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.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
37 reviews
13 repeat clients
from
$20
per visit

Crystal is a really thoughtful and observant sitter that really tended to our cat, Taraji’s needs. Her experience with animals showed in her care and we can’t recommend her enough. We’re deeply appreciative of her services!

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Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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2.

David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
48 reviews
18 repeat clients
from
$20
per visit

David took great care of our kitty for a weekend of drop-in visits! Super responsive, very detailed updates with photos, and overall great communication.

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Sitter Profile Image: Emily O.
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Sitter Profile Image: Emily O.
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3.

Emily O.

Emily O- pet lover forever!
Loop, Chicago, IL, 60605
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
3 repeat clients
from
$26
per visit

Emily was amazing looking after my dog on such short notice! She was great in communicating with me while I was away and made sure my sweet pup was well looked after. I Ioved receiving lots of updates with pictures and videos! I will definitely be contacting Emily next time I need someone to take care of my dog!

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Sitter Profile Image: Shayda S.
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Sitter Profile Image: Shayda S.
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4.

Shayda S.

Nurturing & protective dog lover
Loop, Chicago, IL, 60604
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
4 reviews
from
$17
per visit

Shayda was amazing! She was so warm and full of love with Daisy! She also updated me with pics on how my dog was doing during the stay. Shayda just made me feel very comfortable trusting her right away. I would 100% recommend using her!!

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Sitter Profile Image: Leanna P.
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Sitter Profile Image: Leanna P.
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5.

Leanna P.

Reliable, Vigilant, and Caring!
Loop, Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
14 reviews
6 repeat clients
from
$22
per visit

Leanna was amazing, caring, and communicative, which is everything you could ask for from someone on Rover. She not only responded quickly to our last minute request for check-in’s but also was incredibly flexible and communicative when our lockbox was stuck, and the locksmith had to drive down to our home and literally saw it open. I also have a cat who just had surgery and Leanna was attentive to his post-op needs. Pretty much every complication in the book she handled with kindness and communication. Immense thanks to Leanna! Book her!

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Sitter Profile Image: Yauheniya L.
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Sitter Profile Image: Yauheniya L.
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6.

Yauheniya L.

Loving Pet Sitter, Work from Home
Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
34 reviews
15 repeat clients
from
$27
per visit

Yauheniya was the best friend for Luis, my 10 year old Yorkie! She walked 3 times a day, fed on time and played with him. She is very nice and was always on time, and reachable over phone. Luis adored her! And I knew that he was safe and I could enjoy my vacation. I would definetely recommend Yauheniya!

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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7.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
161 reviews
72 repeat clients
from
$24
per visit

Dalila was great! This was my first time using this service and she was very patient with helping me navigating the app. She was timely and kept me inform with what’s going on. I will definitely be using her again.

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Sitter Profile Image: Luis G.
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Sitter Profile Image: Luis G.
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8.

Luis G.

Here to make DOGS feel like DAWGS!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$20
per visit

Luis has a great love for animals! He is exceptionally knowledgeable about proper care and training for dogs as well as cats. His work raising his own dog shows his dedication and nurturing nature that a pet needs to be happy.

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Sitter Profile Image: Judy L.
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Sitter Profile Image: Judy L.
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9.

Judy L.

Pawsitive Progress: Walk & Train
Chicago, IL, 60616
Drop-In Visits, Dog Walking
3 reviews
from
$20
per visit

Judy is an incredible trainer. She trained my two dogs. They were a pleasure to have after her training. I highly recommend her. She addressed every problem with professionalism

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Sitter Profile Image: Alexandra M.
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Sitter Profile Image: Alexandra M.
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10.

Alexandra M.

Rover 101
Experienced 🐱sitter in South Loop!
Near South Side, Chicago, IL, 60605
Drop-In Visits
5.0
13 reviews
6 repeat clients
from
$20
per visit

Alexandra took great care of my kitties! She made sure they got their medicines and plenty of play time and cuddles. She’s was very understanding of my last minute schedule changes as well. I will definitely hire her again for pet sitting!

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Sitter Profile Image: Sylvia W.
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Sitter Profile Image: Sylvia W.
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11.

Sylvia W.

Flexible Schedule, cats and dogs!
Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
1 review
1 repeat client
from
$17
per visit

About: I am dedicated to precision and care in Dog Walking and Pet sitting. I have two cats and grew up with pets. I understand how important it is to have someone you trust and who follows your care instructions. I'm currently a student so I have a flexile schedule. I am available for most weekdays and weekends. I can accommodate schedule changes easily and am almost always in the area. I ensure my cats' well-being by providing them with high-quality, balanced meals tailored to their specific dietary needs. I create a stimulating environment by offering toys and engaging playtime to keep them mentally and physically active. Regular veterinary check-ups and grooming sessions are essential to maintain their health and appearance.

Sitter Profile Image: Jason C.
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Sitter Profile Image: Jason C.
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12.

Jason C.

Friendly dog walker from the UK
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
69 reviews
25 repeat clients
from
$18
per visit

Jason is such a responsive and wonderful dog walker! He is so kind to my three very particular pups (one of which is blind and one is a shy foster). I feel so comfortable and happy knowing they are in great care! Highly recommend!

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Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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13.

Shimmy G.

I love my pups & I’ll love yours!
Near South Side, Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
50 reviews
13 repeat clients
from
$20
per visit

I highly recommend Shimmy as a responsible pet caregiver. I’ve personally watched the way she has cared for her pets over the last 20yrs and it’s been the equivalent of caring for a family member you love dearly. Having watched her adopt her second dog and give him the life he deserves, could have potentially saved his life. It required a level of skill, energy, and patience that not everyone is equipped with. She has it! Your pets will no doubt be in great hands!

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Sitter Profile Image: Chloe M.
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Sitter Profile Image: Chloe M.
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14.

Chloe M.

Flexible schedule to fit all pets!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
2 reviews
from
$14
per visit

Chloe is one of the most caring people I know. Her compassion is not only for people, but for animals as well. She has a guinea pig, Maggie, who she absolutely adores. Maggie is consistently well taken care of, and Chloe is always paying full attention to her and attending to any needs she may have. Chloe is responsible, reliable, and kind, and is a genuinely good person, who loves, cherishes, and respects all animals.

Sitter Profile Image: Manasa & Andy B.
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Sitter Profile Image: Manasa & Andy B.
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15.

Manasa & Andy B.

Husband/wife duo who loves animals!
Near South Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking
1 review
from
$17
per visit

Manasa is a sweet and gentle person who treats all animals and humans with care and empathy. She would make an excellent caregiver for the beloved furry friends of others.

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Sitter Profile Image: Kathryn F.
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Sitter Profile Image: Kathryn F.
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16.

Kathryn F.

A fun, reliable human for every 🐶
Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
1 repeat client
from
$15
per visit

Kathryn was excellent in her care of Finn. She was a great communicator, giving me detailed reports of her check ins and how he was doing. He’s got a lot of quirks and I felt confident in her abilities to handle them. Definitely recommend her service. Will be booking her again for future travel.

Sitter Profile Image: Samantha H.
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Sitter Profile Image: Samantha H.
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17.

Samantha H.

Musician and Dog Lover
Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
32 reviews
12 repeat clients
from
$20
per visit

Samantha did drop-in visits for my two cats for five days. She did a great job. Sarah was communicative and followed directions and the cats like her. I would hire her again.

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Sitter Profile Image: Anthony M.
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Sitter Profile Image: Anthony M.
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18.

Anthony M.

Gentle, Flexible and Caring!
Near South Side, Chicago, IL, 60616
Drop-In Visits, Dog Walking
5.0
140 reviews
40 repeat clients
from
$18
per visit

Anthony had a calm approach with our dogs … which was important to us. They are “new” to the city life … so we always wonder what might trigger them. And if a “new” person walking them would make them act differently. Anthony even paid attention to the details like a special lock we have on the door. And fed our pups treats at the end. It was a good experience.

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Sitter Profile Image: Julian K.
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Sitter Profile Image: Julian K.
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19.

Julian K.

Seasoned sitter who loves animals!
Chicago, IL, 60605
Drop-In Visits, Dog Walking
5.0
8 reviews
3 repeat clients
from
$15
per visit

Julian was awesome! He was available when I was leaving town pretty last minute, made it easy to organize with him, and made it really easy to feel comfortable that Waldo would have plenty of care and attention! He sent great pictures and, my sometimes shy kitty, was happily playing immediately!

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Sitter Profile Image: Michelle B.
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Sitter Profile Image: Michelle B.
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20.

Michelle B.

Active Walker and Loving Pet Sitter
Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$15
per visit

Michelle is an excellent dog trainer and walker! In the past, she has helped train my dog and implement loose leash walking using a variety of leashes and harness combinations. She also uses reward driven training via treats which works great with food driven dogs.

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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:

Drop-In Visits