came in clutch for a last minute cat sitting request and provided really detailed updates and lots of photos/videos while I was away. I came home to a happy kitty and watered plants.

Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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4. 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
$10
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!

Sitter Profile Image: Nakeisha B.
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Sitter Profile Image: Nakeisha B.
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5. Nakeisha B.

Rover 101
Your fur baby will be in good hands
Grand Crossing, Chicago, IL, 60619
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
63 reviews
24 repeat clients
from
$20
per visit

Last month my hubby grandmother died and we had family over. A relative of mines was not pet friendly so we had Nakeisha sit for us. Prince was happy and we received texts with photos and videos. Clean apartment and very professional.

Sitter Profile Image: Dominique F.
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Sitter Profile Image: Dominique F.
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6. Dominique F.

Caring For Your Pet With Respect❤️
South Shore, Chicago, IL, 60637
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
35 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: Dominique C.
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Sitter Profile Image: Dominique C.
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7. Dominique C.

Lifelong Dog Lover and Caregiver!
Woodlawn, Chicago, IL, 60637
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 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.

Sitter Profile Image: Charles P.
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Sitter Profile Image: Charles P.
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8. Charles P.

Lover of 4 legged friends
Kenwood, Chicago, IL, 60615
2.1 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: Elizabeth H.
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Sitter Profile Image: Elizabeth H.
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9. Elizabeth H.

I already love your dog!
Woodlawn, Chicago, IL, 60637
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$17
per visit

Elizabeth is the best super responsive and very helpful she took great care of cat and sent me a picture everyday I definitely would recommend her! She even dropped my keys off for me 10/10

Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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10. 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
9 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.

Sitter Profile Image: Mayela E.
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Sitter Profile Image: Mayela E.
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11. Mayela E.

I’d like to be a dog in other lives
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$20
per visit

Stellar cat-sitter! Absolutely recommend, even for elderly cats with special needs :)

Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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12. John M.

UChicago student; animal lover
Hyde Park, Chicago, IL, 60637
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$20
per visit

John is excellent with both cats and dogs. He is incredibly patient and gentle with my cats who I have left in his care several times. John is also a big dog-lover and has cared for his three dogs for many years. John is reliable and dependable and will take excellent care of your pets!

Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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13. Emily L.

Love all pets 🫶
Hyde Park, Chicago, IL, 60637
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$20
per visit

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

Sitter Profile Image: Stephanie J.
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Sitter Profile Image: Stephanie J.
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14. Stephanie J.

They are special like we are!
South Shore, Chicago, IL, 60649
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$17
per visit

About: I have done volunteer work from Anti-Cruelty. I had to feed and walk the dogs. It was a great experience! I communicate well with pets. It fits very well. I plan to start part-time then go into full-time or whatever schedule is available first. Full or Part-time, based on availability. I make sure they are fed, walked, have exercise and activities, based on the breed and age of the pet. I will build connections also

Sitter Profile Image: Leah C.
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Sitter Profile Image: Leah C.
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15. Leah C.

Grad Student & Animal Lover
Hyde Park, Chicago, IL, 60637
0.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
3 repeat clients
from
$25
per visit

Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.

Sitter Profile Image: Carmen P.
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Sitter Profile Image: Carmen P.
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16. Carmen P.

A dog-less dog lover
Woodlawn, Chicago, IL, 60637
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
6 repeat clients
from
$30
per visit

Carmen was amazing to work with! Great communication and great with the cats.

Sitter Profile Image: Rebecca B.
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Sitter Profile Image: Rebecca B.
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17. Rebecca B.

Rover 101
Energetic and Focused Pet Care
Woodlawn, Chicago, IL, 60637
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
4 repeat clients
from
$25
per visit

Becca took exceptionally good care of our cat Autumn while my housemate and I were abroad. It had been hard to find good, reliable care (esp. due to some last minute travel plan changes on our part) but Becca stepped right in and everything went smoothly! Becca checked in everyday with updates and info and made sure to ask for tips to help Autumn adjust to having a relative stranger in the house. Thank you again for taking such good care of Autumn and giving is peace of mind while we were away!

Sitter Profile Image: Jack R.
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Sitter Profile Image: Jack R.
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18. Jack R.

dog walker and sitter
Woodlawn, Chicago, IL, 60637
0.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$17
per visit

Jack has taken the best care of my pug, Louis! He treats Louis with as much love and attention as I do and I can rest totally reassured that Louis is in the best hands when he’s with Jack. Jack also goes above and beyond, making sure that Louis runs around and gets plenty of exercise. He’s always super happy and worn out after hanging out with Jack :) As much as I’d love to think Louis is special, I’ve seen Jack extend that same special treatment to all the animals I’ve seen him care for. Any pet would be lucky to have Jack look after them - I can’t recommend him strongly enough!

Sitter Profile Image: Aolani "Catrina" C.
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Sitter Profile Image: Aolani "Catrina" C.
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19. Aolani "Catrina" C.

Unmatched Care for Your Pets
Hyde Park, Chicago, IL, 60637
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$22
per visit

This is my second time booking Catrina, and will continue to book with her! My dog is a little funny with new people, but she has been able to handle her very well and I can tell my pup is comfortable and happy. The communication is always fantastic, and my cat even loves to come out from hiding to get some pets and love. If the cat likes you, that’s a good sign.

Sitter Profile Image: Jessica S.
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Sitter Profile Image: Jessica S.
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20. Jessica S.

Passionate Pet Care Pro
Chicago, IL, 60649
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit

Jessica is simply the best when it comes to pet care! She's like a second mom to our furry family members. Always reliable and caring, Jessica goes out of her way to make sure our pets are happy and healthy. We couldn't ask for a better caregiver! Thanks, Jessica, for all you do!

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Woodlawn:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7915 owners have reviewed sitters in Woodlawn, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Rover.com is the simple, savvy way to find and book Woodlawn, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Woodlawn, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

Drop-In Visits