Pet Setting & 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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Nick

DOGS ARE LIFE

Loop, Chicago, IL, 60607

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

"Nick is a very responsible adult. Growing up we always had dogs and always treated them very well. He also loves them a lot and will be a great dog worker de... (more)"

2. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

3. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

Confirmed Holiday Availability
4. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

Confirmed Holiday Availability
5. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

Drop-In Visits, Dog Walking

1 repeat client

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

6. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've cared for dogs since I could walk! I have experience both with my own dogs and with dogs that aren't as familiar with me, through volunteering... (more)

Confirmed Holiday Availability
7. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

About: I moved to Chicago from Gainesville, FL to get a fresh perspective and a change of pace. I'm an artist who spends most of my time making comics and... (more)

8. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"My dogs love and adore LeAnna! As soon as they see her, they jump, slobber and stick to her like glue. She babysat my pups for a week, I totally trusted he... (more)"

Confirmed Holiday Availability
9. Myk'La

Energetic, artsy, happy and caring

Chatham, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

Confirmed Holiday Availability
10. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have 14 years experience with a variety of animals, including exotics. I have taken care of animals with special needs and medications. While i... (more)

11. Jordan

Dog Lover and Rescuer

Calumet Heights, Chicago, IL, 60617

House Sitting, Drop-In Visits, Dog Walking

"Jordan is a kind, dedicated woman who gives her all to her passions. Her love of animals is enormous, as is her ability to care for them. She stands out by ... (more)"

12. Tyler Morgan

Energetic and very friendly.

Avalon Park, chicago, IL, 60619

Drop-In Visits, Dog Walking

"my sister tyler has always been a dog lover since she was a baby, I love that about her very emotional about dogs and especillay when it comes to animal crue... (more)"

13. Martineja

Fun, Comfort, and Love

Hyde Park, Chicago, IL, 60615

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

1 repeat client
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About: If you need a home away from home for your furry family member contact me today. My family is loving, kind, experienced with animals, and loves dog... (more)

14. Kelli

The Diva Dog Whisperer

Hyde Park, Chicago, IL, 60637

Drop-In Visits

"Kelli is amazing! She truly cares for dogs and I can tell that my puppies love her. She is always a pro - on time, treats in her pocket and ready for some fu... (more)"

Confirmed Holiday Availability
15. Lynettra

Experienced pet care provider

Kenwood, Chicago, IL, 60653

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

2 repeat clients

About: Hi, I'm Lyn. I am a pet care professional and an animal lover. I have a passion for pet care and have been in the field 5+ years. With my passion, ... (more)

16. Haley

Meet Your Dog's New Best Friend!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Haley is a warm and loving animal sitter. Not only will your animal be happy, but so will your home. She is extremely responsible and shows up when she say... (more)"

17. Brooke

Dog Loving Medical Student

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Brooke is a dog lover and would love to have a dog of her own, but because med school takes so much of her time, she has to wait. She misses all the love she... (more)"

18. Grace

Excited to meet your pup!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Gracie is stellar. I own two dogs, Vito and Thurston, and a large Tegu Lizard. Each needs walking, feeding, and love. Gracie, beyond being a sweetheart, i... (more)"

19. Catalina

Catalina, Dog Lover

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Catalina has always had a special relationship with dogs. When she was growing up, at various times, she had labradors, neapolitan mastiffs, rottweilers and ... (more)"

20. Keeshina

PETS ARE HUMANS IN DIFF.FORMS ÔŁĄTHEM

Grand Crossing, Chicago, IL, 60619

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

About: Hi , My name is Keeshina As a kid Me & my sisters Loves any pet we come in contact with!! My sis has 2 pits 2 cats ...my other a Lil tea cup! I ha... (more)

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Learn About Premier

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: