House Sitting In Near South Side Chicago

Find a loving dog sitter to watch your dog overnight in your home.

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

Search Results

Calendar Recently Updated
Sitter Profile Image: Faith L.
Verified Enhanced Background Check
Sitter Profile Image: Faith L.
Verified Enhanced Background Check
1.

Faith L.

The best care for your best friend
Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
13 reviews
2 repeat clients
from
$67
per night

Our boy is so well taken care of by Faith. She is so very patient with his special needs and understands his temperament. We appreciate the great care she takes in making sure he is comforted while we are away. Highly recommend : )

Sitter Profile Image: Munder S.
Verified Enhanced Background Check
Sitter Profile Image: Munder S.
Verified Enhanced Background Check
2.

Munder S.

Your pet needs some me time too
West Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking
5.0
109 reviews
40 repeat clients
from
$60
per night

Munder is great! We’ve booked him several times for our German shepherd puppy who is definitely a handful! Our house is always how we left it and he watches her closely so nothing in our house gets damaged. He does an amazing job with her!

Calendar Recently Updated
Sitter Profile Image: Saniah I.
Verified Enhanced Background Check
Sitter Profile Image: Saniah I.
Verified Enhanced Background Check
3.

Saniah I.

Saniah: Your pets, my love!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
8 reviews
2 repeat clients
from
$45
per night

Saniah is great! She was on time and clearly showed that she cares for animals, asking about our dog’s favorite toys and treats. I felt entirely comfortable leaving our dog with her in our home and we will be using her again!

Calendar Recently Updated
Sitter Profile Image: Otis B.
Verified Enhanced Background Check
Sitter Profile Image: Otis B.
Verified Enhanced Background Check
4.

Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
House Sitting, Drop-In Visits, Dog Walking
5.0
44 reviews
19 repeat clients
from
$55
per night

This was our second time booking Otis, the first time was from my partner’s account. Otis is reliable, responsive, and always keeps us up to date with pictures. We hired him again for a long day of house sitting because I had a long day at the office. He arrived bright and early at 7:30 and stayed until 6pm! When I had warned him that Reese was in heat, he was very kind and accepting that it was just nature. That helped reassure me that this wasn’t going to be an even more stressful situation. Otis is extremely reliable and cares deeply for the pups. He’s been able to handle our puppy and dog at the same time. Happy to continuously book him. He’s a great rover.

Calendar Recently Updated
Sitter Profile Image: tehreem g.
Verified Enhanced Background Check
Sitter Profile Image: tehreem g.
Verified Enhanced Background Check
5.

tehreem g.

All around animal lover ❤️
Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking
2 reviews
2 repeat clients
from
$55
per night

She lovessss animals the most caring person I know when it comes to animals. Super loving and always there for her pets giving them all the love in the world.

Calendar Recently Updated
Sitter Profile Image: Jasmine P.
Verified Background Check
Sitter Profile Image: Jasmine P.
Verified Background Check
6.

Jasmine P.

Rover 101
Beloved dog whisperer, is me!
Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking
5.0
42 reviews
16 repeat clients
from
$75
per night

Jasmine was amazing yet again with my dobie, Storm. I had some last minute emergency changes to my trip and her flexibility and understanding really put me at ease during a stressful time, I'm so grateful for her support! Super communicative, Jasmine took great care of my girl and my place too. Also, Storm is reactive to other dogs and I trust Jasmine to know how to deal with that. Highly recommend.

Sitter Profile Image: Misha C.
Verified Enhanced Background Check
Sitter Profile Image: Misha C.
Verified Enhanced Background Check
7.

Misha C.

Rover 101
Love All Animals!
Near North Side, Chicago, IL, 60654
House Sitting, Drop-In Visits, Dog Walking
5.0
99 reviews
43 repeat clients
from
$65
per night

Misha was great! We’re so grateful she was able to watch our dogs the weekend of our wedding. Would definitely recommend her and would book again!

Calendar Recently Updated
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check
8.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
56 reviews
30 repeat clients
from
$65
per night

Crystal responded to my cat sitting request quickly, asked great questions, followed all directions, and my kittens loved her. I will definitely try to book with her in the future!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Eileen O.
Verified Enhanced Background Check
Sitter Profile Image: Eileen O.
Verified Enhanced Background Check
9.

Eileen O.

Rover 101
South Loop Pet Pal
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
116 reviews
41 repeat clients
from
$140
per night

Eileen is always so great with Gracie! This is my 3rd time using Eileen for one of my trips. She sends regular updates and kept me informed of any issues/concerns throughout my trip. Thanks, Eileen!

Calendar Recently Updated
Sitter Profile Image: Annie B.
Verified Enhanced Background Check
Sitter Profile Image: Annie B.
Verified Enhanced Background Check
10.

Annie B.

Large or Small - I Love 'em All!
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
50 reviews
29 repeat clients
from
$100
per night

So glad to have found Annie! She was amazing with my nervous senior dog and put me at ease that he was in good hands while I was away. She was also super responsive throughout my trip and took great care of my home. I won’t hesitate to book with her again, highly recommend!

Calendar Recently Updated
Sitter Profile Image: Mary B.
Verified Enhanced Background Check
Sitter Profile Image: Mary B.
Verified Enhanced Background Check
11.

Mary B.

Active Dog Lover
Chicago, IL, 60654
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
from
$70
per night

Fantastic experience and can’t wait to get the pups together with Mary again. Highly recommend!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Emily N.
Verified Background Check
Sitter Profile Image: Emily N.
Verified Background Check
12.

Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
90 reviews
27 repeat clients
from
$50
per night

Emily was amazing! She was very accommodating with my weird flight schedule and my dogs were so happy to be with her. She also kept my home nice and tidy!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Willard Bryan K.
Verified Enhanced Background Check
Sitter Profile Image: Willard Bryan K.
Verified Enhanced Background Check
13.

Willard Bryan K.

Pet Buddy in the heart of Sloop!
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
1 repeat client
from
$80
per night

Willard was great. He clearly took wonderful care of our pup and our home. We got plenty of pictures and videos. It was our first time having Willard house sit and we would be lucky to have him back!

Calendar Recently Updated
Sitter Profile Image: Riss B.
Verified Enhanced Background Check
Sitter Profile Image: Riss B.
Verified Enhanced Background Check
14.

Riss B.

Attentive and enthusiastic care
Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
58 reviews
17 repeat clients
from
$50
per night

Riss was extremely caring, communicative, and a terrific sitter for our cats. We felt extremely comfortable leaving our cats for multiple days, and consistently received updates and photos. Riss was flexible and was great about working with our cats routine and over-excitement around feeding time. They had a great time, and would definitely have Riss sit for us again.

Calendar Recently Updated
Sitter Profile Image: Samantha H.
Verified Enhanced Background Check
Sitter Profile Image: Samantha H.
Verified Enhanced Background Check
15.

Samantha H.

Musician and Dog Lover
Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
12 repeat clients
from
$60
per night

Samantha watched our two pets while we were out of town on vacation and we couldn’t have left them in better hands. You can tell she really loves all pets as her own and she communicated regularly with us throughout our vacation. We will definitely be booking her again for when we travel!

Calendar Recently Updated
Sitter Profile Image: Dalila E.
Verified Background Check
Sitter Profile Image: Dalila E.
Verified Background Check
16.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking
5.0
179 reviews
79 repeat clients
from
$70
per night

Dalila took great care with my dog and cats (one kitten who is a naughty mess). She was flexible and helpful with meet and greet and sent updates daily while I was away. Would definitely have her over again!

Calendar Recently Updated
Sitter Profile Image: Misbah H.
Verified Enhanced Background Check
Sitter Profile Image: Misbah H.
Verified Enhanced Background Check
17.

Misbah H.

Cat-lover 😻
Chicago, IL, 60605
House Sitting, Drop-In Visits
5.0
5 reviews
from
$50
per night

Misbah took care of our cat Lunchbox while we were away on vacation in Disney world for the week and he loved her! He got lots of snuggles while we were away on vacation (he loves to be laid up in bed) and he got lots of treats and time to play with his laser light. We will definitely hire her again for future visits!

Calendar Recently Updated
Sitter Profile Image: Kathryn F.
Verified Enhanced Background Check
Sitter Profile Image: Kathryn F.
Verified Enhanced Background Check
18.

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
$45
per night

Kathryn is an exceptional dog walker with a deep understanding and love for dogs, evident from the moment you meet her. She has a unique ability to read your dog's cues and adjust her approach, ensuring your pet feels comfortable and safe. Kathryn's compassionate approach also extends to handling badly socialized dogs, which I have witnessed her expertly handle on numerous occasions. She takes the time to get to know each dog's unique personality and triggers, and is patient, gentle, and skilled in using positive reinforcement techniques to help them feel more comfortable and confident on their walks. Not only is Kathryn skilled and compassionate, but she's also incredibly reliable and responsible. She respects your home and property and keeps you updated on your pet's progress. Above all, Kathryn genuinely cares for dogs and goes above and beyond to make sure your pet is happy, healthy, and stimulated during their walks. She takes the time to play with them, give them love and attention, and clean up after them. Overall, Kathryn is the perfect choice for your furry friend. You can trust that your pet will be in the best hands possible while you're away, and you'll have peace of mind knowing they're well-cared for.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Joye E.
Verified Enhanced Background Check
Sitter Profile Image: Joye E.
Verified Enhanced Background Check
19.

Joye E.

Passionate about Pets.
Chicago, IL, 60605
Boarding, House Sitting
5.0
24 reviews
7 repeat clients
from
$65
per night

Joye is the epitome of a great dog walker, she took excellent care of my dog King. King was under Joye's care for 2 wks, she took & sent me pictures of King without me asking, she created a beautiful bond with him. My dog was in good hands like all-state.

Calendar Recently Updated
Sitter Profile Image: Jessica K.
Verified Enhanced Background Check
Sitter Profile Image: Jessica K.
Verified Enhanced Background Check
20.

Jessica K.

Caring for Your Pet Like My Own
Near South Side, Chicago, IL, 60616
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
2 reviews
1 repeat client
from
$65
per night

Highly recommend! Jessica is phenomenal. An overachiever to say the least. She makes my pets feel so, so comfortable like they're her own. It's obvious she cares for my furry children and, also, makes me feel so comfortable. I believe she is a teacher during the day, which may explain her thorough and caring nature when coming over to take care of my guys.

Search Map


The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.

House Sitting