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. Joy

Your Dog Will Be Loved!

South Shore, chicago, IL, 60610

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

6 repeat clients

"Joy is awesome! She was punctual and when I needed her to assist me with my Rupert for an emergency she didn’t hesitate to respond and help. She sent picture... (more)"

Confirmed availability
4th of July
2. Dee

Hyde Park Dog Lover

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I ... (more)"

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3. Samone

I went to school for this! :)

Grand Crossing, Chicago, IL, 60619

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

1 repeat client
No Reviews Yet

About: My experience with pet health care started very early on as a child, as my mother was a Veterinarian Technician, and allowed me with an abundance o... (more)

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4. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"Alex was fantastic! He went the extra mile for us, patiently waiting for me to drive to our house when there was an issue with gaining entry. Koffee quickly ... (more)"

Confirmed availability
This weekend
5. Rosa

Experience with Geriatric Dogs

South Shore, CHICAGO, IL, 60649

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

"You cannot do any better than Rosa for caring for your pet when you are not available. She is excellent and perceptive for an animal's needs and is the MOST ... (more)"

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6. Dwight

Work from home - large fenced yard

Woodlawn, Chicago, IL, 60637

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

2 repeat clients

"Dwight has done a wonderful job with my dog and my best friends dog when he offered to take them both at short notice. The dogs loved him and he sent a phot... (more)"

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7. Christal

I’m @ home full time

Kenwood, Chicago, IL, 60615

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

About: Hi, I’m Christal and I am looking forward to being your next pet-sitter! I walked dogs professionally for years and have recently picked it back up... (more)

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8. Margot

Keeping those tails wagging!

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Margot is an amazing pup sitter! Our two young lads, golden retriever siblings, thoroughly enjoyed having her come and stay with them. They were always happy... (more)"

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9. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Nina took good care of my two cats while I was on Vacation in Florida for a week! She is very reliable. (more)"

Confirmed availability
4th of July
10. 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)

Confirmed availability
4th of July
11. Thandaway

Pre-vet student majoring in cuddles

South Shore, Chicago, IL, 60649

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Thandaway was amazing! She took pictures everyday she visited for me! My kitty is usually quite shy, but she warmed up quickly to Thandaway. I’ll definitely ... (more)"

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12. Samantha + Mac

Looking for new friends!

Hyde Park, Chicago, IL, 60615

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

"I have known Samantha for over 15 years and pets have always been a part of her life, both dogs and cats. Her pets have always been very happy, well-trained... (more)"

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13. Eve

dog lover :)

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Eve is one of the biggest animal lovers I know. She has many cats and a dog that she spoils. I remember when there was a cat at the animal hospital that she ... (more)"

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14. Kyisha

Home full time, large fenced back y

Englewood, Chicago, IL, 60637

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

1 repeat client

"It's a blessing having someone like Kesha around, she's very easy going with my dog, most of the time I have a hard time trying to get my dog to leave kesha,... (more)"

15. Lillian

Flexible Schedule - Loves to walk!

Hyde Park, Chicago, IL, 60637

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

About: Hi there! My name is Lily I'm a recently graduated University of Chicago undergraduate. I've got a very open schedule to take care of your best fr... (more)

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16. Alexandria

LOVE BIG DOGS (especially huskies )

Kenwood, chicago, IL, 60615

Drop-In Visits, Dog Walking

"Alexandria is very responsible and trustworthy, I go to her for all my pet sitting needs. My dog Emi really enjoys Alexandria and behaves so well when she is... (more)"

17. Dominique

Love given, Love needed, Love dogs!

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"I've only known Dominique a few years but before my Lily passed on she was always great with her. I've never actually PAID her to watch Lily but she loved Do... (more)"

Confirmed availability
This weekend
18. 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)"

19. Katie

dog-loving student

Hyde Park, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

About: I'm a grad student with a wonderful, 4yo dog. He loves other dogs more than anything, and so do I. After bad experiences with boarding facilitie... (more)

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20. Andrea

Dogs love my peaceful personality!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Andrea is a caring, self-motivated, and efficient person who knows how to work productively in stressful and new environments. She has told be about her pass... (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: