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)?

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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
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
83 reviews
36 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!

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Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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2. Saniah I.

Saniah: Your pets, my love!
Chicago, IL, 60605
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$50
per night

Arrived in time and take care of my dog perfectly, great communication all the time, definitely recommend her and super happy with the service provided.

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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3. Belicia K.

Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$50
per night

Belicia was an amazing sitter who communicated with us often. She immediately put us at ease by sending us pictures, videos, details regarding every walk, etc. When we returned to our apartment it was in the exact same condition we left it, and our two dogs, Juniper and Basil, were calm, healthy, and happy. I will definitely keep Belicia in mind for future dog sitting/walking needs.

Sitter Profile Image: Annie B.
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Sitter Profile Image: Annie B.
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4. Annie B.

Large or Small - I Love 'em All!
Loop, Chicago, IL, 60605
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
67 reviews
32 repeat clients
from
$100
per night

Annie did a great job taking care of my dog in my apartment while I was away! She left my apartment in clean condition, washed the sheets and towels as well as did any dishes she used. She sent me picture updates and always kept me in the loop. I would definitely book her again in the future!

Confirmed availability: Easter Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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5. Jasmine P.

Rover 101
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
21 repeat clients
from
$75
per night

Jasmine took outstanding care of Winston while I was gone on a work trip. She sent pictures and frequent updates while I was gone. And, followed his semi-complicated food and treat routine perfectly. I highly recommend Jasmine!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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6. Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
111 reviews
34 repeat clients
from
$55
per night

Emily did a great job staying with my dogs while I was out of town. She sent plenty of photos and my dogs were the perfect mix of happy and tired when I got back. Emily even watered my plants for me and kept my place how I left it!

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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, 60616
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
83 repeat clients
from
$70
per night

Dalila took such great care of my fur baby. This was my first time having someone watch my dog while housesitting! She sent me pictures daily, updated me constantly and left the house super clean and my dog super happy ? I will def rebook again!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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8. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
14 repeat clients
from
$88
per night

Johnathan stayed at our apartment to watch our puppy Ollie for a weekend and he was fantastic! Our puppy is fairly young and Johnathan was very patient, adaptable and accommodating to Ollie’s schedule and puppy quirks. Our puppy also has had trouble sleeping and needs medications and Johnathan successfully was able to get him to sleep throughout the night. We felt very comfortable with him with our puppy and with staying in our home. Our place was left exactly how we found it which we also appreciate. We will definitely be working with him in the future and highly recommend him!

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Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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9. Nicole C.

Responsible, reliable, WFH 🧘🏻‍♀️
Near South Side, Chicago, IL, 60616
2.0 mi. away
Boarding, House Sitting
5.0 out of 5 stars
11 reviews
from
$72
per night

Nicole took care of our house and puppy for 10 days while we were traveling. She is amazing and truly loves and cares for dogs. She communicated really well with us while we were gone but also before we were leaving. She was very flexible to accommodate our travel schedule as well. We highly recommend her and will for sure book her again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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10. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$33
per night

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 down and quickly. Once I left they sent me regular updates and I never had to worry about whether or not my kitten and dog were in good hands. I really appreciate the time and effort they put into making sure I was updated. I’ve never used Rover but I definitely will again. I also will definitely be using Levi. Thank you so much for everything!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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11. Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
54 reviews
15 repeat clients
from
$75
per night

Simply amazing. We recieved many updates, and came home to a happy and healthy dog and apartment in great condition. Would happily recommend have watch our dog again.

Confirmed availability: Easter Weekend
Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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12. Sarah S.

Rover 101
Experienced Animal Care
Bridgeport, Chicago, IL, 60609
2.0 mi. away
House Sitting
5.0 out of 5 stars
57 reviews
12 repeat clients
from
$55
per night

Sarah did a great job with Hazel and Apollo. This was the first time we have left them with a sitter (other than a family member), so we were a bit nervous, but once I asked for some updates and photos, Sarah was good about sending them! She was very prompt with her arrival times and our dogs seemed comfortable with her from the beginning.

Sitter Profile Image: Sarai O.
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Sitter Profile Image: Sarai O.
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13. Sarai O.

Reliable, trustworthy & loving!
Bridgeport, Chicago, IL, 60608
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
6 repeat clients
from
$80
per night

Sarai took great care of our apartment and of our cat, Cole! When we got back after a week-long trip away he was calm and happy. Sarai also sent us regular photos and videos and was very responsive over text. Would absolutely book again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Sateela H.
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Sitter Profile Image: Sateela H.
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14. Sateela H.

Passionate Pet Enthusiast
Chicago, IL, 60616
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night

Sateela takes great care of my dogs everytime and I can tell by how excited they are to see her each time. While they’re in her care, she sends updates, videos & pictures without me having to ask. She actually plays with them and takes them for fun walks, they love it! Sateela also helped train one of my dog and I couldn’t be more thanful

Confirmed availability: Easter Weekend
Sitter Profile Image: Thalia M.
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Sitter Profile Image: Thalia M.
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15. Thalia M.

I’d love to care 4 your little one!
Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night

I highly recommend Thalia! She cares for my dogs and she's always attentive, gentle and playful. Thalia does more than the minimum with my pets. She makes sure they're safe but she also helps keep them happy :) She has always been on time and showed up with a great attitude.

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Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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16. Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
1.8 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
20 reviews
7 repeat clients
from
$30
per night

Taylor was a great dog sitter for GiGi! She sent photos and made sure she was well taken care of. I would highly recommend Taylor for any pet sitting services!

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Sitter Profile Image: Emma & Emily F.
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Sitter Profile Image: Emma & Emily F.
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17. Emma & Emily F.

We love making new furry friends!
Hyde Park, Chicago, IL, 60615
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$50
per night

Hello , I like to tell you about Emma F. Last year my husband and I had to go away for almost 3 month, Emma stayed with our 3 pets (Jake, Luna and Misha). She did a fabulous job at taking care of them, walk them everyday and of course spoiled them. She made sure to update us often as to how our babies were doing. We highly recommend her, I assure you that your pets will be loved and taken very good care with Emma. Marcella and Don

Confirmed availability: Easter Weekend
Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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18. Masheika S.

Rover 101
All around animal lover 💜🐾
Chicago, IL, 60653
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
21 repeat clients
from
$100
per night

Masheika was so professional and cordial! She updated us with pics, messaged about any concerns, and took great care with our pups. We were so comfortable leaving our dogs in her conscientious, capable hands. We'll definitely work with Masheika again!

Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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19. Dee M.

Hyde Park Dog Lover
Grand Boulevard, Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$50
per night

Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I know she will get her exercise when she is with Dee. I cannot express enough how much I appreciate Dee & the genuine loving care she gives my little girl, Déjà. Highest recommendations from us!

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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20. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$60
per night

Abi was wonderful!! So respectful of our home and our dog was well loved while we were away!

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Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Oakland:


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