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Drew B.

Star Sitter

Chicago, IL

5.0 out of 5 stars
28 reviews
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Services

Drew can care for

Cats
0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
over 101 lbs
Dogs over 1 year old

Availability

First and foremost, I do not have a car and will take public transit to and from your place. Unfortunately, the map function here isn't great. So, there might be some areas that are listed as inside my radius that I might not be able to accept. I do also have a bike that I use frequently. Bonus points if you're within a 20-to-30-minute bike ride Ravenswood I can work remotely during the week for my day job so can be available to let animals out frequently if needed. It would ideal if you had an adequate home office set up. Especially for longer stays. It doesn't have to be anything fancy, just a proper desk and chair. Working, say, from a dining room table, or a counter height bar with a table height chair, will not work. Bonus points if you have an extra monitor. Extra bonus points if you have a Switch dock. Extra extra bonus points if you have bidet, lol!

Available
Not available
SMTWTFS
House Sitting Cancellation Policy:

About Drew B.

Communication

3 repeat pet parents
100% response rate
Usually responds in under half an hour
100% bookings with photo updates

Skills

9 years of experience
Oral medication administration
Can provide daily exercise

Safety, trust & environment

Making sure animals get proper exercise and stimulation is what drives me to having and taking care of pets! But I know that's different for each and every pet.

Information Drew B. would like to know about your pet

I'd like to know their temperament especially when it comes to walking them. How will they react to other dogs or people? Should I be cautious when other dogs or people are approaching or are they very friendly? Can they be taken off leash at a dog park and allowed to run around and play with other dogs?

A typical day

Walking and playing a lot! I love to play tug or fetch and just generally keep dogs occupied. I can also provide your dog with plenty of snuggles if they like!

Location

Chicago, IL

Drew B.'s Neighborhood

Drew B. has Star Sitter status

The Star Sitter program highlights responsive sitters who deliver highly rated care and have a history of listing accurate availability and preferences, making it easier for pet parents to find the best care for their pets.

Let Me Take Great Care of Your Dogs

Pet care experience

I grew up with dogs my whole life. Taking them out for walks and the like. While I don't have dogs now, whenever I go home to visit my parents, I love taking the dogs for walks, keeping them occupied and playing with them! I especially like to see dogs happy and well exercised. I also like to keep them socialized and love giving them plenty of time to run around and play with, especially with other dogs if that's doable.

Cat care experience

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Let me spend time with your cat!

Drew also cares for cats. Learn about their cat-specific care experience.

Reviews

Cassie W.
House Sitting • Jun 29, 2026
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Drew took great care of our pup while we were away! He was responsive and sent updates each day so we could relax and know our dog was in good hands.

Madison P.
House Sitting • May 11, 2026
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Drew was very responsive and did a wonderful job watching our pets!

Amanda L.
House Sitting • Apr 05, 2026
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Drew was prompt, responsive, and helpful with giving the dogs medication and care! He left my place clean and ready for my return. Highly recommend!

Sarah B.
House Sitting • Mar 31, 2026
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Drew was super! He took incredible care of our two dogs and house while we were away. He was respectful and considerate and made sure our pups got lots of love!

About Drew B.

Communication

3 repeat pet parents
100% response rate
Usually responds in under half an hour
100% bookings with photo updates

Skills

9 years of experience
Oral medication administration
Can provide daily exercise

Safety, trust & environment

Making sure animals get proper exercise and stimulation is what drives me to having and taking care of pets! But I know that's different for each and every pet.

Information Drew B. would like to know about your pet

I'd like to know their temperament especially when it comes to walking them. How will they react to other dogs or people? Should I be cautious when other dogs or people are approaching or are they very friendly? Can they be taken off leash at a dog park and allowed to run around and play with other dogs?

A typical day

Walking and playing a lot! I love to play tug or fetch and just generally keep dogs occupied. I can also provide your dog with plenty of snuggles if they like!

Each sitter joining Rover needs to pass a background check. And by booking on Rover, you can get photo & message updates, 24/7 support, and reimbursement for eligible vet care.
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Verified Enhanced Background Check
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Verified Enhanced Background Check

Drew B.

Star Sitter

Chicago, IL

5.0 out of 5 stars
28 reviews