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

Confirmed availability: Easter Weekend
Sitter Profile Image: Coretta S.
Verified Enhanced Background Check
Sitter Profile Image: Coretta S.
Verified Enhanced Background Check

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
46 reviews
16 repeat clients
from
$17
per visit

We highly recommend Coretta! She was very deliberate with each step in getting to know our expectations and in meeting our cat. Our cat is very active and gets lonely when we’re not home, but we had nothing to worry about because Coretta made him so happy:) She gave us updates and sent pictures from every visit. We will definitely seek her services next time we need a cat sitter!

Calendar Recently Updated
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check

2. 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
54 reviews
15 repeat clients
from
$20
per visit

Katherine is wonderful! We have a new kitten and an older fella cat, we had to leave town for a week, and weren't sure how the kitten would respond to his first time with us being away, how many things would be broken, and who could be a good fit to keep an eye on things and make sure the boys were well cared for. Katherine is an excellent communicator, provides tons of great information during visits, and gave us peace of mind that our home and kitties were in good hands. If Katherine is available, you'll be lucky to have them!

Confirmed availability: Easter Weekend
Sitter Profile Image: Aolani "Catrina" C.
Verified Enhanced Background Check
Sitter Profile Image: Aolani "Catrina" C.
Verified Enhanced Background Check

3. 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
12 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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Jasmine P.
Verified Background Check
Sitter Profile Image: Jasmine P.
Verified Background Check

4. Jasmine P.

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

Jasmine really put me at ease with dropping in on my new doggo, Bingsoo. She was kind and caring and knowledgeable. She was attentive to special needs and a great communicator. Dog whisperer forreal!

Calendar Recently Updated
Sitter Profile Image: Stephanie J.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie J.
Verified Enhanced Background Check

5. 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

Calendar Recently Updated
Sitter Profile Image: Nycol H.
Verified Enhanced Background Check
Sitter Profile Image: Nycol H.
Verified Enhanced Background Check

6. Nycol H.

Hi, I’m Nycol!
Hyde Park, Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits
from
$25
per visit

Nycol is incredibly responsible and caring towards both animals and humans! Nycol has watched over our dear Sadie and Bernie for the last 2 years and she is still the only one we trust to watch them! I’m immensely grateful for Nycol and the bond she shares with our loving fur babies.

Calendar Recently Updated
Sitter Profile Image: Olivia A.
Verified Enhanced Background Check
Sitter Profile Image: Olivia A.
Verified Enhanced Background Check

7. Olivia A.

Flexible and reliable pet sitter!
Chicago, IL, 60615
1.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$17
per visit

Olivia did a great job checking in on both my cat and my dog. Both the cat and the dog are shy and usually take a while to warm up to new people, but they both seemed to love Olivia. She was also very communicative and sent a great pic of my guys. Highly recommend, ill definitely be rebooking next time I need a drop in.

Confirmed availability: Easter Weekend
Sitter Profile Image: Leah C.
Verified Enhanced Background Check
Sitter Profile Image: Leah C.
Verified Enhanced Background Check

8. 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: Shakira C.
Verified Background Check
Sitter Profile Image: Shakira C.
Verified Background Check

9. Shakira C.

RoverGO
Rover 101
Your Pup is My Pup
South Shore, Chicago, IL, 60649
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
7 repeat clients
from
$34
per visit

So professional and kind! Great communication!

Confirmed availability: Easter Weekend
Sitter Profile Image: Nephritia H.
Verified Enhanced Background Check
Sitter Profile Image: Nephritia H.
Verified Enhanced Background Check

10. Nephritia H.

Hey there
Englewood, Chicago, IL, 60621
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
23 years of experience
from
$16
per visit

About: I'm a student who loves animals ESP dogs. I've always been around or had a dogs up even now. I own a very playful pit bull so I can handle big dogs with energy. So if you leave ya dog in my hands u can trust that he/she will be taken care of. I'll care for your dog as if he/she were my own. I am flexible with time and cancellations. If I do dog stop bys I willl make sure your pet is well taken care of while ur away even if it is not just your dog. If u have other animals I can make sure while your away that they have what they need as well. I'm an animal lover. Thank you Working part time at a pet store; also in a part time student. so I have lots of time to tend to any fur babies even my own. I crate train my pets but they are all well trained to be around other pets and people. I have multiple crate if needed. O

