Pet Sitting & Drop Ins In Near West Side Chicago

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

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

Search Results

Calendar Recently Updated
Autumn F.
1.
Gentle, Engaging, and Hard to FazeNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Autumn was awesome! I always give a boatload of directions for my dogs, and she was really great about it all. Plus, the first time I booked her, she really had… (more)

from
$25
per visit
Calendar Recently Updated
Justin L.
2.
Active dog lover with free timeWest Town, Chicago, IL, 60642
Drop-In Visits, Dog Walking

Justin was so friendly and communicative! He checked in on my cat and even stayed to play. Highly recommend. (more)

from
$17
per visit
Calendar Recently Updated
Monica & Calvin M.
Your fur baby's new best friends!Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Monica and Calvin are absolutely amazing. They both looked after my two shy and skittish cats with so care! I really appreciated all the detailed updates and pi… (more)

from
$20
per visit
Confirmed availability: 4th of July
Amy B.
4.
Amy 
Verified Enhanced Background Check
Home full-time, active, responsibleNear North Side, Chicago, IL, 60610
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Amy was great with my fur baby, Javi! He loved her! This was the first time I’ve had a sitter for Javi (he’s only 4 months old), so I was a little nervous. Amy… (more)

from
$27
per visit
Calendar Recently Updated
Ana Carolina A.
I take care of your buddy as my ownNear North Side, Chicago, IL, 60654
Drop-In Visits, Dog Walking

Ana goes above and beyond to give the best care to your pets! She’s helping me take care of my new pup as she grows - and the love she gives her while I’m at wo… (more)

from
$18
per visit
Calendar Recently Updated
6.
Your purfect pet sitterNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Shelby was just great! Just a pleasure to work with and she took such great care of my cat!! He was a happy guy when we got back! I would absolutely recommend S… (more)

from
$15
per visit
Calendar Recently Updated
Responsible fun dog lady!West Town, Chicago, IL, 60612
Drop-In Visits, Dog Walking

Christina has dog-sat my hyperactive pug, Jasper, on multiple occasions. Jasper can be a handful and unruly at times. However, Christina is always happy to watc… (more)

from
$30
per visit
8.
all dogs are good dogsNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

Rachel was amazing! She was very communicative and left very thorough notes and pictures. I felt great leaving my cat with her for a few days. I can’t wait to b… (more)

from
$25
per visit
Calendar Recently Updated
friendly pet care & trainingNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

Shaley is the perfect candidate to be a dog sitter because she is reliable, trustworthy, hard working, and loves dogs. She has many years of personal experience… (more)

from
$19
per visit
Confirmed availability: 4th of July
10.
Your dog will get love & attentionNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

Jade is so sweet and it’s obvious she’s an animal lover! She was available on short notice to watch our kittens for a last-minute trip, and even made time to co… (more)

from
$25
per visit
Calendar Recently Updated
11.
Chicago’s Dog Mom of the YearNear West Side, Chicago, IL, 60612
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

She’s an animal lover - especially dogs! She’s good with big and small dogs with all personality types. She’s great at supporting the training that you’ve been … (more)

from
$35
per visit
Confirmed availability: 4th of July
12.
Meet your pet’s new friendNear West Side, Chicago, IL, 60612
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

I strongly recommend Ghannam to host your dear pet. He is caring and has a no frills attitude to dog sitting. Ghannam lives in our neighborhood and we run into … (more)

from
$25
per visit
Confirmed availability: 4th of July
13.
Caring and gentle pet lover!Near West Side, Chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Sarah has been great with our puppy. It seems like she genuinely enjoys being with my dog when I receive her updates and pictures. I would 100% recommend her to… (more)

from
$25
per visit
14.
Active Dog WalkerNear West Side, Chicago, IL, 60612
Dog Boarding, Drop-In Visits, Dog Walking

About: I have grown up around dogs and volunteered at RSPCA in my hometown. I also currently have my own dog, Otis, a one-year-old puppy. Caring for Otis ha… (more)

from
$17
per visit
Calendar Recently Updated
15.
Animals live in my soulNear West Side, Chicago, IL, 60661
Drop-In Visits, Dog Walking

Elaina was an excellent sitter for our geriatric kitty. Tig’s got a lot of health issues, but Elaina took great care of him, made sure he got all of his meds, g… (more)

from
$25
per visit
Calendar Recently Updated
16.
Fun and friendly dog lover ❤️Near West Side, Chicago, IL, 60607
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Tamara was awesome. She took care of my dog while I was out of town for an entire week, dropping by the apartment 3 times a day - my pup loved it. Would recomme… (more)

from
$14
per visit
Confirmed availability: 4th of July
17.
Welcome from Bailey &ILower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care

Ariel is the true definition of a dog mom. She is very attentive and empathetic for all pets, especially her dog Bailey. She provides a safe and fun environment… (more)

from
$20
per visit
Confirmed availability: 4th of July
18.
From chihuahuas to Great DanesNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

About: I’ve had furry friends since my fury’s birthday. I’ve grown up surrounded by dogs, from chihuahuas to Great Danes to pit bulls, I’ve done it all. I’… (more)

from
$25
per visit
Calendar Recently Updated
19.
Enthusiastic Animal Lover !Near West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Izzy loves all animals ~ large and small. She has a cat, Lily, so she knows what it takes to love and care for an animal. She likes to hang out and walk our Rot… (more)

from
$26
per visit
Calendar Recently Updated
20.
Reliable, flexible, & accommodatingNear West Side, Chicago, IL, 60607
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Tina is really great with my pup, Molly! she shows a willingness to go above and beyond to put my dog's needs first and even volunteers to do extra work to care… (more)

from
$25
per visit

Rover also offers Pet Sitting & Drop Ins in:

When it comes to pet sitting, dog owners in Near West Side, Chicago, IL love Rover.com. Over 09 owners have reviewed sitters in Near West Side, Chicago, giving them an average rating of 5.0/5. The cost of pet sitting in Near West Side may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Near West Side, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Near West Side, Chicago who can provide the care your pet needs, when they need it.

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 Near West Side, 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: