Pet Sitting & Drop Ins in Douglas, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Douglas pet sitters

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Sitter Profile Image: Cassandra H.
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Cassandra H.
from
$20
per visit
5 out of 5.0 stars
57 reviews
21 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.

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Sud R.
Sitter Profile Image: molly m.
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molly m.
from
$22
per visit
5 out of 4.9 stars
257 reviews
73 repeat clients
7 years of experience
Loop, Chicago, IL, 60607

Great sitter! Molly was very patient and flexible when things went awry at my apartment complex. She took good care of my cats and my apartment while I was gone and I would book her again!

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Pheobe H.
Sitter Profile Image: Eunice Y.
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Eunice Y.
from
$22
per visit
5 out of 5.0 stars
7 reviews
1 repeat client
4 years of experience
Loop, Chicago, IL, 60607

I have booked with Eunice multiple times now (some very last minute bookings) and she always does a great job checking in and taking care of my Doberman. Eunice always makes sure my energetic dog gets enough attention and exercise throughout the visit.

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Asia A.
Sitter Profile Image: Molly G.
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Molly G.
Star Sitter
from
$16
per visit
5 out of 5.0 stars
11 reviews
4 repeat clients
16 years of experience
Bridgeport, Chicago, IL, 60608

Molly did drop-in visits for my cat Maizie while I was out of town and she was great! Maizie can be shy and anxious with new people and Molly was very patient with her. Molly was also willing to administer Maizie's daily oral medication (and to build the necessary trust with Maizie to do so), which was very important to me. I also appreciated how communicative Molly was and how quickly she responded to questions I had while I was away. I would definitely recommend Molly for cat-sitting/cat care!

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Esther I.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$22
per visit
5 out of 4.9 stars
33 reviews
8 repeat clients
21 years of experience
Lower West Side, Chicago, IL, 60608

Sarah is professional, caring, and communicative and gave regular updates which I really appreciated. My cat was totally relaxed when I got home. Sarah is my new go to cat sitter!

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Zoe A.
Sitter Profile Image: Paige B.
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Paige B.
from
$16
per visit
5 out of 5.0 stars
13 reviews
2 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60616

Paige was awesome and sent me the cutest photos of tai. I had to book last minute and she was awesome

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Alyssa S.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$17
per visit
5 out of 5.0 stars
69 reviews
22 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Qutress was amazing with our cat as always! She took care of everything exactly as requested and we felt super comfortable knowing that our pet was in such good hands while we were out of town.

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Max H.
Sitter Profile Image: Erin M.
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Erin M.
from
$19
per visit
5 out of 5.0 stars
74 reviews
17 repeat clients
4 years of experience
Bridgeport, Chicago, IL, 60608

Erin, you are the best! Thank you for being so communicative and making us feel close to our babies, even though we were so far away. It feels like Kitty and Baby’s bond is closer, and I think it’s from your magic. :) Very dependable and I can tell you love caring for animals. Also your wedding gift to us was so sweet!! We cried when we seen it. You go the extra mile, so very kind. Definitely will message you the next time we need someone to look after our cats. We are grateful for you, and so are Baby and Kitty.

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Lex V.
Sitter Profile Image: Brianna J.
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Brianna J.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
10 reviews
3 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Thank you for a great job!

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Jim C.
Sitter Profile Image: David K.
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David K.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
123 reviews
42 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60616

David watched our cat Violet while we were away for a week. He’s very dependable and did a great job taking care of her and giving her medications. Will book again next time we’re out of town!

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Caroline F.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per visit
5 out of 5.0 stars
128 reviews
45 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Tamara has been a wonderful support to our family. She’s a quick learner, is patient and communicates well. Our team pups enjoy her and always look forward to their walks with her.

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Elizabeth & Monica H.
Sitter Profile Image: Chayse T.
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Chayse T.
from
$20
per visit
5 out of 5.0 stars
30 reviews
10 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60616

Super kind and very communicative! Definitely appreciate Chayse helping out! ?

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Tirzah K.
Sitter Profile Image: Xinwen M.
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Xinwen M.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
32 reviews
8 repeat clients
3 years of experience
Armour Square, Chicago, IL, 60616

Xinwen was amazing!! She watched my cat for over a week and through Christmas and she was very consistent and did everything Goji needed. She also took great pictures and left detailed overviews of what occurred during her visits. She is very kind and I would recommend her to anyone I know who needs a sitter!

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Kailey A.
Sitter Profile Image: Mariam A.
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Mariam A.
from
$14
per visit
5 out of 5.0 stars
4 reviews
4 years of experience
Bridgeport, Chicago, IL, 60608

Mariam did a fantastic job watching our cat! She was very communicative and professional; she updated us after every visit and sent lots of pictures. 10/10 would recommend and will be using her services again!!

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Mae J.
Sitter Profile Image: Kai H.
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Kai H.
Star Sitter
from
$17
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
13 years of experience
Bridgeport, Chicago, IL, 60616

I lucked out! I had a last minute personal matter, and Kai was quick to let me know what worked best. Papito was happy with his house visit and seemed relaxed. Would happily trust Kai with future drop-in visits.

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Mateo O.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$30
per visit
5 out of 5.0 stars
13 reviews
5 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.

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Petia O.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$30
per visit
5 out of 5.0 stars
30 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

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Lillian & Jason A.
Sitter Profile Image: Andrea H.
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Andrea H.
from
$18
per visit
5 out of 5.0 stars
9 reviews
20 years of experience
Douglas, Chicago, IL, 60616

About: I just love all animals! Taking care of them just always came natural to me. Never met a single one that I couldn’t connect with! Currently I am available Friday-Sunday. I do have some flexibility depending on where you are located and the services you would like. Just message me and we can work something out! I will take care of your pets exactly how you want me to. Nothing less! I understand leaving a fur baby in the care of others can be nerve wrecking. I want to give my clients as much peace as possible.

Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$15
per visit
5 out of 5.0 stars
10 reviews
6 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Jozelin did great with my cat, Bella! I got pictures daily, as well as updates about her behavior and any issues. When I got home from my week long trip, Bella was doing great and had clearly been well taken care of! I would book Jozelin again - especially because she tool the time to get to know Bella and gain her trust!

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Emily V.
Sitter Profile Image: Julie M.
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Julie M.
from
$25
per visit
2 years of experience
Douglas, Chicago, IL, 60616

About: I have taken care of my friends pets for years. It’s been Cats and dogs and each experience has made me love animals even more! I currently have open availability. I’m my availability allows me to spend more time with your pet and can typically accommodate last minute requests easier. I will learn the everything about the clients home to make sure all safety precautions are taking. I ask a lot of questions to understand everything.

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Sitter Profile Image: Cassandra H.
Verified Enhanced Background Check
Sitter Profile Image: Cassandra H.
Verified Enhanced Background Check

Cassandra H.

Life-long animal lover!
Hyde Park, Chicago, IL, 60615
2.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 5.0 stars
57 reviews
21 repeat clients
Profile image

Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.

Availability updated 4 days ago
Sitter Profile Image: molly m.
Verified Enhanced Background Check
Sitter Profile Image: molly m.
Verified Enhanced Background Check

molly m.

I will love them like my own!
Loop, Chicago, IL, 60607
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$22
per visit
5 out of 4.9 stars
257 reviews
73 repeat clients
Profile image

Great sitter! Molly was very patient and flexible when things went awry at my apartment complex. She took good care of my cats and my apartment while I was gone and I would book her again!

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Eunice Y.
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Sitter Profile Image: Eunice Y.
Verified Enhanced Background Check

Eunice Y.

A WFH dog mom
Loop, Chicago, IL, 60607
2.6 mi. away
Drop-In Visits, Dog Walking
from
$22
per visit
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

I have booked with Eunice multiple times now (some very last minute bookings) and she always does a great job checking in and taking care of my Doberman. Eunice always makes sure my energetic dog gets enough attention and exercise throughout the visit.

