Dog Walking in Oakland, Chicago

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1. Crystal R.

My home is where your pet is.
Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
89 reviews
39 repeat clients
from
$23
per walk

Chrystal is very caring and my dog Bear loves her. She is an experienced walker. She is also a great communicator and is very conscientious. I would highly recommend her.

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Sitter Profile Image: Sidoni G.
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Sitter Profile Image: Sidoni G.
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2. Sidoni G.

Happy human for happy pups!
Lower West Side, Chicago, IL, 60608
4.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per walk

Sidoni is by far one of the best persons to have your lil pup be around. She treats your little one as though it was her own. Sidoni is incredibly responsive and sends you a detailed info of her stay with your littles. I would highly recommend her and am incredibly happy that we found her in Rover.

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Sitter Profile Image: Carmen P.
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Sitter Profile Image: Carmen P.
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3. Carmen P.

A dog-less dog lover
Woodlawn, Chicago, IL, 60637
3.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
6 repeat clients
from
$20
per walk

Very kind and accommodating

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Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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4. Michael D.

Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
4.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
8 repeat clients
from
$20
per walk

Michael is best walker I've found on this app. He caters to my dog as if he was his own.

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Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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5. David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
78 reviews
32 repeat clients
from
$20
per walk

He came in last minute as I was out of town . Communication was prompt and clear. I felt safe with him caring for my pup while i was away. Thank you and for all the pictures which mean so much

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Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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6. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$18
per walk

Chijioke is one of the most caring and empathetic caregivers I have ever met. My cat easily fell in love and felt safe around them for cuddles and play times. They took extra care to make sure she and her litter space were clean. As well as training her on what are her dedicated spaces versus where she's not allowed like in the bathroom tub lol They have been super helpful in guiding me on how to be a better pet parent every time we meet. Very grateful to have them as my and my cat's best friend!

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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7. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$18
per walk

About: Pet care should be stress-free with the guarantee that your furry family member is getting the attention and activity they need. For 15 years I have taken on pet care opportunities that centered around the schedule and needs of the pups. We have a dog with epilepsy, so we know the importance of having pet sitters you can trust. My experience can be used to help pet owners feel at ease when they are away from their pets with various medical or senior needs. Looking to share my extra time with some pups during a transitional season in life! Caring for pets can take up most of my week if needed. My availability to stay overnight is limited to 1-2 nights at the moment due to my living situation. It is very important to establish trust with any animal I am walking or watching. I recommend spending at least 15min on a walk or in your home to get to know the way they move around the space or the neighborhood with new people. I am prepared to follow any training instructions you have set in place for your dog so they can continue the good habits while you’re away. Keeping things consistent and calm is important to me!

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Sitter Profile Image: Andres R.
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Sitter Profile Image: Andres R.
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8. Andres R.

I care for your pets as my own!
Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
2 repeat clients
from
$14
per walk

Punctual and communicative. :-)

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Sitter Profile Image: Isis "Ra" F.
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Sitter Profile Image: Isis "Ra" F.
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9. Isis "Ra" F.

I love all animals, especially dogs
Chicago, IL, 60653
0.8 mi. away
Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$20
per walk

Super responsive & accepted my booking on a last minute basis. I enjoyed the communication & pictures & I feel that my dog was well cared for. I would absolutely book again. Thank you for the care! 🫶🏽

Sitter Profile Image: Brittany W.
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Sitter Profile Image: Brittany W.
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10. Brittany W.

Attentive, patient & open-minded!
Near South Side, Chicago, IL, 60616
2.5 mi. away
Doggy Day Care, Dog Walking
1 repeat client
from
$18
per walk

Brittany has always had a love for dogs and it shows! I have two dogs, one over 90 lbs and another over 45 lbs and she gets along with them splendidly. Brittany has played with them and taken them out on walks in the past with no issue. I'm happy to trust her with my furry family members.

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Sitter Profile Image: Kaitlin R.
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Sitter Profile Image: Kaitlin R.
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11. Kaitlin R.

Your pet comes first!
Hyde Park, Chicago, IL, 60615
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
9 repeat clients
from
$25
per walk

Kaitlyn is the only walker on Rover that I would actually have a key cut for. She is very professional, punctual, and respectful with your pup.

