Dog Walking in Oakland, Chicago

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

1. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"I could not be happier with Collin. I am a new puppy owner and he has been so attentive and responsive when it comes to walking our pup twice a day. He loves... (more)"

2. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Penelope was really great with my pit mix! She was right on time, easy to talk to, and very knowledgeable. I will definitely use her again. Thanks! (more)"

3. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

5 repeat clients

"Catherine provided great service for me when I was in a bind last minute. She was very responsive, followed the instructions that I left, and most importantl... (more)"

4. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"I can attest to Sidney's abilities as a responsible and loving dog caregiver. Sidney has cared for my elderly dog, who had many health problems at the time. ... (more)"

5. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Brittany was awesome and a trooper through the bad weather. She gave great updates about my dog. Will definitely rebook with her in the future! (more)"

6. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"LeAnna was great! She established a great rapport with our dog, and he really looked forward to seeing her for walks each morning. We got great feedback abou... (more)"

7. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma is pleasant, reliable, flexible and professional. She takes great care of our fur baby and always sends updates and pictures as needed. We are so glad w... (more)"

8. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jac was extremely responsive and very quick at it too! She sent me tons of pictures of Kuma and kept me posted after every walk. Would definitely book her ag... (more)"

9. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

8 repeat clients

About: I had a dog growing up that i loved. Sam was the sweetest beagle. Back in North Carolina (where I just moved from) I used to take care of my friend... (more)

10. Mia

Best Care for Your Best Friend

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Mia is a total animal lover. I can assure you that your pet will be well taken care of under her supervision. She has lots of experience! (more)"

11. Megan

Fun, Loving Dog Owner and Lover

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

1 repeat client

About: I have a 10 year old Westie and a 3 year old Morkie. Growing up I helped care for my Golden Retriever until she was 13. I dog sit and walk for peop... (more)

12. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Dependable, great with a new dog, making all of us comfortable. (more)"

13. Maddi

Lifelong dog owner and lover :)

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Great per usual! I just love the photos! (more)"

14. Eva

Lifetime Dog Lover & Future Vet!

Kenwood, Chicago, IL, 60515

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Hi, my name is Eva, and I'm a third-year biology major with a gigantic passion for dogs! Lady is my Silky Terrier/Bichon Frise mix that I have been... (more)

15. Tom

Passionately Cheerful and Caring

Woodlawn, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Tom would be awesome with your pets! He has had cats and dogs his whole life and could be trusted to take care of them. His pets are happy when he takes them... (more)"

16. Hayley

Flexible, reliable, and available!

Bridgeport, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Hayley is an excellent caregiver! She loves animals and treats them with the utmost respect. Whether she is walking, playing, or even cleaning your furry fri... (more)"

17. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

About: Dogs & I: Over the course of my life I have raised several different dog breeds and currently still take care of my 11 year old peek-a-poo, Isabel... (more)

18. Madison

Call me the K9 crusader!

Bridgeport, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

About: I started my pet sitting career with 2 dogs name Eve and Jojo 5 years ago. As soon as I started I fell in love with these 2 babies. Thats when I kn... (more)

19. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"The best dog sitter we ever had. She was very loving to all 3 of our babies, as if they were her own. Our newest addition, is a 100 pound lap dog (at least h... (more)"

20. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

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Learn About Premier

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: