House Sitting in West Englewood, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed New Years Availability
1. Daniela

Reliable & Experienced Sitter

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Daniela is the best!! I have a 60 lbs Plott Hound and left to go out of the country for three weeks during which time Daniela stayed at my house. I came home... (more)"

Available this weekend
2. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

Available this weekend
3. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

Confirmed Holiday Availability
4. 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
5. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

6. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

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

1 repeat client

"Erin is an excellent sitter! She's very clearly an animal lover, and I feel completely at peace when I leave Rumi with her. (more)"

7. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Thank you Emily for taking care of Cali while we were gone! Emily was flexible with the hours we needed and gave us an update or two each day. We came home t... (more)"

Confirmed Holiday Availability
8. 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)

9. 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)"

Confirmed Holiday Availability
10. Kimberly

Your dog is my dog!

Roseland, Chicago, IL, 60619

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

1 repeat client

"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)"

11. Stephen

Walking, Bordering/Sitting Training

Beverly, Chicago, IL, 60643

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

7 repeat clients

"What a great service Stephen provided I don't think my dog even missed me much! A real dog lover who sincerely tried to help my big shelter dog with many issues (more)"

12. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

13. 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)"

14. 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)

Confirmed Holiday Availability
15. Giselle

I have a loving passion for dogs!

West Lawn, Chicago, IL, 60629

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

About: Hi, my names Giselle :)! I understand dogs to an emotional level, and I give them love and compassion as they deserve. I talk to my dogs, I give t... (more)

16. Jocelyn

Patient, playful and caring

Ashburn, Chicago, IL, 60652

House Sitting, Drop-In Visits, Dog Walking

"She is very friendly! Always talking about her pets! She loves them dearly. Ahe loves animals in general. As a person she's great to talk to, easy to get alo... (more)"

17. 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)

18. 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)

19. Maritere

My spirit animal is a mama dog!

Gage Park, Chicago, IL, 60632

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

About: I am a diligent, caring, and loving dog sitter. Dogs have always loved to be around me and I around them. I love to take care of cute pets and dogs... (more)

20. Teresa

Dog loving Chicago girl !

Chicago Lawn, Chicago, IL, 60629

House Sitting, Drop-In Visits, Dog Walking

"Teresa is someone who has such a love of animals, and dogs specifically, that I would personally feel like my own dog would be in the best of hands when in ... (more)"

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Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

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The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.