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Jessica W.

Star Sitter

North Center, Chicago, IL

5.0 out of 5 stars
114 reviews
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Services

Jessica can host

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
Dogs over 1 year old
Spayed and neutered dogs only
No females in heat

Jessica can care for

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
over 101 lbs

Availability

I work in an office 2-3 days a week but can come home early if needed. Otherwise I have a flexible schedule and a backyard which allows for various dog walking options. I’m an active person so am happy to provide longer walks for the more active pups and also appreciate the rest if that’s not the right fit for your dog.

Available
Not available
SMTWTFS
Boarding Cancellation Policy:

About Jessica W.

Communication

25 repeat pet parents
100% response rate
Usually responds in a few minutes
70% bookings with photo updates
Sends updates with Rover Cards

Dog skills

4 years of experience
Oral medication administration
Injected medication administration
Can provide daily exercise

Safety, trust & environment

My home is a quiet one with just me with no other pets in the two bedroom condo. The four unit building has a fenced in backyard and there is a dog in the unit below me. I tend to allow dogs on furniture and to sleep in bed with me unless they or parents don’t prefer it. I enjoy taking dogs on long walks when their health and the weather allows and, if personality allows, may bring to visit family members or friends (no other dogs present).

Home

Lives in an apartment
Has a fenced yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 4-8 hours

Information Jessica W. would like to know about your pet

My building is an old one so we may hear neighbors walking around or in the hallway, especially at night. If your dog may be noise sensitive, especially if barking is a typical response, any tips on how to make the dog more comfortable is appreciated.

A typical day

Will typically start the day with a longer walk to help get nighttime energy out and do the same for the late afternoon/evening walk. Weather permitting, the fenced in backyard is a great place for dogs to run around and, if friendly with other dogs, can arrange a playdate with neighbor dogs. I have routes that I know will take 15 minutes, 30 minutes and up to an hour, depending on the dog’s pace, so it’s a nice way to explore the neighborhood. With dogs that are comfortable with other dogs, I may take them to visit my dad in Streeterville who loved the company of my furry charges!

Location

Chicago, IL

Jessica W.'s Neighborhood

Jessica W. 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.

Former dog foster turned sitter!

Pet care experience

The past ten years have included watching family and friends’ dogs here and there with sizes ranging from 8 lbs to 50-60 lbs. Over the past year, I decided to start fostering dogs and have since cared for three foster dogs (one of whom was deaf) and six friend dogs (while they traveled) for times ranging from 36 hours to six weeks. Some dogs were very friendly with other animals and people and some were less so and had a small bit of leash aggression so I learned to try and redirect and reinforce good training.

Reviews

Nancy M.
Boarding • Aug 17, 2026
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Gus loves his stays with Jessica! Jessica is great with providing updates. We always feel super comfortable leaving Gus knowing he’s in good hands.

Clare F.
Boarding • Jun 18, 2026
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Jessica is an absolute top-tier dog sitter. She has been caring for my dog for a few years and has always made me feel a sense of solace while I am out of town. My dog treats her house as a second home and she treats him like her own. He never looks back after drop off and even hogs the bed! If you are looking for a lovely, communicative, and super normal person to care for your pet as you would, Jessica is the right choice! I am moving away and Jessica has set the standard for all my future dog sitters. Thank you, Jessica!

Nancy M.
Boarding • Apr 27, 2026
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Jessica is an amazing sitter! Great communication and pics throughout the stay. Gus looked like he settled right in 🙂

Lunden S.
Dog Walking • Apr 26, 2026
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Always happy to have Jessica take care of my girl. She was sensitive to changes and gave great communication and updates.

About Jessica W.

Communication

25 repeat pet parents
100% response rate
Usually responds in a few minutes
70% bookings with photo updates
Sends updates with Rover Cards

Dog skills

4 years of experience
Oral medication administration
Injected medication administration
Can provide daily exercise

Safety, trust & environment

My home is a quiet one with just me with no other pets in the two bedroom condo. The four unit building has a fenced in backyard and there is a dog in the unit below me. I tend to allow dogs on furniture and to sleep in bed with me unless they or parents don’t prefer it. I enjoy taking dogs on long walks when their health and the weather allows and, if personality allows, may bring to visit family members or friends (no other dogs present).

Home

Lives in an apartment
Has a fenced yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 4-8 hours

Information Jessica W. would like to know about your pet

My building is an old one so we may hear neighbors walking around or in the hallway, especially at night. If your dog may be noise sensitive, especially if barking is a typical response, any tips on how to make the dog more comfortable is appreciated.

A typical day

Will typically start the day with a longer walk to help get nighttime energy out and do the same for the late afternoon/evening walk. Weather permitting, the fenced in backyard is a great place for dogs to run around and, if friendly with other dogs, can arrange a playdate with neighbor dogs. I have routes that I know will take 15 minutes, 30 minutes and up to an hour, depending on the dog’s pace, so it’s a nice way to explore the neighborhood. With dogs that are comfortable with other dogs, I may take them to visit my dad in Streeterville who loved the company of my furry charges!

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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Jessica W.

Star Sitter

North Center, Chicago, IL

5.0 out of 5 stars
114 reviews