House Sitting in Kenwood, Chicago

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Sitter Profile Image: Emily P.
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Sitter Profile Image: Emily P.
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1. Emily P.

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

Emily has sat for my cat multiple times and is always on time and easy to reach! He warmed up to her right away and I felt at ease during my trip knowing she was there. Will definitely be booking with her again!

Availability updated 22 days ago
Sitter Profile Image: Alison F.
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Sitter Profile Image: Alison F.
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2. Alison F.

Star Sitter
Your animal's new best friend!
Near North Side, Chicago, IL, 60611
5.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5 out of 5.0 stars
24 reviews
6 repeat clients
Profile image

Alison is amazing. She absolutely loves animals and my dog took to her right away. During my travels my dog did not want to leave her side! This is as comfortable as I have ever felt leaving my little one with a sitter. I will be using her exclusively going forward. She is exactly what we all look for when searching for a good sitter. 10/10

Availability updated 4 days ago
Sitter Profile Image: Anna O.
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Sitter Profile Image: Anna O.
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3. Anna O.

Like you never left: care & safety♥
Chicago, IL, 60616
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
4 reviews

We have used Jackson and Anya many times to take care of our pups and our house. What I appreciate about them is the ease of communication. We travel quite a bit, and it's nice receiving regular updates and photos from them about how things are going. We always find the house clean, plants alive and watered, and the pups happy when we return. Highly recommend.

Availability updated 7 days ago
Sitter Profile Image: Zachary S.
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Sitter Profile Image: Zachary S.
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4. Zachary S.

Star Sitter
Recent grad and animal lover
Lower West Side, Chicago, IL, 60608
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
16 reviews
3 repeat clients
Profile image

Zachary went above and beyond from organizing a meet and greet before pet sitting to ensuring my house was clean when I came home. He took great care of my dog and I wouldn’t hesitate to leave him with Zachary again.

Availability updated 11 days ago
Sitter Profile Image: Brianna S.
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Sitter Profile Image: Brianna S.
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5. Brianna S.

Lover of All Things Furry!
McKinley Park, Chicago, IL, 60609
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.8 stars
20 reviews
8 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 3 days ago
Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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6. Otis B.

Dog's Best Friend
Chicago, IL, 60616
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 4.6 stars
75 reviews
32 repeat clients
Profile image

After a seven night stay, we couldn’t be happier! The dogs seemed happy, we got photos / communication every day, and the house was even left clean. We would use again / recommend to anyone!

Availability updated 9 days ago
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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7. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.9 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 was so great! We were able to meet before the house sitting and went over the specifics of my dog. She gave me daily updates and let me know he was doing well which I really appreciated!! I would definitely book again ?

Availability updated 3 days ago
Sitter Profile Image: Michael C.
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Sitter Profile Image: Michael C.
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8. Michael C.

Rover 101
Special Needs & Senior Specialist
Hyde Park, Chicago, IL, 60615
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$43
per night
5 out of 5.0 stars
36 reviews
18 repeat clients
Profile image

Michael stayed with our boy Wrigley for a long weekend and was so wonderful to work with. Our dog is an older boy and needs some special considerations. Michael was so attentive and responsive to Wrigley's special needs. He was also very communicative with us during the stay. I highly recommend Michael as a sitter!

Availability updated 3 days ago
Sitter Profile Image: Malcomn F.
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Sitter Profile Image: Malcomn F.
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9. Malcomn F.

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

We had an excellent experience with Malcomn while visiting Chicago! He took amazing care of our two large dogs, keeping them happy, exercised, and loved while we were away. I highly recommend him for anyone looking for a trustworthy and attentive pet sitter!

Availability updated today
Confirmed availability for 4th of July Weekend
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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10. Nicole R.

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

Nicole was wonderful! She messaged me everyday on how my dog and cat were doing with pictures or videos. She stayed for like 10 days in our home with them so we are very grateful!

Availability updated today
Sitter Profile Image: Anais T.
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Sitter Profile Image: Anais T.
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11. Anais T.

Knowledgeable&Compassionate Sitter!
Chicago, IL, 60637
1.2 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 was very communicative - she sent lots of pictures. She kept the place clean and was respectful. I would book her again. She was accommodating with special needs of my dog.

Availability updated today
Sitter Profile Image: Connie C.
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Sitter Profile Image: Connie C.
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12. Connie C.

Responsible, attentive animal lover
Chicago, IL, 60616
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
14 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 23 days ago
Sitter Profile Image: Brianna J.
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Sitter Profile Image: Brianna J.
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13. Brianna J.

Expert belly rubber & bum scratcher
Grand Boulevard, Chicago, IL, 60653
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
Profile image

Bre was fantastic watching our Cat! He has some medical that require extra effort/ needs and Bre followed directions and was very communicative in times of doubt. She also took great care of our house. We will hire her again and highly recommend her to watch your pets!

Availability updated 10 days ago
Sitter Profile Image: Samantha E.
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Sitter Profile Image: Samantha E.
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14. Samantha E.

Star Sitter
Professional Pet Sitter & Pup Lover
Hyde Park, chicago, IL, 60615
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
96 reviews
50 repeat clients
Profile image

Samantha was great! She really saved us when we were put in a bind by a last minute cancellation by another sitter. She sent us daily updates and pictures of our pups, and endured their puppy energy. We came home to a clean house and happy puppies. We would definitely book Samantha again!

Availability updated yesterday
Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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15. Abi S.

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

Abi was great with our pups! They were calm and happy when we got back from our trip, and the house was in great shape. Looking forward to the next time.

Availability updated yesterday
Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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16. Dee M.

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

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!

Availability updated 7 days ago
Sitter Profile Image: Carlie R.
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Sitter Profile Image: Carlie R.
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17. Carlie R.

Red Rover (x2) Send Carlie On Over!
Woodlawn, Chicago, IL, 60637
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
8 reviews
2 repeat clients
Profile image

We had the best experience with Carlie! Her and Ani (her pup) stayed at our house for the week while we were on a family trip. Our boy Leo is a Great Dane and she was amazing with him. Not everyone can handle big dogs. I felt at ease with Carlie at our home. I got frequent updates and pictures too! The house was well maintained and in the condition we left it in. 5+ ⭐⭐⭐⭐⭐✨

Availability updated 2 days ago
Sitter Profile Image: Molly G.
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Sitter Profile Image: Molly G.
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18. Molly G.

Reliable, friendly, and caring!
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per night
3 reviews

Molly has always loved and adored animals. As an adult she cared lovingly for two senior cats with health complications, (one was her own), as well as provided pet sitting for many animals, including a family with two cats and one large dog. This family continues to share with me how much they cherish and appreciate Molly’s time with their pets. Regularly walking dogs is something Molly is dedicated to and enjoys! Molly is highly responsible, trustworthy, reliable and is very caring. She also is creative in her thinking as well as problem solving. These are characteristics which help in working with pets where common issues arise. Molly has a natural gift of being intuitive and empathic towards people and animals, she excels in communication, and she is invested in health and safety. For these reasons, animals often feel safe with her, and they are extremely happy to see her. Animals are also often calm in her presence and thoroughly enjoy her company. As an owner of a pet, you will appreciate Molly’s skills, too. Molly talks with animals reassuringly and after getting to know them, she can read non verbal cueing. When it comes to Molly and animals, they are mutually drawn to each other. It is with great enthusiasm that I highly recommend Molly for pet sitting.

Availability updated today
Sitter Profile Image: Daniel K.
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Sitter Profile Image: Daniel K.
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19. Daniel K.

Pet Care Professional at a Discount
Chicago, IL, 60615
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
11 reviews
2 repeat clients
Profile image

Daniel has done an amazing job working with our furry friends. Our dog has lots of special needs and Daniel handles them all without any stress or worry!

Availability updated 22 days ago
Sitter Profile Image: Mia L.
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Sitter Profile Image: Mia L.
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20. Mia L.

Pet Enthusiast and Animal Care
Hyde Park, Chicago, IL, 60615
0.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
4 reviews

Mia has watched my two cats many times -- each time she has been SO caring and attentive. My cats are picky eaters, and she took extra care when making sure they were fed. She went above and beyond with playing with them and keeping them company while I was gone. She kept me up-to-date on anything that seemed out of the ordinary, but was very self-sufficient and kept contact low but quality high until I returned. I trust her so much with my cats!

Availability updated yesterday

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