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

Confirmed availability: 4th of July
Anthony M.
Gentle, Flexible and Caring!Near South Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Anthony was great with our little puppy! They loved each other immediately- as soon as they met. Seeing our pup warm up to Anthony right away really helped ease… (more)

from
$18
per visit
Calendar Recently Updated
Sharon K.
2.
The Dog-Loving Law StudentLoop, Chicago, IL, 60605
Drop-In Visits, Doggy Day Care, Dog Walking

Sharon walked our pup Montgomery this evening, relatively last minute. She sent multiple photos from start to finish, and then sent a wonderful "report card" t… (more)

from
$39
per visit
Calendar Recently Updated
Aliza F.
3.
Let's Be Besties!Loop, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Aliza has been the best dog walker I have ever had! She would give my little ball of happiness water along the walks, and really developed a great bond with my … (more)

from
$17
per visit
Confirmed availability: 4th of July
Connor S.
4.
Dog and cat loverLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Connor is the best dog sitter I've ever had! I'm so grateful for her help. Not only did my dog absolutely love her but she gave her plenty of exercise and even … (more)

from
$16
per visit
Confirmed availability: 4th of July
Eileen O.
5.
South Loop Animal PalLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Super nice, will def book again! Thanks again :) (more)

from
$25
per visit
Calendar Recently Updated
6.
Fall in love with every dog I meet!Near West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

I have used Anna to watch both of my new puppies while we were away at work. She is absolutely amazing with pets, my dogs just love her! She's very reliable and… (more)

from
$30
per visit
Calendar Recently Updated
Cat + Dog Lover RNLoop, Chicago, IL, 60657
Drop-In Visits, Dog Walking

I would trust Kiersten to take care of any of my pets! She grew up with several animals in the house and she now has a wonderful cat of her own. I've seen the w… (more)

from
$17
per visit
Calendar Recently Updated
8.
Animal lover and trusted caretaker!Loop, Chicago, IL, 60605
Drop-In Visits, Dog Walking

Kelsey is a very caring pet lover. She loves her pets with her whole heart and is extremely conscientious. She has a history of building very strong bonds wit… (more)

from
$17
per visit
Confirmed availability: 4th of July
Nurturing Care Giver & Animal LoverLower West Side, CHICAGO, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Julianne is so helpful and loving with my dog and cat. She tells me how my animals are doing and my house condition everyday. Thank you so much for your help! (more)

from
$25
per visit
Confirmed availability: 4th of July
10.
Professional Dog LoverChicago, IL, 60605
Drop-In Visits, Dog Walking

Sarah is always the gal I go to when I need someone to watch my dog while I'm gone. She goes the extra mile making sure my dog Chloe is given the first-class tr… (more)

from
$17
per visit
Calendar Recently Updated
Experienced vet assistant & fosterLower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Stephanie was so great and Azul loved her! I really appreciated how she communicated with me throughout her drop in visit with Azul and made sure I knew he was … (more)

from
$20
per visit
Confirmed availability: 4th of July
12.
Friendly dog walker from the UKLoop, Chicago, IL, 60605
Drop-In Visits, Dog Walking

It was great that Jason took the time to visit with our pup before the scheduled checkins to meet beforehand and get him used to a new person. Jason provided pl… (more)

from
$15
per visit
Calendar Recently Updated
Miss my dog = decide to dog sitLoop, Chicago, IL, 60654
House Sitting, Drop-In Visits, Dog Walking

Elizabeth is caring, outgoing and responsible and would love to be a pet caregiver. She has been around dogs all her life and especially loves rescue dogs as s… (more)

from
$17
per visit
Confirmed availability: 4th of July
14.
Dog dad for hireNear West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Evan has a lot of love for dogs and I’d certainly feel very comfortable leaving my dog with him. He’s a very responsible person whom I would entrust with taking… (more)

from
$25
per visit
Confirmed availability: 4th of July
15.
Caring & Friendly Pet Lover!Lower West Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking

Sarah was amazing! She was able to confirm a last minute drop-in weekend for us. She made sure to keep us updated with pictures & messages about our cat! Defini… (more)

from
$20
per visit
Calendar Recently Updated
16.
I'll love your dog like my own!Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

I’ve known Andrea for about 6 years now. I’ve known her to be a kind, caring, and loving individual; especially to dogs. Any dog would be in amazing care with h… (more)

from
$20
per visit
Calendar Recently Updated
17.
Dogs lover and cats admirerNear South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

I found Ksenia here and am very pleased with her service. She looked after my cat Emma. Ksenia found a way to approach the difficult nature of my cat and gave … (more)

from
$20
per visit
Calendar Recently Updated
18.
No ruff times, making a pet friend.Near South Side, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Dog Walking

Angel was amazing! She took good care of my babies, always sent updates, and tidied up the litter box space! Will definitely be asking for her to take care of t… (more)

from
$17
per visit
Confirmed availability: 4th of July
19.
hi! I love animals more than peopleLoop, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

As with many pet parents I was very skeptical to have someone take care of My Maxx (Lhasa Apso) but hiring Judaea was the best decision I made for his care. M… (more)

from
$20
per visit
Confirmed availability: 4th of July
20.
BEST DOG WALKER EVER RIGHT HERENear South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Andrew would make an excellent dog sitter. He has a lot of experience taking care of our black Lab, Molly, who is now 9 years old. He takes her for walks, feeds… (more)

from
$18
per visit

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: