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
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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
1.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
59 reviews
21 repeat clients
from
$17
per visit

Coretta was an amazing caretaker. She was consistent, on time, gave me thorough updates, and provided great care for my pets. 15 out of 10 would recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dominique C.
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Sitter Profile Image: Dominique C.
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2. 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
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.

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

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
3.5 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

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Sitter Profile Image: Beverly B.
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Sitter Profile Image: Beverly B.
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4. Beverly B.

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

Beverly did a fantastic job taking care of our cat! She was attentive with pictures and messages on each visit. She even double checked with us about the cat's food routine to be sure she was giving him enough. Lovely experience with a lovely person!!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Haley B.
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Sitter Profile Image: Haley B.
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5. Haley B.

🐈‍⬛ Cat Whisperer in Hyde Park! 🐈
Hyde Park, Chicago, IL, 60637
1.2 mi. away
Drop-In Visits
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$21
per visit

Haley was absolutely wonderful and took such great care of our cats while we were out of town. One of our cats requires medicine twice a day and she handled everything so well. Would definitely recommend her!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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6. Katherine B.

Star Sitter
🐶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
56 reviews
16 repeat clients
from
$20
per visit

Katherine was so helpful and responsible! She helped out with small tasks like picking up the mail and made sure my cat was taken care of even when she was feeling unwell. I'm sure any pet will have a good time with Katherine.

Sitter Profile Image: Elizabeth H.
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Sitter Profile Image: Elizabeth H.
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7. 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

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Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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8. 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
5 reviews
1 repeat client
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: Aolani "Catrina" C.
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Sitter Profile Image: Aolani "Catrina" C.
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9. Aolani "Catrina" C.

Star Sitter
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

Wonderful communication and reports, my cat and dog were both well taken care of! My little dog is a bit of an odd case so it was very nice having someone my dog warmed up to.

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
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: Nakeisha B.
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Sitter Profile Image: Nakeisha B.
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11. 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

Ms Barber have not watched my pets per say, but I have watched her care for her own pets with the up most love and respect more than anyone I have ever seen. She adhere’s to waste laws and she’s sensitive to aging animals as well. I say she’s a top notch animal lover and care taker.

Sitter Profile Image: Grace T.
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Sitter Profile Image: Grace T.
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12. Grace T.

Full time student & pet lover!
Woodlawn, Chicago, IL, 60637
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$17
per visit

Grace is an exceptional pet caregiver whom I recommend to anyone seeking a responsible and loving care for their furry friends. Grace has a unique ability to create a connection with any pet. I witnessed Grace's care firsthand when she helped me pet-sit a friend's cat. Not only did she ensure the cat's basic needs were met, but she also made time to play with the cat and give her lots of attention. Grace's responsible nature and genuine love for animals make her a great choice for anyone in need of a trustworthy pet caregiver.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jessica S.
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Sitter Profile Image: Jessica S.
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13. Jessica S.

Passionate Pet Care Pro
Chicago, IL, 60649
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
3 reviews
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!

Sitter Profile Image: Leah C.
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Sitter Profile Image: Leah C.
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14. Leah C.

Star Sitter
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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dominique F.
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Sitter Profile Image: Dominique F.
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15. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jumie T.
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Sitter Profile Image: Jumie T.
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16. Jumie T.

Dogs love me!
Chicago, IL, 60649
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$20
per visit

About: I am an artist and former dog owner with experience working as a private dog sitter since high school. I love pets immensely, and am so excited to meet yours! Every dog I get to greet is a gift, and I treat them as such. Through my own experience as a dog owner, and diverse experience with other dogs, I have learned a lot that I get to bring to these new situations. I know how vital calmness can be, and keep myself patient. I know every dog is different, so please share everything you can about your animal and all their quirks! Getting to interact with animals is so much fun and so fulfilling, I wish to spend more of my time doing it when I can. I currently work from home, so my schedule is incredibly flexible! I'm available for walks throughout the week and can stay with your fur baby as need be. I like to keep the care of your pet as close as possible to their normal routine, so please keep that information clearly written out if possible, or we can talk through it together.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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17. 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!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Carmen P.
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Sitter Profile Image: Carmen P.
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18. Carmen P.

Star Sitter
A dog-less dog lover
Woodlawn, Chicago, IL, 60637
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 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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19. 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

Rebecca was fantastic with our cat, Theo! We're new to the area so it was such a big comfort to know he was being well taken care of while we were out of town. Rebecca was intentional about following his quirky routines, sent us lots of pictures and videos, and made sure to check in even about the little things. We will definitely be reaching out to her again! :)

Sitter Profile Image: Jack R.
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Sitter Profile Image: Jack R.
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20. 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!

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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