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

7 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

2. Haley

Young Professional Works from Home

Bridgeport, CHICAGO, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"My wife works as a reporter for a famous news agency and was on a long term assignment in the middle east when she was captured and imprisoned by some local ... (more)"

3. Shamika

Hello to all my pet parents

West Englewood, Chicago, IL, 60636

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

About: Hi i am a 30yr old pet lover i have always loved animals since i was a child, not to good with bugs, but cats, dogs, snakes, little furry things yo... (more)

4. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

2 repeat clients

"LeAnna is very professional, and did a great job looking after our little puppy, Isla. She is friendly, fun, and has tons of experience with caring for pets,... (more)"

5. Danielle

Providing and prioritizing your dog

Chicago Lawn, Chicago, IL, 60619

House Sitting, Drop-In Visits, Dog Walking

"Danielle, by far, has one of the greatest dispositions when it comes to working with pets. Being a pet owner, herself, she comes with the love, patience an... (more)"

6. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Our pups love Crystal and I can't imagine a better person to be part of our dog team. So grateful Crystal was able to help. (more)"

7. 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)"

8. Katie

Pup-loving college student

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've had pets all my life - dogs, cats, gerbils, snakes, you name it! I love animals and would take care of your dog as if it were my own. I love d... (more)

9. 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)"

10. 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)"

11. 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)"

12. Jinni

Skilled Pet Sitter & Photographer

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Although Jinni is my granddaughter and I must admit to being a bit partial, I would recommend her wholeheartedly for dog sitting. She has been an animal lov... (more)"

13. 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)"

14. 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)

15. Zachary

Available for you dogs needs.

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Zachary took care of my little two year old Labrador, Buster, while I was away on a business trip. He was very good with Buster and he definitely misses him.... (more)"

16. 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)"

17. Hanna

I will give your dog/s lots of hugs

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"I have known Hanna her entire life and what I have observed is what a loving and compassionate person she has grown up to be. She loves animals and is patien... (more)"

18. 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)"

19. 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)

20. Tyler

Love active dogs and

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Tyler has been my pet sitter for many years. He is extremely responsible and caring, and has gone the extra mile on more than one occasion, giving special ca... (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: