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Olivia D.

Lake View, Chicago, IL

5.0 out of 5 stars
41 reviews
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Services

Olivia can host

Cats
0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
over 101 lbs
Dogs over 1 year old
Crate-trained dogs only

Olivia can care for

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

Availability

I am pretty flexible and available during the week since I work a hybrid job. I live with my partner, Sage, who is also a Rover sitter & works remotely, so your dog(s) will receive double the care & attention while in our care! I enjoy going on long walks or runs and would love to have some canine company. I am open to regularly scheduled walks/visits.

Available
Not available
SMTWTFS
Boarding Cancellation Policy:

About Olivia D.

Communication

8 repeat pet parents
68% response rate
Usually responds in under 12 hours
30% bookings with photo updates
Sends updates with Rover Cards

Dog skills

23 years of experience
Oral medication administration
Injected medication administration
Senior dog experience
Special needs dog experience
Can provide daily exercise

Safety, trust & environment

I love to give dogs plenty of attention & make sure to closely follow any care instructions given. My partner Sage loves to be involved when we board dogs, so you can rest assured your pet will receive extra care and love while in our home! Whenever I housesit, I always leave someone’s home as I found it, if not better! I will send lots of pictures & updates throughout the service to reassure you that your pet is in good hands while you’re away. I do not have any pets & I’m happy to offer pet sitting care at a client’s home or boarding. I also have a lot of experience caring for more reactive, aggressive, or unpredictable dogs who need to avoid interacting with other dogs outside the home.

Home

Lives in an apartment
Does not have a yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 2-4 hours

Information Olivia D. would like to know about your pet

Let me know if there are any behavioral characteristics or challenges I should be aware of before meeting your dog, as well as any behaviors you’re working to improve.

A typical day

I like taking long walks and enjoy walking or running the Lake Front Trail! I love going on fun adventures with dogs, whether it’s a park or a farmer’s market, I love to get outside! I know how to handle dogs of all different sizes and ages and truly never get tired of playing with them.

Location

Chicago, IL

Olivia D.'s Neighborhood

Huge dog lover & flexible schedule!

Pet care experience

I have been professionally dog walking & sitting for over 4 years, so you can trust me to take great care of your pet(s)! I grew up with dogs and a ton of other pets (at one point we had a dog, rabbit, bird, hamster & fish!). I’m very active and have a lot of pet care experience— including dog walking & cat sitting for neighbors since I was little! After losing my family dog, I started doing Rover and have found it very rewarding. I would love to get a dog one day but until I am ready, caring for your beloved dogs or cats brings me so much happiness!

Reviews

Kelly R.
House Sitting • Aug 22, 2026
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Olivia was absolutely wonderful with our Bella! Bella has a lot of anxiety, especially when we travel, so finding someone who understands her needs and makes her feel safe and comfortable is incredibly important to us. Olivia gave her so much love and attention, took her on fun walks to the park and lake, and really took the time to understand what Bella needed. It gave us such peace of mind knowing she was being so well cared for while we were away. We came home to a very happy girl! We are so grateful to Olivia and would absolutely recommend her to anyone looking for someone kind, attentive, and genuinely caring to look after their pets.

Ally B.
Boarding • Aug 20, 2026
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Olivia and her partner, Sage, were great! They are great communicators who provided lots of updates and photos, which we always really appreciate. They were very patient with our 1 year old pup, Hudson, and gave him lots of attention and love. Would recommend Olivia and would certainly book again!

Cara A.
House Sitting • Jul 23, 2026
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Olivia has stayed with my pup twice now and she’s been a dream! Love all the updates/photos and took extra care when Augie was feeling under the weather this last time.

pat o.
Boarding • Jul 07, 2026
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Olivia was the absolute best! She cared for Bruce like he was her own and it made us feel so comfortable leaving him. She sent so many updates and pictures that we felt like we were even there!

About Olivia D.

Communication

8 repeat pet parents
68% response rate
Usually responds in under 12 hours
30% bookings with photo updates
Sends updates with Rover Cards

Dog skills

23 years of experience
Oral medication administration
Injected medication administration
Senior dog experience
Special needs dog experience
Can provide daily exercise

Safety, trust & environment

I love to give dogs plenty of attention & make sure to closely follow any care instructions given. My partner Sage loves to be involved when we board dogs, so you can rest assured your pet will receive extra care and love while in our home! Whenever I housesit, I always leave someone’s home as I found it, if not better! I will send lots of pictures & updates throughout the service to reassure you that your pet is in good hands while you’re away. I do not have any pets & I’m happy to offer pet sitting care at a client’s home or boarding. I also have a lot of experience caring for more reactive, aggressive, or unpredictable dogs who need to avoid interacting with other dogs outside the home.

Home

Lives in an apartment
Does not have a yard
Non-smoking household
Has no pets
No children present
Dogs allowed on bed
Dogs allowed on furniture
Potty breaks every 2-4 hours

Information Olivia D. would like to know about your pet

Let me know if there are any behavioral characteristics or challenges I should be aware of before meeting your dog, as well as any behaviors you’re working to improve.

A typical day

I like taking long walks and enjoy walking or running the Lake Front Trail! I love going on fun adventures with dogs, whether it’s a park or a farmer’s market, I love to get outside! I know how to handle dogs of all different sizes and ages and truly never get tired of playing with them.

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

Olivia D.

Lake View, Chicago, IL

5.0 out of 5 stars
41 reviews