House Sitting in Montclare, 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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1. BJ

Experience, Integrity, Compassion

Oak Park, IL, 60302

House Sitting, Drop-In Visits, Dog Walking

24 repeat clients

"BJ did an amazing job with Our dog while we were away for a week. She really spent a lot of quality time with Her. BJ even took Her to the vet because of a p... (more)"

2. Emily

Pooch lovin' lady!

Dunning, Chicago, IL, 60634

Dog Boarding, House Sitting

"You always want someone who will care for your dog as much as you do, and Emily is exactly that person. She is a huge dog lover and will care for every dog w... (more)"

3. Amber

Seeking Dog Buddies

Irving Park, Chicago, IL, 60641

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Amber was wonderful with Bailey. I was visiting Chicago with Bailey from Texas and need someone to watch him. Bailey immediately went to her and loved her!... (more)"

4. Jenny

Wet Nosed Approved

Park Ridge, IL, 60068

House Sitting

"Jenny has been an outstanding caregiver for my dog, Tito. She used to live across the hall in my apartment complex and was always offering to take Tito for w... (more)"

5. Anna

Dog Lover Seeks Playful Pups

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Anna has cared for our American Pitbull, Bonnie, on several overnight occasions when I've traveled out of town and we've always returned home to a happy and ... (more)"

Confirmed Holiday Availability
6. Devine

benevolent, disciplined, dedicated

Portage Park, Chicago, IL, 60641

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

2 repeat clients

"Devine is the most trustworthy, loving, and hardworking dog sitter I've had! My girls (elderly pug and chihuahua) just love her! I am able to relax when they... (more)"

7. Claire

Patient, energetic graduate student

Oak Park, IL, 60304

House Sitting, Drop-In Visits, Dog Walking

"Claire's love and compassion for animals runs deep. For as long as I have known her, she has always had a soft spot for animals of all kinds. I have witnesse... (more)"

8. Maria

Great Love and Attention with me

Jefferson Park, Chicago , IL, 60646

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

1 repeat client

"Maria is not just a dog lover,she is an animal lover! My 14 year old dog Jake absolutely hates water, let alone a complete bath! But he doesn't mind so much ... (more)"

9. Megan

Reliable, Respectful, Responsive

Austin, Chicago, IL, 60707

House Sitting, Drop-In Visits, Dog Walking

20 repeat clients

"Meg and Deb took the Rover experience up a notch with their professionalism and expert service. Not only did I receive daily text updates and photos, but ca... (more)"

10. Avery

Fun-loving, outdoorsy, and flexible

Portage Park, Chicago, IL, 60641

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

1 repeat client

"Avery absolutely adores dogs! He continuously plays with my dog and takes her out for bathroom breaks and/or more exercise. My puppy is always excited to see... (more)"

Confirmed New Years Availability
11. Katy

Love dogs- have references!

Irving Park, Chicago, IL, 60641

House Sitting, Drop-In Visits, Dog Walking

"Katy took great care of our two dogs over the holiday weekend! Sent us pictures and updates and had no issues while we were gone. The house was just as we le... (more)"

12. Rebecca

Artist Heart of Gold Caretaker!

Jefferson Park, Chicago, IL, 60630

House Sitting, Drop-In Visits, Dog Walking

"Beka has looked after my menagerie many times over the past 20 years. Presently, I have 4 dogs, 2 parrots, finches, a dove, 3 fish tanks, and a mali uromasty... (more)"

13. Justyna

Always early, never late.

Norridge , IL, 60706

House Sitting, Drop-In Visits, Dog Walking

"Justyna was great! Our dogs really enjoyed her. She was flexible with anything we needed. She took wonderful care of our fur babies. For which i am veey grat... (more)"

14. Lauren

Diamond & Friends @ Oak Park

Oak Park, IL, 60302

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Lauren was fantastic! She took really good care of our two pups. It seems like they miss her since I've been back more than they missed me when I was gone...... (more)"

Confirmed Holiday Availability
15. Bob & Ginger

Never Alone!

Norwood Park, Chicago, IL, 60656

Dog Boarding, House Sitting, Doggy Day Care

20 repeat clients

"Ginger responded quickly to our last minute need and even shuttled the dogs back and forth. She kept me updated on how and what they were doing and did a lot... (more)"

16. Luis

CPR and First Aid certified Cat/Dog

Portage Park, Chicago, IL, 60641

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

"Luis is my son and runs a dog business here through our house. I fully support him in all he does and love to meet all the dogs that come and go here at home... (more)"

17. Jessica

Caring and experienced dog sitter

Hermosa, chicago, IL, 60639

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

1 repeat client

"Jessica is a great dog sitter. I was out of town for a week and she came to my home to watch my 5 years old pitbull, Fiona. Fiona has a lot of energy and Jes... (more)"

18. Morgan

Zookeeper and pet sitter

Elmwood Park, IL, 60707

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"My husband and I needed to go out of town and our regular dog sitter was not available. We never used Rover.com before but someone at my office did and love... (more)"

Confirmed Holiday Availability
19. Evan

Please Try Me Your Pet Will Thank U

Elmwood Park, IL, 60707

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

"Evan has always been very trustworthy with our little family member (our 11 year old dog Jerry). Given Jerry's age and needs, my wife and I are very comfort... (more)"

20. Sierra

I am caring and in a love for dogs!

Elmwood Park, IL, 60707

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

2 repeat clients

About: I've grown up with dogs as small as Chihuahuas to as big as Great Danes! i volunteered at a couple animal shelters as well in Chicago. I've always ... (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.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

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.