Dog Walking in Oakland, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Laura V.
1.
✨ Life is better with pets ✨Lower West Side, Chicago, IL, 60608
Drop-In Visits, Dog Walking

Laura has a love for pets that is unmatched. I often joke with her by saying that she cares more for my dogs than she does for me lol. Anyone interested in hiri… (more)

from
$20
per walk
Calendar Recently Updated
Susan C.
2.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan is quick to respond. She was very attentive and caring with my dog, and sent frequent updates and messages. Overall very satisfied with no complaints. (more)

from
$20
per walk
Calendar Recently Updated
Angel D.
3.
No ruff times, making a pet friend.Near South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Angel has both walked and watched my dogs when I am out of town. She is communicative, professional and does so well with both of my pups. She is my go to anyti… (more)

from
$20
per walk
Confirmed availability: Memorial Day
Lorraine C.
Always had animals in my lifeLoop, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

So happy with my cat sitter Lorraine, she is always so happy to see him and shows him her toys and cuddles up with him before a walk. She is very detailed with … (more)

from
$20
per walk
Calendar Recently Updated
Seven B.
5.
Pet lover ready to make new pals!Lower West Side, Chicago, IL, 60616
Drop-In Visits, Doggy Day Care, Dog Walking

I have seen Seven display immense care for the animals in their care on numerous occasions. They truly do go above and beyond in making sure the animals needs a… (more)

from
$14
per walk
Calendar Recently Updated
6.
Loves animals— detail oriented!Kenwood, Chicago, IL, 60615
Drop-In Visits, Dog Walking

For a last minute booking, Tracie really came through for us! Misty loved her! Thanks again for your wonderful services! ? (more)

from
$25
per walk
Calendar Recently Updated
7.
Experienced w/ Pets & TrustworthyLower West Side, Chicago, IL, 60608
Dog Walking
10 years of experience

About: I’ve always had at least one dog in my household since I was born. My family is full of animal lovers so I’ve experienced everything from living with… (more)

from
$20
per walk
Confirmed availability: Memorial Day
8.
Energetic sitterNear West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
6 years of experience

About: I’ve had a love of animals for as long as I can remember. I love being outside and doing my daily walks in the neighborhood. I’m currently available… (more)

from
$20
per walk
9.
Long-time pet lover and caretakerLower West Side, Chicago, IL, 60608
Dog Walking

Maya is the best! So attentive to my Peppers’ needs. I always come home to a happy girl! (more)

from
$26
per walk
Experienced dog handlerBridgeport, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Jennifer is definitely an experienced and capable dog caretaker! She was super friendly, punctual, available, and took great care of our boy. We would not hesit… (more)

from
$25
per walk
11.
Your dog's new best friend!Douglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
10 years of experience

About: In my neighborhood back home, I was the resident dog/house/baby-sitter for several years, especially as I got into high school and had more independe… (more)

from
$20
per walk
Confirmed availability: Memorial Day
12.
Caring and Reliable Pet CareBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Natalia was amazing! She is a pleasure to work with and my dogs loved her so much. I am booking her again for next weekend! (more)

from
$40
per walk
Calendar Recently Updated
13.
Reliable routine Queen for your petBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

As someone who has known Erin since she was young, I've always known her as someone who loves animals. When getting into her first apartment – she immediately t… (more)

from
$15
per walk
14.
Fun doggo day care services.Woodlawn, Chicago, IL, 60637
Dog Walking
10 years of experience

About: We have 2 dogs of our own and they enjoy hanging out in our yard and going on long walks in the woods. They would love to make new friends and can jo… (more)

from
$20
per walk
Confirmed availability: Memorial Day
15.
Dogs are SUPER HEROSKenwood, Chicago, IL, 60653
Dog Walking
1 years of experience

About: During the pandemic I used to take my friend 1 year pitbull name Thor for walks 4 days out of the week for 11 months. Pet care definitely fits into … (more)

from
$20
per walk
Confirmed availability: Memorial Day
All Creatures, Great and SmallHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

I wrote this above, but really, Rane was a godsend while my friend was recovering from the hospital. 100% easy communication and reliability. If you're reading … (more)

from
$30
per walk
Calendar Recently Updated
17.
Caring, energetic, and trustworthy!Hyde Park, Chicago, IL, 60615
Dog Walking

Hands down the kindest, most reliable, friendliest, and caring dog walker imaginable. 10/10 would recommend for any service. (more)

from
$20
per walk
Confirmed availability: Memorial Day
18.
Dogs really like meDouglas, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Preston is wonderful! He communicates well and gives my dog extra time when he can. Treats my dog very well and tries to take him on the most nature-y walks for… (more)

from
$25
per walk
Confirmed availability: Memorial Day
Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

My dog, Kira, is a high maintenance dog due to her excessive energy and anxiety. Since Kira and Masheika have met she goes beyond just caring for her simple nee… (more)

from
$28
per walk
Calendar Recently Updated
20.
Make every dog feel welcomed!Douglas, Chicago, IL, 60616
Drop-In Visits, Dog Walking
1 years of experience

About: I was in middle school when I adopted a pet Beagle. We watched shows together, went on walks and had the best time training him. I’m happy when I spe… (more)

from
$25
per walk

When it comes to pet care and dog walking, pet owners in Oakland, Chicago, IL trust their pets with walkers on Rover.com. Over 7,915 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.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover walkers in Oakland, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a walker who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including: