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.

Available this weekend
1. Jamey

Fun and compassionate caretaker!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Jamey is our favorite pet sitter because she showers our furbabies with love and attention while also taking care of their needs. Jamey is especially great w... (more)"

2. Krista

Flexible schedule, love dogs

Hyde Park, Chicago, IL, 60615

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

About: Other dog owners describe me as a caring, responsible, loving dog lover and pet sitter. I'm a current grad student so I have a flexible schedule to... (more)

3. Cosette

Forever dog-lover

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi there! I am a careful and attentive dog (and kid) sitter, with lots of love to give! I have owned and cared for dogs since a child and currently... (more)

Available this weekend
4. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Hello, Rover! Simone has cared for my pup, Honey on several occasions & I have never come home to an unhappy pet! She is kind and where Honey is concerned... (more)"

5. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Anne texted me each time she was there, even sending updates when our dog had an upset stomach. Thanks Anne for a great weekend of care for our dog!! (more)"

6. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

9 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)"

7. Thandaway

Pre-vet student majoring in cuddles

South Shore, Chicago, IL, 60649

Drop-In Visits, Dog Walking

"Thandaway is my daughter and she has been the owner and care taker of two dogs here at home. She has always loved animals and has decided to make veterinaria... (more)"

Available this weekend
8. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"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)"

9. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

About: Hello everyone! My name is Breana :). I am currently obtaining my Master's in Speech-Language Pathology. I am reliable, responsible and an animal l... (more)

10. Nikki

I am an animal lover to the end.

Woodlawn, Chicago , IL, 60637

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

About: I'm an owner of a playful energetic nine year old boxer. Whenever you see me, you're sure to see my dog Marley. I'm very active so dogs usually ti... (more)

11. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"I was traveling out of town for two weeks in January and needed a pet sitter. Rebba was an amazing dog sitter to my beloved Mr. Jinx. She sent me daily photo... (more)"

12. TIANJIAO

Ariel's Dog Haven

South Side, CHICAGO, IL, 60637

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

4 repeat clients

About: I have a mastiff mix puppy named V, huge baby, incredibly sweet. I got her from Anti-Cruelty Society when she was four months old, raised her, trai... (more)

13. Katie

The best kind of walk is with a dog

Grand Crossing, Chicago, IL, 60619

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

"I really appreciate that I called Katie last minute and she was able to help me out with a last minute walk. Returned my message right away, I recommend Kati... (more)"

14. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care, 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)"

15. Charlyn

Puppy Dogs and Power walking FTW!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

About: I've been pet sitting and dog walking for a little over 4 years. I care for other people's pets because I can't own my own where I live. I've helpe... (more)

16. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"LeAnna was great with my dogs and kept me updated throughout the day. Thank you!! (more)"

17. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

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

"Blaize is an excellent petsitter. She's a kind, reliable, and thoughtful person--and a pet-owner herself. You'll have peace of mind when you're away from to ... (more)"

18. 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)"

19. Myk'La

Mind, face, and soul of a pup

Hyde Park, Chicago, IL, 60637

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)"

20. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"Tom would be awesome with your pets! He has had cats and dogs his whole life and could be trusted to take care of them. His pets are happy when he takes them... (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: