Dog Walking in Oakland, Chicago

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Sitter Profile Image: Tamara J.
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Sitter Profile Image: Tamara J.
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1. Tamara J.

Star Sitter
Experienced Dog Owner
Grand Boulevard, Chicago, IL, 60653
0.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$22
per walk
5 out of 5.0 stars
66 reviews
23 repeat clients
Profile image

Tamara was really flexible with my last-minute request, and did a great job communicating and taking care of my elderly dog while I was out of town. I would definitely recommend her!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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2. Abi S.

Star Sitter
I’ll keep up with your pup!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
49 reviews
13 repeat clients
Profile image

No complaints! Still managed to get our dogs walked even with a broken finger! Loved the daily pics and updates. Was always on time. Would love to work with her again.

Availability updated 27 days ago
Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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3. Danielle B.

Star Sitter
I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
61 reviews
19 repeat clients
Profile image

Danielle had been great with Okami. He's usually very reserved and defensive with new people. But he warned up to her in just two walks. Bonus is that she takes tons of photos.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Samantha E.
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Sitter Profile Image: Samantha E.
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4. Samantha E.

RoverGO
Star Sitter
Professional Pet Sitter & Pup Lover
Hyde Park, chicago, IL, 60615
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 4.9 stars
82 reviews
47 repeat clients
Profile image

Samantha was awesome and took great care of our puppy, Layla. Looking forward to having her help us for any dog walking needs in the future!

Availability updated yesterday
Sitter Profile Image: Peyton W.
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Sitter Profile Image: Peyton W.
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5. Peyton W.

Here to care for your fur babies!
Grand Boulevard, Chicago, IL, 60653
1.2 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
7 reviews
2 repeat clients

Peyton took the BEST care of my cats when I went out of town. I’m the type of pet parent who has a lot of anxiety around leaving my fur babies in the care of anyone else. However, Peyton put my mind at ease with their attention to detail and frequent updates. I would highly recommend them!

Availability updated 6 days ago
Sitter Profile Image: Madison C.
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Sitter Profile Image: Madison C.
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6. Madison C.

Big dog lover who's home full time!
Kenwood, Chicago, IL, 60653
0.8 mi. away
Drop-In Visits, Dog Walking
from
$22
per walk
5 out of 5.0 stars
4 reviews
2 repeat clients
Profile image

Madison is so sweet, responsive, and enthusiastic. You can tell she really loves dogs! She always takes care of Jourdin on every walk she takes so I continue to book her for my doodle bear 💛

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Lisa "Rane" B.
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Sitter Profile Image: Lisa "Rane" B.
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7. Lisa "Rane" B.

All Creatures, Great and Small!
Kenwood, Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per walk
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Lisa "Rane" was fantastic with Bobby. She is prompt and personable. My dog received her well upon their first meeting. She and I developed a good rapport which led me to feel comfortable trusting her with Bobby. I will make her my first request when needing your service in the future.

Availability updated 2 days ago
Sitter Profile Image: Jordyn W.
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Sitter Profile Image: Jordyn W.
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8. Jordyn W.

Let’s make my dog jealous
Hyde Park, chicago, IL, 60615
1.7 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
3 reviews

Jordyn is a loving, responsible dog mom who is one of the most dependable, trustworthy people I know. She takes great pride in her work and is not afraid to show initiative to effectively problem solve. I highly recommend her! Your pet will love her.

Availability updated 17 days ago
Sitter Profile Image: Qutress T.
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Sitter Profile Image: Qutress T.
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9. Qutress T.

a dog-person without dogs
Grand Boulevard, Chicago, IL, 60615
1.4 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
66 reviews
21 repeat clients
Profile image

Qutress is so sweet to our Ellie and we are so lucky to have found her.

Availability updated 5 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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10. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per walk
5 out of 4.6 stars
8 reviews
2 repeat clients
Profile image

He was great with Bruno and food about communicating and being flexible with my schedule.

Availability updated 4 days ago
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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11. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
29 reviews
7 repeat clients

Elizabeth has watched my cat several times. She is excellent and extremely knowledgeable about animal care, and her prices are great. I will always use her if she's available!

Availability updated 9 days ago
Sitter Profile Image: ciara g.
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Sitter Profile Image: ciara g.
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12. ciara g.

Care for Four-legged Furry Friends
Kenwood, Chicago, IL, 60653
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
5 reviews
2 repeat clients

I've never seen a dog love someone as much as I've seen a dog love Ciara. She really has a way with animals, and always seems to make them comfortable, no matter the breed or the background. She really is a pet's best friend, and I'd recommend her to anyone.

Availability updated 16 days ago
Sitter Profile Image: Sophie R.
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Sitter Profile Image: Sophie R.
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13. Sophie R.

I only sit from one home at a time
Chicago, IL, 60642
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
2 reviews

We have 2 medically difficult cats and Sophie has been a godsend! She sends pictures frequently, follows all needs and doesn’t mind when we send her things in detailed notes. We hate being away from our babies but feel fine when Sophie has them!

Availability updated yesterday
Sitter Profile Image: Marlicia G.
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Sitter Profile Image: Marlicia G.
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14. Marlicia G.

Bachelors in Animal Science
Kenwood, Chicago, IL, 60615
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
4 reviews
2 repeat clients

About: Hi I’m Marlicia! I’m an experienced Veterinary Technician. I have over 9 years of experience in Vet Med & also possess a Bachelor’s degree in Animal Science. Animals have always been my passion & I am dedicated to improving their lives each & every day. I’m available usually on weekends but throughout the week as well. It depends on my work schedule but I am more then willing to accommodate your fur baby. I have a small puppy who gets along very well with other dogs. I also am fear free certified, so your pet will be in good hands.

Availability updated 2 days ago
Sitter Profile Image: Samira C.
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Sitter Profile Image: Samira C.
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15. Samira C.

Full time teacher and animal lover
Chicago, IL, 60653
1.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per walk
5 out of 5.0 stars
21 reviews
6 repeat clients
Profile image

Samira was amazing with Harlem. She communicated effectively, followed all of my instructions and ensured that he was happy in general. I would highly recommend Samira to anyone looking for a thoughtful caretaker for their pup

Availability updated 35 days ago
Sitter Profile Image: Candace M.
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Sitter Profile Image: Candace M.
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16. Candace M.

Rover 101
Star Sitter
Bronzeville Dog Boarding
South Side, Chicago, IL, 60653
1.0 mi. away
Boarding, Dog Walking
from
$25
per walk
5 out of 5.0 stars
14 reviews
7 repeat clients

About: Hello, My name is Candace and I have a 17 year old toy poodle by the name of Francesca. I adopted Francesca 12 years ago and instantly fell in love with her. She's a joy and I consider her family. I live in a 3 bedroom condo in Bronzeville, where I allow Francesca free access to roam. Your dog will have the same privileges. Your furbaby will be walked 2+ times a day and fed based on your specifications. And of course I will provide plenty of water for hydration. I prefer housebroken dogs but I am ok with dogs who use potty pads. If you're looking for a loving home to board your pet while you're away, this is the perfect place. I work mostly from home. I’m normally not away for more than a couple of hours. I can alert you to any change in this pattern. I can accommodate most requests. I will care for your dog based on your specifications. I treat all my guests like they’re my own dog.

Availability updated 35 days ago
Sitter Profile Image: WINDELL G.
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Sitter Profile Image: WINDELL G.
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17. WINDELL G.

Trusted Pet Care for Cats and Dogs
Douglas, Chicago, IL, 60609
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per walk
1 review

Windell is my “go-to” sitter for my 11 y/o mini schnauzer. He sends updates, along with photos and Max loves him like family! Thanks for caring for my baby like he’s your own!

Availability updated 2 days ago
Sitter Profile Image: Malayna M.
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Sitter Profile Image: Malayna M.
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18. Malayna M.

Attentive, Active, and Kind!
Chicago, IL, 60616
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$23
per walk
5 out of 5.0 stars
25 reviews
6 repeat clients
Profile image

Malayna has been friendly, available, and reliable when I need her. My dog likes her. I can recommend her as a sitter.

Availability updated 41 days ago
Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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19. Dee M.

Hyde Park Dog Lover
Grand Boulevard, Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
4 reviews
1 repeat client

Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I know she will get her exercise when she is with Dee. I cannot express enough how much I appreciate Dee & the genuine loving care she gives my little girl, Déjà. Highest recommendations from us!

Availability updated 7 months ago
Sitter Profile Image: Kelsie G.
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Sitter Profile Image: Kelsie G.
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20. Kelsie G.

Pawsitively the best dog care.
Grand Boulevard, Chicago, IL, 60605
0.5 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$20
per walk
4 reviews

Kelsie watched our furbaby, Roxie, due to my husband and my work schedules. Kelsie was a true blessing by being available to let her out and walk her as needed so she didn't have to stay locked up all day. Roxie loves Kelsie like family!!

Availability updated 66 days ago

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