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Esteban O.

5.0 out of 5 stars
25 repeat clients
Profile image

Esteban O.

5.0 out of 5 stars
25 repeat clients

Contact for House Sitting

$139 total per night

These prices are for 1 dog, including a booking fee of 11%.

Highlights

Enhanced background check
11 years of experience
Can administer medication
Special needs experience
Senior dog experience
Can provide daily exercise

Pet care experience

Fairy Dogfather /all breeds & sizes

For over a decade, I’ve been pounding the pavement with many canine companions throughout Chicago. My experience as a petcare professional is vast and very varied: from puppy pals who have homes with yards to city canines in high-rise buildings with indoor dog runs; from toy poodles who can be a bit anxious or fearful to mountain mastiffs who tend to chase squirrels like a 20 pounder forgetting they are 200(!); from elderly newfoundlands who needed daily diaper changes to spry vishlas with boundless energy, whose sole purpose in life is to run you ragged; from mini French bulldogs who want to find new friends and think they are the leader of all packs, to pit bulls who consider themselves lap dogs; and from shiba inus who live for being aloof and alone to labradors that will happily lick your face clean off. Now, I’ve made a major move to the East Bay and am loving every minute of it. While I’ve left the wicked winter of the Midwest behind, I’ve brought with me all my experience and extensive references — a couple of companies and 75+ clients over the past 11 years. In the Windy City, I was able to hone my skills as a dog walker & pet sitter on the strength of my natural gifts of empathy and understanding, sense of adventure, and natural born chill & charm. Most people there know me by name (or at least by the iconic afro) and that goes double for the doggos. I’ll always love them and already miss them, but I’m excited to make new furry friends.

Qualifications

25 repeat pet parents
100% response rate
Usually responds in a few minutes
100% bookings with photo updates
Sends updates with Rover Cards
11 years of experience
Oral medication administration
Senior dog experience

Safety, trust & environment

I have an immaculate track record with my canine companions. Safety and trust are paramount in this business, so I require a meet and greet for all new clients. This allows owner, dog, and walker to feel each other out; address any needs, desires, and expectations; and make sure that location specifics are understood — from the surrounding neighborhood & house itself, to where leashes, bowls, treats, and toys are found within it.

Ratings and reviews

5.0
stars
81 ratings
Shelly B.
5.0 out of 5 stars
Dog Walking • Aug 04, 2026

Mags will miss you while we are away. Thank you for taking such good care of my little girl!!

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Brelyn H.
5.0 out of 5 stars
Dog Walking • Jul 07, 2026

Thank you again

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Azaleah G.
5.0 out of 5 stars
Dog Walking • Jun 29, 2026

Esteban saved the day!! Capri's other parent was out of town and I wasn't feeling well, and Esteban said "I got you!" and was here within 30 minutes of me reaching out. Capri clearly loved him, and he was friendly and professional. Will definitely be reaching out in the future!!

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Josephine I.
5.0 out of 5 stars
Dog Walking • Jun 20, 2026

My dog loved her walk with Esteban! Esteban is very friendly and professional, and I recommend his services.

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Liz K.
5.0 out of 5 stars
Dog Walking • May 18, 2026

Esteban is fantastic with my big dog leash reactive cocker spaniel. Gus is always so happy to see Esteban and comes back totally exhausted from his walks. Highly recommend!!

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Tanya W.
5.0 out of 5 stars
House Sitting • Apr 08, 2026

Our dog seems to have fallen in love. I said Esteban’s name and our pup was exited with big tail wags!

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Calendar and availability

Available
Not available
SMTWTFS
Available
Not available
SMTWTFS
SMTWTFS

Schedule

I have part time work that keeps my evenings and weekends pretty busy, so that frees up my mornings and afternoons for walks! As of now I’m open to taking on a half-dozen clients or so.

0 to 15 lbs
16 to 40 lbs
41 to 100 lbs
over 101 lbs
Esteban can host up to 1 pet per night
It’s always great to know behaviors and tendencies for walks: like how they behave around people and other pups. Once booked, knowing where leash, any weather-specific clothes, and whether to leave food/treats for the doggos is helpful as well.
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.

These prices are for 1 dog, including a booking fee of 11%.