Pet Sitting & Drop Ins In Near South 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

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Justin L.
1.
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
Autumn F.
2.
Gentle, Engaging, and Hard to FazeNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

autumn was professional, punctual and all around showed great attention and patience with beare. i loved the update she gave and appreciate her flexibility and … (more)

from
$25
per visit
Confirmed availability: 4th of July
Pablo V.
3.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo was great with our Pomeranian viggo , this was our first time letting someone other than our family watch him due to last minute scheduling and Pablo was … (more)

from
$17
per visit
Calendar Recently Updated
Kylie M.
4.
I’ll keep their tails waggin’ 🤗Loop, Chicago, IL, 60601
Drop-In Visits, Dog Walking

Kylie M is an outstanding pet sitter! She is a lifelong dog and cat owner. Responsible, respectful, and will treat your pets and home like her own. (more)

from
$25
per visit
Calendar Recently Updated
Makayla R.
Bountiful love and cuddles!Loop, Chicago, IL, 60601
Dog Boarding, Drop-In Visits, Dog Walking

Makayla has grown up with dogs all of her life. They are incredibly well trained and she loves them. She recently got a puppy and it's been so fun to see her lo… (more)

from
$30
per visit
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6.
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
Excited to meet your furry friends!Near South Side, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Madison is a genuine animal lover who will take amazing care of your dog. Madison is accountable, flexible, compassionate and reliable. There is no one I’d tr… (more)

from
$17
per visit
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8.
Experienced Vet Assistant :)Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

I have two small rescue dogs and Azalia is great with them. They LOVE her! She plays with them and my dogs love her attention. She is an excellent dog carer … (more)

from
$17
per visit
Calendar Recently Updated
Furry Friend’s Welcome!Loop, Chicago, IL, 60607
Drop-In Visits, Dog Walking

You know your pet is in good hands with Roz! She cares for the animal like they are her own. My dog gets so excited when Roz pulls up, he will wait by the windo… (more)

from
$17
per visit
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10.
Seasoned Pet Owner & Caregiver!Near South Side, Chicago, IL, 60605
Drop-In Visits, Dog Walking

My ladies (the cats) were very happy with Ellie. She gave awesome reports and managed to get the grumpy one to come out if her dryer (big feat in itself). (more)

from
$20
per visit
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11.
Can I pet your dog?!Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Alecia is a smart woman that is very responsible as a pet owner herself she cares deeply for animals. She has experience looking after pets and understands how… (more)

from
$21
per visit
Calendar Recently Updated
12.
Caring, Active Dog LoverNear South Side, Chicago, IL, 60616
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Dorota is extremely detailed and I think that makes for a great dog sitter. Any dog in the care of Dorota will be guaranteed to have fun and be safe. She takes … (more)

from
$19
per visit
Confirmed availability: 4th of July
13.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

I highly recommend Annie to anyone with both cats & dogs who wants their pet to be treated with care. Annie is communicative, polite, punctual, and went above a… (more)

from
$25
per visit
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14.
Loving and playful with extra timeNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Excellent. Jorie always send pictures and feedback. She is thorough and the cats like her. Appreciate that we can trust that the cats are in good hands. (more)

from
$25
per visit
Calendar Recently Updated
15.
Chicago based animal lover!Loop, chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Jenna has been a great sitter for our dog Laney. She has watched her for a couple of hours as well as an entire weekend. She has such a strong love for animals … (more)

from
$20
per visit
Confirmed availability: 4th of July
16.
Unlimited belly rubs!!!Near South Side, Chicago, IL, 60605
Drop-In Visits, Dog Walking

About: I was raised on a farm outside of Houston so my love for pets and understanding of their needs has been expanding my whole life! That being said, I h… (more)

from
$18
per visit
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Your Dog will be Treated as Family!Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Josh and I have been friends for over three years. This past year he got his first puppy, a golden doodle. Between constantly educating himself and being a grea… (more)

from
$15
per visit
Calendar Recently Updated
18.
Zoe 
Verified Enhanced Background Check
Hello. My name is Zoe Kinser.Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Zoe was great. My cats, who often are iffy with strangers, really liked her. She’s communicative, replies quickly, sent photos everyday and some videos. I would… (more)

from
$16
per visit
Confirmed availability: 4th of July
Home full time - loves dogs!!Loop, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care

Prapatsorn has been an absolute blessing! She is prompt, reliable, trustworthy and will update me when I’m out of town which is always comforting. I’ve always… (more)

from
$25
per visit
Calendar Recently Updated
20.
Trustworthy and always punctualNear South Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Lais is a great person. She is very responsible, communicative, flexible and easy to work. Your dog will love to spend a time with her. (more)

from
$17
per visit

Rover also offers Pet Sitting & Drop Ins in:

Dog owners in Near South Side, Chicago, IL love booking pet sitting with sitters on Rover.com. Over 7,915 pet owners have reviewed pet sitters in Chicago, giving them an average rating of 4.9/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Near South Side, Chicago.

Rover.com is the simple, savvy way to find and book Near South Side, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Near South Side, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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 South Side, Chicago, 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: