Pet Setting & Drop Ins in West Englewood, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

2. Jen

Offering love all day, every day!

West Lawn, Chicago, IL, 60629

Drop-In Visits, Dog Walking

About: My name is Jennifer, but feel free to call me Jen! I'm 24 years old and have experience with dogs for over 10 years. I'm a true believe that dogs a... (more)

3. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 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)"

Confirmed Holiday Availability
4. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

Drop-In Visits, Dog Walking

1 repeat client

"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)"

Confirmed Holiday Availability
5. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was great with a little doggie who is mostly afraid of people. Little Jax warmed up to her and she took great care of him. 5 Paws for Moesha (more)"

6. Stephen

Walking, Bordering/Sitting Training

Beverly, Chicago, IL, 60643

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

7 repeat clients

"I really appreciated Stephen's updates about our Frank and the photos he sent! He did more than just let Frank out to use the bathroom- he bonded with him! I... (more)"

Confirmed Holiday Availability
7. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

"Kimberly was first responsible for dog sitting my fur baby Sascha during a 2 week honeymoon period. She did an excellent job. My dog (Yorkie) is very parti... (more)"

8. Noreen

Loving and fun dog sitter!!

Beverly, Chicago, IL, 60643

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

12 repeat clients

"My mom's loves for dogs is awesome! On top of always being there for us, she is always looking out for the dogs that she is watching. Whenever I am home, I t... (more)"

Confirmed Holiday Availability
9. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

About: I moved to Chicago from Gainesville, FL to get a fresh perspective and a change of pace. I'm an artist who spends most of my time making comics and... (more)

10. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

" Emily has been in the dog-caretaking business for four years. There is nobody I'd recommend before her. Not only is she extremely trustworthy on all levels... (more)"

Confirmed Holiday Availability
11. Frank

Play date with the boys!

West Elsdon, Chicago, IL, 60629

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

40 repeat clients

"Frank goes above and beyond... And his gentle and calm demeanor will put you at ease right away. He is a good person... Dogs like him. And I trust him. :) (more)"

Confirmed Holiday Availability
12. Myk'La

Energetic, artsy, happy and caring

Chatham, Chicago, IL, 60619

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)"

Confirmed Holiday Availability
13. Megan

Pets are my life! I love them!

Chicago Lawn, Chicago, IL, 60629

House Sitting, Drop-In Visits, Dog Walking

About: I have owned dogs my whole life. I got my first dog as a Christmas present when I was in third grade. Ever since then, I have been taking care of m... (more)

Confirmed Holiday Availability
14. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have 14 years experience with a variety of animals, including exotics. I have taken care of animals with special needs and medications. While i... (more)

Confirmed Holiday Availability
15. Samantha

Your dogs vacation spot!

Gage Park, Chicago , IL, 60632

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

"Samantha is amazing!! She was great at communicating, sent pictures, always kept me updated. I loved how quickly she responded to my texts and calls. I felt ... (more)"

16. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is an angel! She loves my sweet baby Ray like one of her own. Sarah has watched Ray on multiple occasions. During their time together she often takes h... (more)"

17. Gabriela

Dog-owner that loves animals dearly

West Elsdon, Chicago, IL, 60632

House Sitting, Drop-In Visits, Dog Walking

About: My family has owned pets for all of my life. I had to start caring for my own dogs starting at 8 years old. I currently own three wonderful dogs an... (more)

18. Rosalie

wonderful dog handler, cozy home

Chicago Lawn, CHICAGO, IL, 60629

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

"Rosie has an outstanding relationship with all pets she encounters. She is loving, caring, and goes above and beyond. She is never fearful and will do whatev... (more)"

19. Brenda

Punctual and passionate dog lover

Chicago Lawn, Chicago, IL, 60629

House Sitting, Drop-In Visits, Dog Walking

About: I have grown up with dogs for the majority of my life. They've always had a special place in my heart. Dogs don't judge us they just want to make u... (more)

20. Randi

Loved animals all my life.

West Englewood, Chicago, IL, 60636

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

About: Hi everyone my name is Randi I am a 22 year old college student and I enjoy animals especially dogs and cats. I think its because they show you how... (more)

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Learn About Premier

Dog owners in West Englewood, Chicago, IL turn to pet sitters on Rover.com for their pet sitting needs. Over 7,915 pet owners have reviewed pet sitters in Chicago, giving them an average rating of 4.9/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Chicago with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving West Englewood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in West Englewood, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy West Englewood pet sitters and avoid the kennel.

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 West Englewood, 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: