House Sitting in Oakland, 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

Sitter Profile Image: Shakira C.
Sitter Profile Image: Shakira C.
Your Pup is My Pup
South Shore, Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking

Shakira and Bo had a wonderful time whilst I was off celebrating the marriage of my son with family and friends. I received pics and messages that took the worr… (more)

from

$75

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Dalila E.
Sitter Profile Image: Dalila E.
2.
PET SPECIALIST
Chicago, IL, 60609
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

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 … (more)

from

$58

per night
Calendar Recently Updated
Sitter Profile Image: Susan C.
Sitter Profile Image: Susan C.
3.
You're Dog is My Dog!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Truly the best dog sitter I’ve ever had, both on Rover and personally. I trust her implicitly and she treats my two “children” like her own. I never worry when … (more)

from

$60

per night
Calendar Recently Updated
Sitter Profile Image: Molly S.
Sitter Profile Image: Molly S.
4.
Openly Available Animal Caretaker
Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Molly is so wonderful with my pets, and they just love her. She has cared for my pets many times, and she is always kind, gentle, and loving. She goes above and… (more)

from

$30

per night
Calendar Recently Updated
Sitter Profile Image: Lindsay J.
Sitter Profile Image: Lindsay J.
Cat mom and animal lover
Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking

Lindsay was great we needed a very last minute sitter, and she was able to make a miracle happen. Our dog has separation anxiety, and he was completely at ease … (more)

from

$63

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Niesha D.
Sitter Profile Image: Niesha D.
6.
Fur-babies love me!
Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Dog Walking

Niesha is incredibly responsible. She works with my at BUST and I can always rely on her. She also looooves animals of all kinds. Thanks (more)

from

$38

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Belicia K.
Sitter Profile Image: Belicia K.
Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Belicia is wonderful! I felt so comfortable leaving my girl with her. She’s so communicative and thoughtful, I can’t wait to work with her again! (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Sarah S.
Sitter Profile Image: Sarah S.
8.
Experienced Animal Care
Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking

Sarah has watched our dogs twice nice for an extended weekend both times. She arrives promptly, is neat and tidy when in our home and she always treats our dogs… (more)

from

$55

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Naimah B.
Sitter Profile Image: Naimah B.
9.
Experienced Dog Lover
Near South Side, Chicago, IL, 60616
House Sitting

Nai really came through for me and was able to provide a calm and caring environment for my Layla when Southwest flights caused holiday chaos! Nai was patient w… (more)

from

$75

per night
Calendar Recently Updated
Sitter Profile Image: Munder S.
Sitter Profile Image: Munder S.
10.
Your pet needs some me time too
West Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking

Munder was great with my cat Cassidy! I really appreciated the daily updates, photos & videos, and how clean my apartment was when I returned home. Cassidy was … (more)

from

$60

per night
Calendar Recently Updated
Sitter Profile Image: Kayla S.
Sitter Profile Image: Kayla S.
11.
Ready for four-legged love again <3
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking

About: Hello my name is Kayla, I am so excited to meet you and your furry children! I am a passionate animal lover that grew up with dogs in her home, caring for up to… (more)

from

$32

per night
Calendar Recently Updated
Sitter Profile Image: Erin M.
Sitter Profile Image: Erin M.
12.
Reliable care for your pet
Bridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Thank you so much for caring for our pets! (more)

from

$40

per night
Calendar Recently Updated
Sitter Profile Image: Pablo V.
Sitter Profile Image: Pablo V.
13.
Fun walks
Near West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo was absolutely amazing. Our pups are rescue dogs, and one has high anxiety. However, Pablo made them both feel so comfortable and gave them plenty of exer… (more)

from

$59

per night
Calendar Recently Updated
Sitter Profile Image: Nasla G.
Sitter Profile Image: Nasla G.
14.
I love your pet as my own!
Chicago, IL, 60607
Boarding, House Sitting, Drop-In Visits, Dog Walking

Nasla took wonderful care of my challenging pup, Rufus. She sincerely enjoyed his company, was very responsive and professional, and sent plenty of pics to this… (more)

from

$100

per night
Calendar Recently Updated
Sitter Profile Image: Elizabeth D.
Sitter Profile Image: Elizabeth D.
Does your pet need a new friend?
Douglas, Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking

They were AWESOME! Immediately we hit it off talking about our mutual interests. My dog gets a bit hyper but Levi was able to demonstrate techniques to calm him… (more)

from

$25

per night
Calendar Recently Updated
Sitter Profile Image: Madeline S.
Sitter Profile Image: Madeline S.
Experienced Vet Assistant- Meds ok!
Chicago, IL, 60654
House Sitting, Drop-In Visits, Dog Walking

Madeline is amazing, I highly recommend her. My cats loved her immediately and she was great with providing updates. One of my cats has asthma and needs a daily… (more)

from

$70

per night
Calendar Recently Updated
Sitter Profile Image: Emily N.
Sitter Profile Image: Emily N.
17.
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emily was amazing and I appreciated the extra things she did with Milo! She gave me updates and pictures! She will be my regular house sitter for Milo now!!!! T… (more)

from

$40

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Shironda S.
Sitter Profile Image: Shironda S.
Passionate about people and pets
South Shore, Chicago, IL, 60649
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
15 years of experience

About: I love people and pets. I had the good fortune to grow up having beloved furry family members. I always keep my best friend's dogs when she has to t… (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Alysia G.
Sitter Profile Image: Alysia G.
19.
Reliable, non-smoking pet lover
Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Alysia was great with our dog! Very communicative, followed all instructions and really friendly. We’ll definitely book with her again! (more)

from

$55

per night
Calendar Recently Updated
Sitter Profile Image: Roxanne H.
Sitter Profile Image: Roxanne H.
20.
Cat lover, petter, sitter for hire
Chicago, IL, 60605
House Sitting, Drop-In Visits

Thank you Roxanne for taking such good care of the boys! They were very relaxed and happy when we returned home! (more)

from

$45

per night

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