House Sitting in Oakland, Chicago

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Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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1. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5 out of 4.9 stars
67 reviews
18 repeat clients
Profile image

Deven is great! He took care of Lilith for more than 3 weeks and kept us updated regularly. He sent photos and FaceTimed us, took her on walks and got her pup cups. Made our time away from our baby better and less worrisome. We definitely recommend Deven! He even stayed late on the last day cause my flight was delayed and I needed him to take care of Lilith a bit more.

Availability updated 4 days ago
Sitter Profile Image: Malcomn F.
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Sitter Profile Image: Malcomn F.
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2. Malcomn F.

Star Sitter
Kind, professional, one of the best
Washington Park, Chicago, IL, 60651
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.9 stars
33 reviews
14 repeat clients
Profile image

Malcolmn was amazing and made my trip so peaceful. He sent many pictures a day with detailed notes on their day. I really appreciate the job he’s done

Availability updated 3 days ago
Sitter Profile Image: Emily P.
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Sitter Profile Image: Emily P.
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3. Emily P.

Star Sitter
Love animals of all personalities
Chicago, IL
5.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
19 reviews
6 repeat clients
Profile image

Emily agreed to pet sit my two cats at my apartment with such short notice and over a holiday. She was beyond respectful and on top of things. She sent pictures and videos of my cats throughout my trip and made me feel totally fine leaving them with her. I was nervous to leave my cats over thanksgiving break and had never done rover before. I kept telling my parents how amazing I felt with Emily there! I will totally be calling her again.

Availability updated 16 days ago
Sitter Profile Image: Nia A.
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Sitter Profile Image: Nia A.
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4. Nia A.

Rover 101
Love 4 Love: Quality Care in Chi <3
Chicago, IL, 60639
5.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
19 reviews
12 repeat clients
Profile image

Nia was amazing with my dog, Ava. Ava is blind in one eye and can be a bit on the nervous side with new people. She took to Nia immediately. No barking or jitters at all. I knew she felt comfortable with her right away which was the ultimate endorsement! Nia followed the instructions well, sent pictures and updates during her stay and asked questions when I forgot to relay something important. She is reliable, skilled, and professional.

Availability updated 3 days ago
Sitter Profile Image: Alison F.
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Sitter Profile Image: Alison F.
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5. Alison F.

Star Sitter
Your animal's new best friend!
Near North Side, Chicago, IL, 60611
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
17 reviews
3 repeat clients
Profile image

Alison took such great care of my pup and cat while I was away! She went above and beyond to ensure everyone was comfortable, and sent the perfect number of updates. The pets were both clearly very comfortable with Alison, and we've already booked another stay for the next time I'm out of town.

Availability updated yesterday
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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6. Nicole R.

Star Sitter
Lovable reliable & trustworthy!
Bridgeport, Chicago, IL, 60616
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
18 reviews
9 repeat clients
Profile image

We moved to Chicago just a few weeks before a two week trip to Australia, so needless to say we were a bit worried about leaving our cat. I got in touch with Nicole before we even moved and she was great right from the start. Throughout our trip, she sent pictures at least twice a day and was very communicative. She asked if her boyfriend could stay with her and since we were gone for two weeks, we agreed to that. They stayed at our apartment for two weeks and treated both our cat and our apartment with care. You could barely tell anyone had stayed there when we got back. I also left them a novel of instructions and they followed it all (although I could've been more clear on how many treats he should get, he got spoiled!). As soon as she got to our house at the start of our booking, our anxieties about leaving our cat were gone. Can't recommend booking Nicole enough.

Availability updated today
Confirmed availability for Easter Weekend
Sitter Profile Image: Shakira C.
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Sitter Profile Image: Shakira C.
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7. Shakira C.

RoverGO
Rover 101
Your Pup is My Pup
South Shore, Chicago, IL, 60649
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
43 reviews
8 repeat clients
Profile image

Shakira is the absolute best and just a amazing lady! This was my first time hes I g him with a stranger. Both she and Benzo fell in love with each other and he was looking sad when she left. She took good care of my boy and kept me updated on his activities during the day. Couldn’t ask for a better experience or sitter for my puppy. Do not hesitate ti book her if she’s available; you won’t regret it I promise. She is a dog whisperer!!?

Availability updated 12 days ago
Sitter Profile Image: Malayna M.
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Sitter Profile Image: Malayna M.
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8. Malayna M.

Attentive, Active, and Kind!
Chicago, IL, 60616
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
25 reviews
6 repeat clients
Profile image

Malayna had to deal with our old dogs' issues and she did a great job. We would definitely ask her to watch them again. She also looked after my plant and I didn't ask her to.

Availability updated 36 days ago
Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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9. Danielle B.

Star Sitter
I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$100
per night
5 out of 5.0 stars
61 reviews
17 repeat clients
Profile image

Danielle did great house sitting for our two pets. She was able to connect with our new rescue, getting her to eat and not isolate herself. This was very helpful for our new rescue to get out of her shell a bit. Hoping to work with Danielle more in the future.

Availability updated yesterday
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
from
$45
per night
5 out of 5.0 stars
29 reviews
7 repeat clients
Profile image

Elizabeth took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.

Availability updated 4 days ago
Sitter Profile Image: Jade T.
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Sitter Profile Image: Jade T.
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11. Jade T.

Star Sitter
Highly experienced animal caregiver
Lower West Side, Chicago, IL, 60608
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
20 reviews
3 repeat clients
Profile image

Jade was amazing as our house sitter. Prompt, attentive, and very professional. Wouldn't hesitate to have her back to watch over our cat, and would recommend her to anyone. 😊

Availability updated yesterday
Sitter Profile Image: Brianna S.
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Sitter Profile Image: Brianna S.
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12. Brianna S.

Lover of All Things Furry!
McKinley Park, Chicago, IL, 60609
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.8 stars
19 reviews
7 repeat clients
Profile image

We’ve got one special needs dog and two elderly cats that need very specific diets and medications. We’ve also got one more dog and cat! Brianna came in at the last minute for us to take care of everyone and after getting home it’s clear how much love everyone got from her thank you so much for taking such great care of everyone and sitting for us.

Availability updated today
Confirmed availability for Easter Weekend
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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13. Emily L.

Rover 101
Pet passionate care😊🫶
Chicago, IL, 60616
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
22 reviews
2 repeat clients
Profile image

This was our first time leaving our dog with a sitter and he was in great hands with Emily. She was very communicative and went above and beyond with updates and pics. Our pup was very happy and obviously well cared for. We would definitely book again.

Availability updated yesterday
Sitter Profile Image: Alyssa G.
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Sitter Profile Image: Alyssa G.
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14. Alyssa G.

Star Sitter
I'll be the best part of their day
Near South Side, Chicago, IL, 60616
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
13 reviews
3 repeat clients
Profile image

Alyssa was great with my dog! She updated me every day with how he was and what they did that day. He seemed happy and content when I got home. She was also very respectful of my home and left it clean. I would definitely recommend her!

Availability updated 18 days ago
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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15. Emily N.

Star Sitter
Experience with multiple sized dogs
Chicago, IL, 60605
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
176 reviews
49 repeat clients
Profile image

This was our first time having Emily watch our fur babies and we couldn't be happier! She was fantastic!! Just came home to find 3 very happy pups and she also left the house and plants in amazing shape. We were gone for 10 days and received lots of great updates and pictures. We felt super comfortable leaving the pack in her care and will definitely request her again in the future. Thanks so much Emily!!

Availability updated 13 days ago
Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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16. Abi S.

Star Sitter
I’ll keep up with your pup!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
49 reviews
13 repeat clients
Profile image

Abi did a wonderful job - dogs and house were in great shape when we returned. Looking forward to having her stay again soon!

Availability updated 22 days ago
Sitter Profile Image: Connie C.
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Sitter Profile Image: Connie C.
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17. Connie C.

Responsible, attentive animal lover
Chicago, IL, 60616
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
13 reviews
4 repeat clients
Profile image

Connie was communicative and easily bonded with our dogs! She also sent pictures of them! I felt comfortable leaving my dogs with her and knew they were in good hands. Thank you for taking care of our dogs! Came back to happy puppies!

Availability updated today
Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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18. Otis B.

Dog's Best Friend
Chicago, IL, 60616
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 4.7 stars
75 reviews
32 repeat clients
Profile image

I highly recommend Otis as a Rover sitter! He was very punctual and professional during our meet and greet. During his stay in my home, he followed all instructions - including correctly using a type of leash that was new to him - and sent lots of updates and photos. I will definitely book Otis again in the future!

Availability updated yesterday
Sitter Profile Image: Sophie R.
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Sitter Profile Image: Sophie R.
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19. Sophie R.

I only sit from one home at a time
Chicago, IL, 60642
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
2 reviews

Sophie is a compassionate, dedicated, and thorough caregiver. I had the pleasure of managing her when I ran a home for women with developmental disabilities and she was excellent in her role. She has great problem-solving abilities, reliable, and communicative. I would highly recommend Sophie Ross for anyone looking for a pet caregiver. I’m extremely picky when in need for my dog and she is one of the very few people I have trusted to look after him!

Availability updated 4 days ago
Sitter Profile Image: Anais T.
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Sitter Profile Image: Anais T.
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20. Anais T.

Knowledgeable&Compassionate Sitter!
Hyde Park, Chicago, IL, 60637
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 4.7 stars
22 reviews
2 repeat clients
Profile image

Anais is the best!! My boyfriend and I went on our first long trip away from our puppy, Anais sent lots of pictures and videos every day. She was very responsible and responsive to our texts. In addition to taking great care of our puppy, she cleaned our entire apartment! Definitely recommend and will be rebooking in the future!

Availability updated 4 days ago

The median cost per night for house sitting in Oakland is $50

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  1. 1. Search

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  2. 2. Meet & Greet

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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Sitters in Oakland average 4 repeat house sitting clients

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