Pet Setting & Drop Ins in Montclare, 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. Alexis

Cat lover misses hanging with dogs

Irving Park, Chicago, IL, 60641

Drop-In Visits, Dog Walking

"Alexis would be a fantastic addition to the Rover team. Not only does she adore dogs (and cats!), but she is environmentally conscious and would never dream ... (more)"

2. Andi

Dog Lover

Logan Square, Chicago, IL, 60647

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

1 repeat client

"I have known Andi for over 3 years now and she is one of the most kindhearted and caring people I know. One of the most incredible things about her is that ... (more)"

Confirmed Holiday Availability
3. Krystle

Family Missing Our Fur Baby!

Belmont Cragin, Chicago, IL, 60639

Dog Boarding, Drop-In Visits

About: We are a family of 5 with children (4, 10 & 13) who are begging us for a dog. Our own fur baby, Shadow went to doggy heaven earlier this year and o... (more)

Confirmed New Years Availability
4. Brittany

Professional Dog Bed

Irving Park, Chicago, IL, 60618

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

29 repeat clients

"Brittany was great! She came twice in one day to take our pup for a walk and we loved seeing the photos and updates. We will definitely use her again! (more)"

Available this weekend
5. Sapphire

Pets are Family,I will treat 'em so

Cicero, IL, 60804

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sapp hire did an amazing job. My dog was happy and treated well. I will be using her again!!! (more)"

6. Megan

Reliable, Respectful, Responsive

Austin, Chicago, IL, 60707

House Sitting, Drop-In Visits, Dog Walking

20 repeat clients

"We can't say enough about how wonderful our experience with Megan and Deb was. Our dog is elderly and has separation anxiety and we are sure he did not miss ... (more)"

7. Lauren

Diamond & Friends @ Oak Park

Oak Park, IL, 60302

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I believe that dogs are one of God's greatest gifts to mankind. Simply, they are family members! Growing up as an dog-lover, I chose jobs, such as ... (more)

8. James

Reliable Active & Responsible Male

Berwyn, IL, 60402

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"James was very good eith Raven. He made her feel comfortable and interacted with her well. (more)"

9. Kristina

A favorite aunt to your loved one

Dunning, Chicago, IL, 60634

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

24 repeat clients

"Kristina is awesome! She was such a sweetheart during out meet and greet and Hunter took to her right away. He's a puppy and thus has very high energy and s... (more)"

10. Annalee

A reliable, fun animal lover!

Hermosa, Chicago, IL, 60639

House Sitting, Drop-In Visits, Dog Walking

About: Hi there! I'm Annalee. I'm a college student and an animal-lover. I'm passionate, experienced and reliable. One of my favorite pet-sitting jobs I'v... (more)

11. Paola

Dogs are furry babies, I know :)

Norwood Park, Chicago, IL, 60630

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

2 repeat clients

"This was my first time using a dog walker. I can't thank Paola enough for doing this at the last minute for me...I had no stress at work worrying about my C... (more)"

12. Rebecca

Passionate About Paws

Norwood Park, Chicago, IL, 60656

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Rebecca is a loving, responsible and caring young woman. Her own pets are well cared for and spoiled as they should be. She would give spectacular care to an... (more)"

Confirmed Holiday Availability
13. Shannon

Zookeeper and Animal Care Provider

Elmwood Park, IL, 60707

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I'm a zookeeper by day, but have an extra soft spot for man's best friend! I've grown up with dogs and have extensive pet-sitting and dog-walking e... (more)

14. 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)"

Confirmed Holiday Availability
15. 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 excellent with dogs and has many years of experience. She cares for every pet with great proficiency and enthusiasm. Maria enjoys dog-sitting and sh... (more)"

Confirmed Holiday Availability
16. 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)"

17. Lisa

Best of care when you're not there!

Portage Park, Chicago, IL, 60630

Drop-In Visits, Dog Walking

"When it comes to animal care, compassion, and connectedness, there is no greater embodiment, than Lisa E. Her passion for animals of all genres, including o... (more)"

18. Jocelyn

Treating your dog like family!

Harwood Heights, IL, 60706

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Jocelyn walked our dog at my mother's condo while my husband and I were out of town. We had a mini crisis and she handled it with smarts and flexibility. We... (more)"

19. Morgan

Zookeeper and pet sitter

Elmwood Park, IL, 60707

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Morgan house sat for me and my husband while we were on our honeymoon. We came back to healthy and happy dogs and a gecko, plants that had been well cared fo... (more)"

20. Samantha

ATHLETIC-ENERGETIC-DOG LOVER

Belmont Cragin, Chicago, IL, 60639

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Great job with our puppy! Very responsible! (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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 Montclare, 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 Montclare, 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 Montclare, 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 dog sitter. 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 Montclare, 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: