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.

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Tina did a great job taking care of our two cats while we were out of town for a long weekend! She was very responsive to our requests and was readily availa... (more)"

2. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

17 repeat clients

"Enoch is a very professional cat sitter. He knows a lot about how to communicate and play with cats. I feel very comfortable to leave my cats with him. He fe... (more)"

3. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"I have come to know Craig as a good and caring person. I have witnessed him interacting with dogs on several occasions and he has displayed genuine concern f... (more)"

4. Danielle

Providing and prioritizing your dog

Chicago Lawn, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

"Danielle Rupert is an absolutely wonderful dog sitter. Very loving and caring spirit. She has a special love for animals and wants them to be treated with th... (more)"

5. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

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

"We went away for a several week vacation, and Tom was amazing with our fearful dog. Our dog has a disability, is fearful of strangers in her home, and can re... (more)"

6. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Crystal is the ideal cat sitter, she loves animals and I had no doubt my cat was in caring hands while I was out of town. (more)"

7. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

Dog Boarding, House Sitting, 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)"

8. Eva

Lifetime Dog Lover & Future Vet!

Kenwood, Chicago, IL, 60515

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I have known Eva for several of years, we are great friends and there is no other person I would recommend to watch my pet besides her. I would allow her to ... (more)"

9. Lily

Diligent student with experience

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"If I would trust anyone with my pet, it would be Lily. She is so responsible and on top of things that I know she would give the utmost care to my dog. Also,... (more)"

10. Alejandra

College student w/ a love for pups!

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

2 repeat clients

"Alejandra is one of the most caring and gentle people I've had the pleasure of knowing, and it's a fact that she spreads her loving nature to fellow humans a... (more)"

11. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly took great care of my cats, Fisher and Bugaloo. I appreciated the daily updates and photos. They had plenty of food and water when I returned home. Hig... (more)"

12. 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)"

13. Amy

Grad student seeking puppy cuddles

Woodlawn, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Amy was great when I hired her to walk my dog during the day. My dog Bruno loves to walk but also loves to pull. Amy had no problem handling him during the w... (more)"

14. Aaliyah

Dog Care Chicago

Grand Crossing, CHICAGO, IL, 60621

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

1 repeat client

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 ... (more)

15. Nathan

Your dog is my number one priority.

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"To Whom It May Concern: It is my pleasure to provide a reference for Nathan. He has always been very comfortable with all of my dogs as well as my famil... (more)"

16. Blaize

Blaize's Dog Sitting in Hyde Park

South Side, Chicago, IL, 60637

House Sitting, Drop-In Visits

"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)"

17. Nicole

Happy to help and flexible schedule

Kenwood, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

About: Grew up with dogs, raised my own, and love 'em to bits! I wish I could keep mine in my apartment, but I am more than happy to help care for yours w... (more)

18. Joni

I'll run, play, laugh with your dog

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

About: I come from a large extended family of dog-fanatics. I've grown up walking, jogging, playing, snuggling, and socializing with dogs of all kinds, ag... (more)

19. Zachary

Available for you dogs needs.

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Zach is great with animals! He watched my dog for two weeks and when I got back my dog loved him more than me. Would recommend him to anyone! (more)"

20. Myk'La

Mind, face, and soul of a pup

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

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: