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.

Calendar Recently Updated
1. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Jennifer was great! She was super responsive, sent photos to keep us updated, and was able to do two extra visits on short notice. Thanks so much, Jennifer! (more)"

Confirmed availability
Labor Day
2. Masheika Verified Background CheckRoverGORover 101

Pupper pamperer :3

Kenwood, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"I have know. Masheika for 10 years. Her love and compassion for animals is unmatched. Dogs find their favorite aunt when Masheika is on the job. (more)"

Confirmed availability
Labor Day
3. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"I was referred to Elizabeth by Jax’s Doberman BFF, Tyson—his mom raved about the quality of care her dog received while she was away for business. I am very ... (more)"

Calendar Recently Updated
4. Joycee Verified Background Check

Dog care you can rely on.

Kenwood, Chicago, IL, 60653

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Joycee is a dog Super Mom! She has a natural gift with animals & will treat your fur baby as her own. She is GREAT with training & teaching commands. Whethe... (more)"

Confirmed availability
This weekend
5. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Alicia was great! Our dog is very high energy and is a bit difficult to walk but Alicia handled him great! Would definitely book with her again! (more)"

Calendar Recently Updated
6. Ariadne Verified Background Check

An assiduous, punctual dog-lover!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Ariadne is an amazing person who has always been great with dogs – she loves animals in general, and dogs in particular. She grew up with dogs and has helped... (more)"

7. Samone Verified Background Check

I went to school for this! :)

South Shore, Chicago, IL, 60649

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Wow, highly impressed with Samone from start to finish. She did check-ins on my cats while we were out of town. She did amazing job down to locating one of m... (more)"

Calendar Recently Updated
8. Kristina Verified Enhanced Background Check

Life is more fun with furry friends

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Kristina was a great cat-sitter. This is the first time we've come home from a trip that they haven't been annoyed with us. She sent lots of pictures. It was... (more)"

Calendar Recently Updated
9. Rita Verified Background Check

Reliable Chicago Dog Sitter!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hello! My name is Rita and I recently moved to Chicago after I graduated in December 2018 with Supply Chain Management. I'm 25 years old and I have... (more)

Calendar Recently Updated
10. Lauren Verified Background Check

Pug lover looking for doggy love!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Lauren is an animal lover who is also equally organized and detail oriented making sure my pets received the correct food, treats, and medication. One of my ... (more)"

Confirmed availability
Labor Day
11. Heather Verified Background Check

Room to grow and ways to explore

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: As a former dog owner and as a pet sitter for friends,I have a good understanding of what a pet requires when they are away from their owners and e... (more)

12. Alyse Verified Background Check

Caring and compassionate pet sitter

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Alyse is a responsible person who likes to help people. She’s had dogs and currently has a cat whom she cares for. Hasn’t taken care of anyone else’s pets ye... (more)"

13. Andrea Verified Background CheckRover 101

Fun times waiting to be had!

Washington Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Andy did a fantastic job befriending my demanding rescue kitty who doesn’t automatically understand people are his friends. Yet while I was away, Andy patien... (more)"

Calendar Recently Updated
14. Ashley Verified Background Check

Warm and friendly runs/walks, care

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

About: My best buddy is a golden retriever named Khloe. She's the light of my life, but since I'm in college, I have no where to put all of my pet-loving ... (more)

Calendar Recently Updated
15. Lynn Verified Background Check

Doggie Lover

South Shore, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Lynnie combines kindness and energy into one competent, hard-working individual. Were I to list her virtues, I could add intelligence, grace, responsible -- ... (more)"

Calendar Recently Updated
16. Cynthia Verified Enhanced Background Check

I've loved dogs & cats all my life!

South Shore, Chicago, IL, 60649

Drop-In Visits, Dog Walking

"Cynthia is a true dog lover. She's also a great mom, wonderful wife and compassionate professional. She has owned many dogs over the years, most recently her... (more)"

17. Nick Verified Enhanced Background Check

Pup up the Party w/ Nick!

South Shore, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

About: As a pet-care professional I take this job and responsibility extremely serious. One of the greatest things I could’ve ever inherited from my famil... (more)

Confirmed availability
Labor Day
18. John Verified Background Check

Cozy Studio Next to a Dog Park

Hyde Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"John has always been a dog lover! He is extremely responsible and will take care of your dog as if they were his own. There is no one better to trust with yo... (more)"

Calendar Recently Updated
19. Minhyo Verified Background Check

Flexible, caring, and active!

Hyde Park, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Testimonial from Rover user (since March 2019) Minhyo is my partner's little sister, and has watched our now 5-month mini goldendoodle on several occasion... (more)"

Confirmed availability
Labor Day
20. Jill Verified Background Check

I'll run with your dog

Hyde Park, Chicago, IL, 60637

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Jill loves all kinds of dogs. She has a 10 month shiba inu puppy, called Paper, and treats him like her own baby. She walks her regularly, feed him with high... (more)"

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 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.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Woodlawn, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including: