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.

1. Crystal Verified Background Check

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits

"Crystal did an amazing job with taking care of my cats and keeping me updated. I had some not great experiences with other sitters in the past but she went abo… (more)"

2. E Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

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

"She was great! Took great care of our big, energetic dog. Would definitely book again (more)"

3. Nataya Verified Background Check

Loving care when your not there!!

West Englewood, Chicago, IL, 60636

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

"Nataya was fantastic! She braved a very brutal winter storm to make sure my kitties were well fed and safe, and extended her care for a few days when I got stu… (more)"

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4. Beverly Verified Background Check

Home full-time, individual care

Chatham, Chicago, IL, 60620

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

"Bev was so awesome with my fur babies. She sent lots of pictures and kept me in the loop. I will definitely be booking her again ?? (more)"

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5. Kwaheem Verified Enhanced Background Check

Your Pet needs a vacation too.

South Shore, Chicago, IL, 60649

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

"I’m am a former client of Kwaheem’s and he made sure my dogs Ginger and Melo were in top take active shape and we never had a problem with him if it was him sp… (more)"

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6. Lesleigh Verified Background CheckRover 101

THE BEST BELLY SCRATCHES EVER!

South Chicago, Chicago, IL, 60617

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

"Lesleigh is one of this most caring and loving people I can rely on when it comes to watching and walking my dog Louis for me. Goes above and beyond to make su… (more)"

7. Allyssa Verified Background Check

Animal Lover

Hyde Park, Chicago, IL, 60637

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

"I trusted Allyssa to watch my dog, Prince, for a weekend, and he immediately cozied up to her. He has a few health issues which requires him to take medicines … (more)"

8. Valerie Verified Background Check

Animal lover with a heart of gold!

South Shore, Chicago, IL, 60649

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

"Hey my name is Doug me and my wife have two dogs while walking in dog park on lakeshore drive we all met Valerie playing with her two beautiful dogs her dogs a… (more)"

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9. Maeve Verified Background Check

Flexible schedule, big fenced yard!

Hyde Park, Chicago, IL, 60637

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

"Maeve was great! Very nice and easy going. You can tell she enjoys animals. Luna love her upon meeting her and her communication was great with photos and vide… (more)"

10. Derek Verified Background Check

I go above & beyond for pets.

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

About: I’m a animal and people person. I graduated from community college with an Associates in theatre arts. I’m available Tuesday’s, fridays and weekends.… (more)

11. Masheika Verified Background CheckRover 101

Crazy cat lady who loves dogs!

Hyde Park, Chicago, IL, 60615

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

"I was nervous about leaving a newly adopted dog and my 12 year old senior with someone so I did drop in visits and walks. Masheika was great with these two. S… (more)"

12. Roxy Verified Background Check

Dogs are a humans bestfriend.

Hyde Park, Chicago, IL, 60615

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

"Roxy was responsive, arrived as scheduled, and checked on our pets as requested. I also appreciate Roxy bringing in our mail packages that were left at the doo… (more)"

13. Samara Paula Verified Background Check

I'd love to take care of your pet

Hyde Park, Chicago, IL, 60615

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

"Samara is your perfect dog sitter without doubt! She love animals, especially dogs and cats. She is very responsible and patient. She loves to play and walk wi… (more)"

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14. Marcus Verified Background Check

Nice an happy!! Lets have some fun!

Woodlawn, Chicago, IL, 60637

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

About: Very patient. Also educated on dog feelings an health.. They say im a dog whisper 😃. I pay close attention to pet as far as if there mad or sick or d… (more)

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15. Aaliyah Verified Background Check

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

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

About: A true mommy dog lover.I have 2 small Maltese Poodles. Going away for the weekend or Holidays. Allow me to take care of your baby like my own. I live… (more)

16. Elizabeth Verified Background Check

Animal lover active animal activist

South Shore, Chicago, IL, 60649

Dog Boarding, Drop-In Visits, Doggy Day Care

About: Absolutely adore dogs! They are Sentient beings that are intuitive, innately kind and intelligent. Been an active member of peta and the human societ… (more)

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17. Chloe Verified Background Check

I vow to love your pets as my own!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"chloe was great! Super communicative and an amazing pet photographer :) I felt very safe having her look after my pet for the holidays and would totally ask he… (more)"

18. Sam Verified Background Check

Experienced Hyde Park Pet-Sitter!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"This was my fist time using "Rover", so I was a little nervous, but Sam did a great job. My cats are afraid of strangers. Sam sent me pictures of their lumps u… (more)"

19. Francesca Verified Background Check

Enthusiastic pre-vet student

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits

"Francesca is great. She is nice, great with my dogs and I would trust her to care for my dogs anytime. (more)"

20. Kat Verified Background CheckRover 101

Scientist who LOVES DOGS

Woodlawn, Chicago, IL, 60637

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

"Kat was great! I felt totally confident that my cats were being well taken care of, and she was super responsive and flexible during the stay. Thanks so much!! (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: