House Sitting Woodlawn

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Over 116
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1 / 1
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
47 reviews
17 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
Sitter Profile Image: Alexis W.
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Alexis W.
Star Sitter
from
$73
per night
5.0 out of 5 stars
30 reviews
8 repeat clients
5 years of experience
Chicago, IL, 60637

Alexis took great care of our home and pets during her second stay. She was communicative and thoughtful about updates and leaving our place tidy. Thanks again for sitting over the holiday! We'll be back. :-)

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Hannah C.
Sitter Profile Image: Jayden Phoenix (They/Them) P.
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Jayden Phoenix (They/Them) P.
Star Sitter
from
$66
per night
5.0 out of 5 stars
80 reviews
25 repeat clients
8 years of experience
Chicago, IL, 60620

Jayden was absolutely phenomenal! Our dog Calypso is very skittish with new people, and in the past, sitters have struggled to get her outside for potty breaks because she was too scared. Jayden was able to take Callie out a mere four hours after we left. Callie warmed up to them very quickly and snuggled a bunch, which is no small feat on Jayden's part. Jayden was very communicative and sent multiple updates a day, including photos and videos. They were quick to respond to messages, and they left our home spotless. I would love to book with them again for future trips!

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Kaitlyn B.
Sitter Profile Image: Dominique F.
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Dominique F.
from
$40
per night
4.6 out of 5 stars
73 reviews
39 repeat clients
16 years of experience
South Shore, Chicago, IL, 60637

Dominique did a great job with my 2 cats and 1 dog. She also took good care of my apartment. She sent me numerous of pictures and videos and also followed my instructions well especially pertaining to one of my cats who needs a little extra supervision. Thank you and I would book again.

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Cornelius D.
Sitter Profile Image: Victoria G.
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Victoria G.
from
$85
per night
5.0 out of 5 stars
29 reviews
4 repeat clients
21 years of experience
Hyde Park, Chicago, IL, 60615

Victoria watched my senior dog Oliver over Memorial Day weekend. Oliver had some medications that needed to be administered and Victoria did everything that was asked and went above and beyond for my boy. Leaving your pets with strangers in your house can be strange but any anxiety I had was gone upon meeting her and communicating before my departure date. She is super kind and detailed for all of your pets needs. She sent photos and updates throughout the weekend even when I was in an area with no cell service. I’d highly recommend Victoria to watch your pets.

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Kevin R.
Sitter Profile Image: Zoe R.
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Zoe R.
Star Sitter
from
$60
per night
5.0 out of 5 stars
14 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60615

Zoe watched our sweet pup and her cousin for an evening. She was on time (early), friendly, and sweet.

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Colleen S.
Sitter Profile Image: Danielle K.
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Danielle K.
from
$50
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
8 years of experience
Woodlawn, Chicago, IL, 60637

About: I have pet sit all kinds of loving dogs. Since I was 15 My family, friends and neighbors have trusted me to walk, feed, play with and care for their pets. I work full time virtually, so I am flexible and can care for your beloved pups while at home. I only have availability to do overnight boarding on weekends. I have a spacious place for your dog to have plenty of room to play and be comfortable. In addition, I have a dog park and a spacious park/field a walk away from my home. There also is a trail for us to walk as well. I am equipped to feed, walk and sing to your pup.

Sitter Profile Image: Claire P.
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Claire P.
from
$70
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
Sitter Profile Image: Maia S.
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Maia S.
from
$35
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60637

Maia was wonderful! She was communicative, responsible, and very professional. My puppy took to her very well. She even took him on a little adventure, which he sorely needed. As long as Maia is available I think I will continuously book her for house/dog sitting.

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anhri89@yahoo.com
Sitter Profile Image: Ava M.
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Ava M.
from
$55
per night
5.0 out of 5 stars
11 reviews
5 repeat clients
11 years of experience
Chicago, IL, 60621

Ava was wonderful with our 3 pups. She knew how to manage their chaos and treated them so sweetly. She left the place looking great and really just went above and beyond. We will definitely be using her services again.

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Gail S.
Sitter Profile Image: Jasmine P.
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Jasmine P.
from
$175
per night
5.0 out of 5 stars
98 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

Jasmine took excellent care of Zoey while we were out of town for nearly a week. Despite Zoey's nervousness and the challenges it posed initially, Jasmine exercised a lot of patience and willingness to try different things to allow Zoey to feel more safe. And after the first night, Zoey warmed up significantly! Jasmine kept us updated throughout the trip, whether it was the challenges on the first day or the big successes in the days that followed! We really appreciated Jasmine's skills, knowledge, and commitment to taking care of Zoey.

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Betty F.
Sitter Profile Image: Tamara C.
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Tamara C.
from
$50
per night
4.9 out of 5 stars
14 reviews
5 repeat clients
6 years of experience
Auburn Gresham, Chicago, IL, 60620

Was great with our 4 cats. We came back home and they were well taken care of. Provided pictures while we were gone and was helpful.

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Charmis D.
Sitter Profile Image: Manuela G.
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Manuela G.
from
$55
per night
5.0 out of 5 stars
28 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, IL, 60637

Manuela and Tomás are very friendly and warm people. They both are experienced dogsitters and ask the right questions, so you can leave your pup with them with peace of mind. They are respectful with your home. Can only highly recommend.

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Jaap S.
Sitter Profile Image: Sarah W.
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Sarah W.
from
$50
per night
3 years of experience
Woodlawn, Chicago, IL, 60637

About: Taking care of dogs was the first job I ever had. Neighbors would have me come over after school to check in with their babies and play with them or take them on walks. I've also been lucky enough to watch people's dogs while they were out of town; including puppies! Most recently, I volunteered at an animal shelter where we would take animals for walks, train them, bathe them, and shower them with love and treats! Every dog is unique, and I enjoy taking the time to get to know each animal and their family. I am currently working part-time with a flexible schedule, so I have plenty of time to accommodate specific schedules and adapt to individual needs. I always approach caring for animals with safety and respect as a first priority. It is important to me that both the dog and I are safe, and that I am attuned to their needs. I also want to prioritize respect for other people's space and time, so I make an effort to always be on time and adapt to any individual requests in people's homes.

Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$45
per night
5.0 out of 5 stars
31 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

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.

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Jenny L.
Sitter Profile Image: Kristen M.
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Kristen M.
from
$30
per night
10 years of experience
Hyde Park, Chicago, IL, 60637

About: I have experience taking care of all kinds of pets (mine and others) since I was a kid! Spent my life around all sizes of dogs, and I’m a lover of all cats! I’m a recent MA graduate, so my schedule is very open! I’m a very active person and enjoy walks, so I’m a great option to take your pup on midday walks! I have lots of experience around cats and dogs, so I will always make sure to help them feel comfortable in their space by building up trust between us!

Sitter Profile Image: Olivia H.
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Olivia H.
from
$50
per night
15 years of experience
Hyde Park, Chicago, IL, 60615

About: I have had 4 small dogs my whole life, but have also been a neighborhood pet sitter for dogs of all sizes for many years! I love all pups! I have Tuesdays and weekends off so I can spend the entire day with your pup while you’re away! We will go on walks and hang out outside :) I live in a dog friendly apartment. My apartment has a patio with access to a whole outdoor area where your pup can go potty and run around and sun bathe!

Sitter Profile Image: Bella B.
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Bella B.
from
$40
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60615

Bella did a great job with our pups. Great communication and she was very flexible working with our pack. I'd gladly have her back to watch them any time.

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Andrew M.
Sitter Profile Image: Niayla B.
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Niayla B.
from
$30
per night
5.0 out of 5 stars
18 reviews
4 repeat clients
12 years of experience
Hyde Park, Chicago, IL, 60613

Niayla was so responsive in setting up a last-minute dog sitting and answering all my questions, since this was my first time using Rover. She followed all instructions, reached out when she had questions, and sent regular photo updates. I felt good about leaving our home and pup in her hands and would hire her again.

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May E.
Sitter Profile Image: Julia G.
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Julia G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
6 years of experience
Hyde Park, Chicago, IL, 60614

About: Hello!! My name is Julia I’m 23 and I love animals. Ever since I was little I’ve always had a special interest in nature and animas especially cats! One of my favorite childhood memories is rescuing feral kittens in my neighborhood and finding homes for them. In my teens years I started dog and cat sitting for friends and family and ever cared for horses and rabbits in my high schools FFA. As of now I’m a painter and artist with a lot of time on my hands and would love to spend some quality time with your pets! When staying with a pet I like to follow a schedule for potty and feeding times since familiar routines can calm pets that might be anxious around new people :)

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

Pet parents share their Rover experiences - Woodlawn

1 / 1
5.0 out of 5 stars

Alexis took wonderful care of Cooper while I was away! She kept me updated with photos and videos throughout his stay, which gave me so much peace of mind. It was clear that Cooper was happy, comfortable, and well cared for. When I returned, my apartment was just as neat and clean as I had left it, which I really appreciated. Alexis was reliable, communicative, and treated both Cooper and my home with great care. I would absolutely recommend her to anyone looking for a trustworthy pet sitter, and I would gladly book with her again!

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Byron C.
House Sitting
5.0 out of 5 stars

Dominique did a great job with my 2 cats and 1 dog. She also took good care of my apartment. She sent me numerous of pictures and videos and also followed my instructions well especially pertaining to one of my cats who needs a little extra supervision. Thank you and I would book again.

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Cornelius D.
House Sitting
5.0 out of 5 stars

maia was wonderful, very communicative and respectful. peanutis an anxious dog and she was nice and calm when we got home. will definitely be booking her to hang out with peanut again

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Audrey T.
House Sitting
5.0 out of 5 stars

Mia took good care of Doby while I was away. She kept me updated with photos and she left my house clean and tidy. Knowing Doby was in such good hands made my vacation so much more relaxing. I would absolutely book Mia again for my next trip and highly recommend her to anyone looking for a caring and reliable dog sitter!

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Edie c.
House Sitting
5.0 out of 5 stars

Ava shared pictures and accurately followed all our instructions, we are very grateful for the boarding service provided =)

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Gabriel T.
House Sitting
5.0 out of 5 stars

Niayla was wonderful. It was my first time leaving my cat, Camille, at home by herself for two weeks and Niayla clearly gave her so much love, attention, and cuddles while I was gone. It really put my mind at ease to have someone in my home who so obviously truly cared for Camille. I could tell in all the photos and from the updates that they really enjoyed each other’s company and could not be more grateful to have found Niayla on this app!

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Sabrina M.
House Sitting
5.0 out of 5 stars

As usual, Staci was amazing with our cats and dog on our 10 day vacation. Zero complaints, great service, she goes above and beyond.

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Eleanor F.
House Sitting
5.0 out of 5 stars

Emily was an excellent dog sitter and I would hire her again. She was communicative and sent updates throughout the day which gave me great peace of mind. I never had to reach out and ask how my dog was doing because she proactively kept me informed. She was also accommodating with my dog’s feeding routine and mindful of his reactivity to bikes/scooters which I really appreciate. When I returned home everything was exactly as I had left it. I highly recommend Emily.

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Daritza H.
House Sitting
5.0 out of 5 stars

Rahmya was amazing! She was very flexible in setting up a meet and greet and instantly prioritized befriend Stormie. I got lots of updates and update pictures daily of stormie which made the whole process of being out of town much easier. I never felt like Stormie wasn't in good hands. The home was clean and perfectly tidy when we arrived back, which was so appreciated when returning from our trip. I would 100% recommend Rahmya for anyone looking for a pet sitter 💙

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Lillian W.
House Sitting
5.0 out of 5 stars

Bri does an absolutely incredible job! My dogs are obsessed with her and she send the best pics. She has also taken care of several issues w my house while she was house sitting. She is responsible and trustworthy, 100% recommend!

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Kate B.
House Sitting
5.0 out of 5 stars

Claire was fantastic. From the moment we met her, she was warm, professional, and clearly experienced with dogs. She took exceptional care of my anxious dog, Balu, and we were so relieved to come home to a relaxed, happy dog. Claire kept us updated with photos and messages throughout our trip, which gave us real peace of mind while we were away. She stayed in our home and left everything spotless. We couldn’t have asked for a better dog sitter and wouldn’t hesitate to book her again if she’s available.

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Jay N.
House Sitting
5.0 out of 5 stars

Lucille is an incredibly kind and attentive cat sitter. She made him feel loved and played with him so much. She even took him for a stroll on his backpack. Would highly recommend. Felt like our baby was in wonderful hands!

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Joanna A.
House Sitting
5.0 out of 5 stars

Phenomenal. Anais took great care of our doges and home. She was extremely responsive to our messages and sent update pictures every day.

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Gabriel L.
House Sitting
5.0 out of 5 stars

Diana did an amazing job watching my dog while I was away. Highly recommend for your pet sitting needs.

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Jommel M.
House Sitting
5.0 out of 5 stars

Jasmine is the epitome of caring combined with professionalism. She took care of my small shorkie for an extended stay and when i returned my pet was calm and well cared for. Jasmine checked in every day with a quick message update and pics to let me know how things were coming along. She even checked in on the plants as well. Highly recommend this sitter and will use her again

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yvonne b.
House Sitting
5.0 out of 5 stars

Dahlia was fantastic to work with. She was great at communicating and sent daily updates of our pups while we were out of town. I felt confident our pets were well cared for. She was respectful of our home as well. I would definitely recommend Dahlia for any housesitting and pet needs.

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Sarah H.
House Sitting
5.0 out of 5 stars

Marlicia is the best!!! She is a wonderful dog sitter and home sitter as well. My husband and I have used her three times now and will continue to do so whenever possible, she is attentive to the dogs schedules and routines, sends multiple updates and is always easy to get a hold of if needed. We can tell our dogs enjoy their time with her as well, when we come home they are relaxed and happy, which is truly the piece of mind we need. She also has had to manage random scenarios that came up and is so go with the flow. For example The first time we used her services she had to facilitate our movers dropping off all our stuff while we were on a cruise and not reachable for some time 😱 she also even gave us a present when we came back from our wedding trip, which meant a lot to us! she is excellent at long stays as well, all three times we have had her stay with the dogs we were gone for 8-10 days. Plus she is able to walk our 90lb Doberman and 50lb Aussie at the same time (not easy to do at all!) and we could tell she had experience with all different dog breeds and sizes. I cannot recommend her enough!

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Alyssa B.
House Sitting
5.0 out of 5 stars

Laurel was so sweet and dog sat for us while we were in Chicago and we couldn’t be more pleased with the experience. I wouldn’t hesitate to book with her again and I think Gram would say the same. :)

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Miranda H.
House Sitting
5.0 out of 5 stars

Evan was terrific - great with the dogs, good communicator, and he left the house in wonderful condition. We booked him at the last minute and would definitely book him again. Highly recommended.

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Cynthia H.
House Sitting
5.0 out of 5 stars

Leah was great. Communication with her was easy and she was very accommodating to my busy schedule. Sent me plenty of pics of my babies while I was away. Would definitely work with her again!

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Jasmine M.
House Sitting
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Sitters in Woodlawn average 4
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