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Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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12. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk

Jabari is currently a co-owner of a 8-12 month old Yorkshire Terrier mix currently alongside me whom he frequently feeds, grooms and bonds with on a daily basis. Jabari has experience with both large and small breeds of dogs, he has worked with 1+ year old male Pure breed Cane Corso and 1+ year old female German Shepherd Mix who he has cared for and watched over several times over their life. As well as, already pet-sitting a variety of dogs for many owners within his own family. I would highly recommend Jabari for care for other's pets as he is responsible, caring and diligent about the well-being of all pets and properly caring for them according to their breeds, sizes and ages.

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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13. Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60616
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
86 repeat clients
from
$30
per walk

Thanks to Dalila! My dog had only been walked by friends he knew well. Dalila did a meet and greet, but he was still unsure when she came over. She used treats and gave him time to warm up and got him out! She reads dog language well and is patient with nervous doggos like my boy.

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Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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14. Danielle B.

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
$20
per walk

I've known Danielle now for a few years, and I can confidently recommend her as a responsible pet caregiver! Growing up in a home full of dogs, she is no stranger to the hard work and dedication it takes to lovingly care for any pet! And it clearly shows with how happy those dogs are!

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Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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15. Elizabeth D.

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

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!

Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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16. Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$25
per walk

Kayla is amazing she is super communicative leaves really awesome notes and takes amazing pictures. Best part is she does this with a smile on her face! Kayla really enjoys spending time with dogs

Sitter Profile Image: Olivia M.
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Sitter Profile Image: Olivia M.
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17. Olivia M.

Hi I’m Olivia and I love your pets
Chicago, IL, 60616
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$15
per walk

Olivia is great with animals! I remember one time when we were driving together, we saw a dog running on the side of the road. They stoped the car and went on a quest to find the owner. They are an also a devoted pet parent to Wolf, a sassy cat with a wholeeeee lot of personality. Olivia is a caring and nurturing presence, and If you book with her, you will won’t be disappointed.

Sitter Profile Image: Toni B.
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Sitter Profile Image: Toni B.
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18. Toni B.

There for your pet, there for you !
Chicago, IL, 60653
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
1 repeat client
from
$17
per walk

Toni was so easy to work with and professional from start to finish. Her communication style is thorough but to the point. This was my first time using Rover, so she easily guided me through the processes by asking me the necessary information. My initial communications with Toni put me more at ease with leaving my pup, and after our in-person meeting I no longer had concerns with leaving him for the day. I loved getting several photos and thorough reports of the walks. I’d definitely hire her again!!

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
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per walk

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!

Sitter Profile Image: Valeria V.
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Sitter Profile Image: Valeria V.
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20. Valeria V.

Walk, play, cuddle and repeat!
Grand Boulevard, Chicago, IL, 60605
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$15
per walk

About: I’ve taken care of and lived with dogs of all ages, breeds and sizes. I enjoy spending lots of time on walks, runs, play, and cuddles! I currently work from home 3 days out of the week allowing me the flexibility to help with your loving pets! I’m also free on weekends to help care for your pets during weekend trips. At a clients home, I will use the tools and toys available to care for your pets. We would go on walks and play! I will follow the clients wants for exercise and food.

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When it comes to pet care and dog walking, pet owners in Oakland, Chicago, IL trust their pets with walkers on Rover.com. Over 7915 pet owners have reviewed dog walkers in Chicago, giving them an average rating of 4.9/5. Dog walking doesn't have to be expensive. In fact, it's probably a lot more affordable than you think. You'll quickly find that there's a dog walker on Rover for just about every price range and lifestyle. Wondering how much you might expect to pay for a dog walker and pet care on Rover? Check out our average dog walking rates to get an idea before you begin a conversation with a walker who seems like a great match.

Rover is the simple, savvy way to find and book a dog walker in Oakland, Chicago, IL. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for dog owners throughout the U.S. to reach walkers who offer dog walking. Just like you, Oakland dog walkers on Rover are dog lovers too. Many of our walkers offer dog walking services and would love to take care of your dog when you can't be there. Book a 30-minute walk anytime you need it, and discover just how many of your neighbors are dog lovers too. You'll be glad to know dog walking booked on Rover is covered by the same great benefits as overnight sitting, including premium pet insurance, photo updates, and 24/7 support.

Dog Walking