Pet Setting & Drop Ins in Kenwood, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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Drop-In Visits

How large is your dog (in lbs)?
$10
$150
Confirmed availability
Thanksgiving
1. Kat

Recent grad who LOVES DOGS

Kenwood, Chicago, IL, 60615

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

1 repeat client
11 reviews

About: None (more)

from
$20
per visit
Calendar Recently Updated
2. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

17 repeat clients
24 reviews

"Karolina has sat and done walks for me 3 times. She is very responsive and sends followup messages to let me know how things are going. Will definitely wor... (more)"

from
$15
per visit
Calendar Recently Updated
3. Katja

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients
6 reviews

"Very professional and friendly. I have a puppy and it’s good that she knew her stuff and was accommodating! Much appreciated! (more)"

from
$20
per visit
Confirmed availability
Thanksgiving
4. Sam

Basically Raised by Dogs.

Bridgeport, CHICAGO, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

6 reviews

"Sam without a doubt has one of the best ways with dogs! I have a 170 Mastiff and Sam is amazing with him. He is just a natural and all dogs just love him.... (more)"

from
$18
per visit
Calendar Recently Updated
5. Elisa

love dogs!

New City, Chicago, IL, 60609

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

1 repeat client
2 reviews

"Elisa has been a very good inspirational person when it came down to adopting animals and care taking. She shows a lot of passion towards any kind of animal ... (more)"

from
$16
per visit
Calendar Recently Updated
6. Sarah

Grad student seeking furry friends

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 review

"Sarah is a responsible person who grew up with both large and small dogs and she has always given them the best care. I can guarantee your dog will receive l... (more)"

from
$16
per visit
Calendar Recently Updated
7. Megan

Last minute bookings available!

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients
11 reviews

"Megan did such a great job. I had to leave without getting to go home to check on my cats and Megan figured everything out easily and made it stress free. Sh... (more)"

from
$12
per visit
8. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

1 repeat client
8 reviews

"Jennifer was great to communicate with! We will be asking her to drop-in in the future. (more)"

from
$16
per visit
Calendar Recently Updated
9. Arielle

Student who needs a dog in her life

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

1 repeat client
7 reviews

"I can highly recommend Arielle as a caregiver for dogs. She took care of my 8 year old Cockapoo while I was away, and he seemed plenty calm and happy when I ... (more)"

from
$16
per visit
Calendar Recently Updated
10. Nicole

Experienced Part-Time Dog Walker!

Hyde Park, Chicago, IL, 60637

Drop-In Visits, Dog Walking

2 repeat clients
2 reviews

"Nikki watched my cats while I was away one weekend, and I can honestly say that I didn't worry about them one bit in her care. One of my cats is a very senio... (more)"

from
$16
per visit
Calendar Recently Updated
11. Zak

Home all day - fenced yard

Douglas, Chicago, IL, 60616

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

No Reviews Yet

About: None (more)

from
$16
per visit
Calendar Recently Updated
12. Samaree

Free spirited dog lover!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 review

"Samaree is such a animal lover. She is caring and enjoys being around all animals, especially dogs. I’ve witnessed her be a great dog mommie and a wonderful ... (more)"

from
$16
per visit
Calendar Recently Updated
13. Madeleine

I can’t wait to love your dog too!

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

3 reviews

"Madeleine is a kind, gentle and caring soul and recognizes the best in our pets. She has love to share with all. She is also a hard working and disciplined... (more)"

from
$16
per visit
Calendar Recently Updated
14. Maddy

Will play and pet nonstop

Woodlawn, Chicago, IL, 60637

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

1 review

"Choose Maddy! She has been a loving and thoughtful dog owner for six years now. Maddy is very responsible and can be trusted with your pets and in your hom... (more)"

from
$16
per visit
15. Zachary

Zach's Hyde Park Dog-Care

South Side, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

2 reviews

"Zach has offered wonderful assistance to our family. He is very easy to work with and responsible with our 4 legged baby. Even when we've had foster dogs, Za... (more)"

from
$20
per visit
Calendar Recently Updated
16. Morgan

Time for long walks - dog lover

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 review

About: None (more)

from
$20
per visit
Calendar Recently Updated
17. Bob

Bob's Boarding in Hyde Park

South Side, Chicago, IL, 60615

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

14 repeat clients
27 reviews

About: None (more)

from
$22
per visit
18. Katlyn

Consistent & Loving :)

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients
9 reviews

"Excellent sitter for my two cats!! (more)"

from
$18
per visit
Calendar Recently Updated
19. Kyle

Flexible hours - love walking dogs!

Hyde Park, Chicago, IL, 60615

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

1 review

"If it weren't for his travel schedule, Kyle would have a dog of his own. He absolutely loves dogs. Any dog that stays with Kyle is sure to get plenty of ... (more)"

from
$16
per visit
Calendar Recently Updated
20. Grace

Caring evening/weekend sitter!

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

3 reviews

"Grace was amazing - she offered to come meet me and the dogs beforehand for care instructions and was super flexible with the time she came over. She sent ph... (more)"

from
$18
per visit

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Kenwood, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Kenwood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Kenwood, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Kenwood pet sitters and avoid the kennel.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 sitters in Kenwood, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter 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:

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