Availability updated today
Sitter Profile Image: Molly G.
Verified Enhanced Background Check
Sitter Profile Image: Molly G.
Verified Enhanced Background Check

Molly G.
Star Sitter

Reliable, friendly, and caring!
Bridgeport, Chicago, IL, 60608
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per visit
5 out of 5.0 stars
11 reviews
4 repeat clients
Profile image

Molly did drop-in visits for my cat Maizie while I was out of town and she was great! Maizie can be shy and anxious with new people and Molly was very patient with her. Molly was also willing to administer Maizie's daily oral medication (and to build the necessary trust with Maizie to do so), which was very important to me. I also appreciated how communicative Molly was and how quickly she responded to questions I had while I was away. I would definitely recommend Molly for cat-sitting/cat care!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Sarah B.
Verified Enhanced Background Check
Sitter Profile Image: Sarah B.
Verified Enhanced Background Check

Sarah B.
Star Sitter

Pet Sitter in Pilsen
Lower West Side, Chicago, IL, 60608
2.2 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$22
per visit
5 out of 4.9 stars
33 reviews
8 repeat clients
Profile image

Sarah is professional, caring, and communicative and gave regular updates which I really appreciated. My cat was totally relaxed when I got home. Sarah is my new go to cat sitter!

Availability updated 2 days ago
Sitter Profile Image: Paige B.
Verified Enhanced Background Check
Sitter Profile Image: Paige B.
Verified Enhanced Background Check

Paige B.

Animal lover and caretaker!
Near South Side, Chicago, IL, 60616
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per visit
5 out of 5.0 stars
13 reviews
2 repeat clients
Profile image

Paige was awesome and sent me the cutest photos of tai. I had to book last minute and she was awesome

Availability updated 11 days ago
Sitter Profile Image: Qutress T.
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Sitter Profile Image: Qutress T.
Verified Enhanced Background Check

Qutress T.
Star Sitter

a dog-person without dogs
Grand Boulevard, Chicago, IL, 60615
2.2 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
69 reviews
22 repeat clients
Profile image

Qutress was amazing with our cat as always! She took care of everything exactly as requested and we felt super comfortable knowing that our pet was in such good hands while we were out of town.

Availability updated 4 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Erin M.
Verified Enhanced Background Check
Sitter Profile Image: Erin M.
Verified Enhanced Background Check

Erin M.

Reliable care for your pet
Bridgeport, Chicago, IL, 60608
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$19
per visit
5 out of 5.0 stars
74 reviews
17 repeat clients
Profile image

Erin, you are the best! Thank you for being so communicative and making us feel close to our babies, even though we were so far away. It feels like Kitty and Baby’s bond is closer, and I think it’s from your magic. :) Very dependable and I can tell you love caring for animals. Also your wedding gift to us was so sweet!! We cried when we seen it. You go the extra mile, so very kind. Definitely will message you the next time we need someone to look after our cats. We are grateful for you, and so are Baby and Kitty.

Availability updated 5 days ago
Sitter Profile Image: Brianna J.
Verified Enhanced Background Check
Sitter Profile Image: Brianna J.
Verified Enhanced Background Check

Brianna J.
Star Sitter

Expert belly rubber & bum scratcher
Grand Boulevard, Chicago, IL, 60653
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
10 reviews
3 repeat clients
Profile image

Thank you for a great job!

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
Verified Enhanced Background Check

David K.
Star Sitter

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
123 reviews
42 repeat clients
Profile image

David watched our cat Violet while we were away for a week. He’s very dependable and did a great job taking care of her and giving her medications. Will book again next time we’re out of town!

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tamara J.
Verified Enhanced Background Check
Sitter Profile Image: Tamara J.
Verified Enhanced Background Check

Tamara J.
Star Sitter

Experienced Dog Owner
Grand Boulevard, Chicago, IL, 60653
1.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per visit
5 out of 5.0 stars
128 reviews
45 repeat clients
Profile image

Tamara has been a wonderful support to our family. She’s a quick learner, is patient and communicates well. Our team pups enjoy her and always look forward to their walks with her.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Chayse T.
Verified Background Check
Sitter Profile Image: Chayse T.
Verified Background Check

Chayse T.

Well-Versed in Petcare
Near South Side, Chicago, IL, 60616
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 5.0 stars
30 reviews
10 repeat clients
Profile image

Super kind and very communicative! Definitely appreciate Chayse helping out! ?

Availability updated 30 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Xinwen M.
Verified Enhanced Background Check
Sitter Profile Image: Xinwen M.
Verified Enhanced Background Check

Xinwen M.
Star Sitter

A 200% genuine petlover!
Armour Square, Chicago, IL, 60616
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 5.0 stars
32 reviews
8 repeat clients
Profile image

Xinwen was amazing!! She watched my cat for over a week and through Christmas and she was very consistent and did everything Goji needed. She also took great pictures and left detailed overviews of what occurred during her visits. She is very kind and I would recommend her to anyone I know who needs a sitter!

Availability updated 24 days ago
Sitter Profile Image: Mariam A.
Verified Enhanced Background Check
Sitter Profile Image: Mariam A.
Verified Enhanced Background Check

Mariam A.

Experienced Pet Sitter in Chicago
Bridgeport, Chicago, IL, 60608
1.7 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
5 out of 5.0 stars
4 reviews
Profile image

Mariam did a fantastic job watching our cat! She was very communicative and professional; she updated us after every visit and sent lots of pictures. 10/10 would recommend and will be using her services again!!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kai H.
Verified Enhanced Background Check
Sitter Profile Image: Kai H.
Verified Enhanced Background Check

Kai H.
Star Sitter

Pawsitively passionate about pets!
Bridgeport, Chicago, IL, 60616
1.1 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

I lucked out! I had a last minute personal matter, and Kai was quick to let me know what worked best. Papito was happy with his house visit and seemed relaxed. Would happily trust Kai with future drop-in visits.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Daphnay S.
Verified Enhanced Background Check
Sitter Profile Image: Daphnay S.
Verified Enhanced Background Check

Daphnay S.
Star Sitter

Dog Lover and Owner
Douglas, Chicago, IL, 60653
0.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$30
per visit
5 out of 5.0 stars
13 reviews
5 repeat clients
Profile image

Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.

Availability updated 5 days ago
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check

Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5 out of 5.0 stars
30 reviews
8 repeat clients
Profile image

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

Availability updated 2 days ago
Sitter Profile Image: Andrea H.
Verified Enhanced Background Check
Sitter Profile Image: Andrea H.
Verified Enhanced Background Check

Andrea H.

Animal lover ❤️
Douglas, Chicago, IL, 60616
0.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per visit
5 out of 5.0 stars
9 reviews

Andrea is the best, has her watch my dog Charming for a weekend. She followed all the instructions I left for her and also made sure that Charming took all his medication. She is an exceptional caretaker was very knowledgeable, reliable, efficient and devoted. She clearly has a love for animals and I will be using her again.

Availability updated 5 months ago
Sitter Profile Image: Jozelin R.
Verified Background Check
Sitter Profile Image: Jozelin R.
Verified Background Check

Jozelin R.

Experienced Petsitter/Dog Walker 🙂
Bridgeport, Chicago, IL, 60616
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
10 reviews
6 repeat clients
Profile image

Jozelin did great with my cat, Bella! I got pictures daily, as well as updates about her behavior and any issues. When I got home from my week long trip, Bella was doing great and had clearly been well taken care of! I would book Jozelin again - especially because she tool the time to get to know Bella and gain her trust!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Julie M.
Verified Enhanced Background Check
Sitter Profile Image: Julie M.
Verified Enhanced Background Check

Julie M.

Animal lover ready to care your pet
Douglas, Chicago, IL, 60616
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
3 reviews

Julie takes great care of her own cat as well as others. She watched my cat Pippin a few different times when i was out of town and he was well taken care of and happy the whole time. A true cat lover, she would treat your cat like her own and make sure to give the best care!

Availability updated 3 days ago
Confirmed availability for Labor Day Weekend

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