Confirmed availability: Easter Weekend
Sitter Profile Image: Carmen P.
Verified Enhanced Background Check
Sitter Profile Image: Carmen P.
Verified Enhanced Background Check

11. 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
6 reviews
4 repeat clients
from
$30
per visit

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

Confirmed availability: Easter Weekend
Sitter Profile Image: Emily L.
Verified Enhanced Background Check
Sitter Profile Image: Emily L.
Verified Enhanced Background Check

12. 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: Easter Weekend
Sitter Profile Image: Shanice H.
Verified Enhanced Background Check
Sitter Profile Image: Shanice H.
Verified Enhanced Background Check

13. Shanice H.

The best walk for your best friend!
Woodlawn, Chicago, IL, 60637
0.4 mi. away
Drop-In Visits, Dog Walking
5 years of experience
from
$25
per visit

About: I've taken care of dogs (big and small of different kinds) since I was 10. My family and neighbors have relied on me to walk, bathe, feed and play with their pets when needed. I've worked with both puppies and senior dogs, providing the care and attention they deserve. I'm an incoming freshman in college so I have plenty of time to care for your dogs! I am available Sunday through Wednesday from 8 am - 8 pm for dog sitting and dog walking. I do work part-time and can accommodate to a schedule that works well for us both. I am very mindful of fences as I watch your dog and will ensure the area is secure before they are let into the yard. Relating to walks, I will always ensure your dog is secure and that my attention is fully on them to ensure their safety. If there is anything I need to know about your dog and their health that will be vital to my service, please let me know!

Confirmed availability: Easter Weekend
Sitter Profile Image: Wade S.
Verified Enhanced Background Check
Sitter Profile Image: Wade S.
Verified Enhanced Background Check

14. Wade S.

The Dog Whisperer 🐾
South Shore, Chicago, IL, 60649
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
from
$25
per visit

Wade is reliable. He’s always on time and goes above and beyond for my Bear. We love him. He knows a lot about different dog breeds too and gives great tips for training. I’m definitely booking him.

Calendar Recently Updated
Sitter Profile Image: Jessica S.
Verified Background Check
Sitter Profile Image: Jessica S.
Verified Background Check

15. 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 beyond amazing, I met her walking my dog one night and from that moment I could tell how passionate she is about dogs. She’s super sweet and caring and Dino (my dog) loves her like nobody’s business!

Sitter Profile Image: Elizabeth H.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth H.
Verified Enhanced Background Check

16. 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 was great! She provided photos of Maize while I was on vacation including before they became best friends. My cat isn't around a lot of people but it was great to see by the second time she visited, Maize knew Elizabeth was friendly!

Confirmed availability: Easter Weekend
Sitter Profile Image: Jumie T.
Verified Enhanced Background Check
Sitter Profile Image: Jumie T.
Verified Enhanced Background Check

17. 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
1 review
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.

Sitter Profile Image: Jack R.
Verified Enhanced Background Check
Sitter Profile Image: Jack R.
Verified Enhanced Background Check

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!

Confirmed availability: Easter Weekend
Sitter Profile Image: Emma & Emily F.
Verified Enhanced Background Check
Sitter Profile Image: Emma & Emily F.
Verified Enhanced Background Check

19. Emma & Emily F.

We love making new furry friends!
Hyde Park, Chicago, IL, 60615
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$25
per visit

OMG! I'm so happy to have found Emma and Emily. They are the best team that I've worked with on Rover. Their attention to detail is superb. My cats were all a-glow when I returned home. I think they prefer Emma and Emily to me! They kept me informed of how things were going and I felt so comfortable being away, knowing they would be there to take care of my cats. I highly recommend them and you should have no hesitation when booking them! Thank you, Emma and Emily. Cheers, Marguerite

Sitter Profile Image: Abraham H.
Verified Enhanced Background Check
Sitter Profile Image: Abraham H.
Verified Enhanced Background Check

20. Abraham H.

Animal lover, experienced caregiver
Hyde Park, Chicago, IL, 60615
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$30
per visit

Abraham is an amazing caregiver and is a huge animal lover. He’s walked both of my dogs multiple times and they always come back exercises and happy. He has also sat for me and the pets love him. He is truly the best!

Search Map

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