House Sitting in Woodlawn, 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
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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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1. Emily N.

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

Emily was great with my senior pup, Bailey! She kept me updated and sent great photos the entire time I was out of town. On top of the great care she took with both Bailey and my place, she was amazingly flexible and able to extend her stay when we had to stay out of town an extra day. Definitely recommend Emily and plan to book again with her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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2. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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3. Jasmine P.

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

Jasmine exceeded our expectations caring for our 3 dogs and 1 cat over the long weekend. She was incredibly communicative, regularly sending updates and photos which put our minds at ease. Our animals seemed happy and well taken care of upon our return. We highly recommend Jasmine for anyone in need of reliable and loving pet care!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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4. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$44
per night

Chijioke is one of the most caring and empathetic caregivers I have ever met. My cat easily fell in love and felt safe around them for cuddles and play times. They took extra care to make sure she and her litter space were clean. As well as training her on what are her dedicated spaces versus where she's not allowed like in the bathroom tub lol They have been super helpful in guiding me on how to be a better pet parent every time we meet. Very grateful to have them as my and my cat's best friend!

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Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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5. Nicole C.

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

Nicole is awesome. She stayed with our pups over 6 days in our home. She followed all our instructions and treated the pups like her own. She catered to their individual personalities and needs. Awesome communication and lots of photos. Nicole continued caring for the dogs even though she got sick that weekend. She left our place spotless. Highly recommend!

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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6. Belicia K.

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

My cat sitter cancelled on me at the last minute. But as it turns out I was meant to find Belicia. She took excellent care of my girl Zuri. Belicia was communicative, kind, and followed all instructions. She sent me messages and photos to absolve any worry and it didn't take long for my anti-social kitty to take to her. Having her care for Zuri was such a peace of mind. When I came back home, I realize that everything worked out as it should have. This is the beginning, as I will be scheduling with Belicia again.

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
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
7 repeat clients
from
$75
per night

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!!?

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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8. Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
16 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: Memorial Day Weekend
Sitter Profile Image: Jacky & Leo V.
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Sitter Profile Image: Jacky & Leo V.
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9. Jacky & Leo V.

A dog is also a girls best friend!
Chicago, IL, 60636
3.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
8 repeat clients
from
$50
per night

Jacky was wonderful! So quick and easy to communicate and set up a meet and greet with. We needed dog sitting for a weekend. Our dogs are reactive to people and after explaining this to Jacky, she was up for seeing if it will work. My dogs took to her very quickly!! We got updates and pictures, including how well they were acclimating to her! We can’t thank her enough and will definitely be booking her services again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dominique F.
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Sitter Profile Image: Dominique F.
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10. Dominique F.

Caring For Your Pet With Respect❤️
South Shore, Chicago, IL, 60637
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
35 repeat clients
from
$65
per night

About: Hi I'm Dominique, here to get out and walk Dogs or just be a friendly companion for your pets. I understand deeply the responsibility of careing for and loving our furry friends. What's better than knowing your furry friend is happy and healthy especially after being back from a busy day, or just knowing someone is there to help when your just not feeling good! That someone is me! I couldn't have found a better Gig! All animals deserve the attention they desire! They deserve to live a good life and get fresh air. I'll be there as a helping hand so please be detailed as possible with your pets individual needs and I assure a great visit. I'm a full time worker for rover, I have a 1 bed apartment in Pilsen very dog friendly neighborhood. I am available so contact me 😊 thank you. I have been caring for animals my whole life I have their best interest. Thanks for choosing river I am available full time. Contact me anytime!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jessica S.
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Sitter Profile Image: Jessica S.
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11. Jessica S.

Passionate Pet Care Pro
Chicago, IL, 60649
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$30
per night

Jessica is simply the best when it comes to pet care! She's like a second mom to our furry family members. Always reliable and caring, Jessica goes out of her way to make sure our pets are happy and healthy. We couldn't ask for a better caregiver! Thanks, Jessica, for all you do!

Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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12. John M.

UChicago student; animal lover
Hyde Park, Chicago, IL, 60637
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$50
per night

John is excellent with both cats and dogs. He is incredibly patient and gentle with my cats who I have left in his care several times. John is also a big dog-lover and has cared for his three dogs for many years. John is reliable and dependable and will take excellent care of your pets!

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Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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13. Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
22 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: Thomas B.
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Sitter Profile Image: Thomas B.
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14. Thomas B.

Dogs love me and cats adore me
Grand Crossing, Chicago, IL, 60619
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 years of experience
from
$50
per night

About: I've spent time with dogs when I visited my aunt. She loved them and so do I. I also have 3 cats of my own and there all healthy boys. I've pet sit my friends house and his two dogs for a week once and it wasnt bad at all. I want to make your pet feel safe even when your not around. I can do all breeds of dogs and cats if you need your lazy feline friends to be watched. If you want someone who knows dogs and cats and want them to be safe I am your guy. You can rest assure they will be played with fed and happy the time your away. I'm ready to lend a paw to you.

Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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15. Danielle B.

I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night

Being an animal lover myself, I can wholeheartedly vouch for Danielle as the perfect pet sitter. Her genuine love for furry pets is unparalleled, making her not just the perfect caregiver, but also a trusted companion to your beloved pets. Danielle has an innate understanding of animals' needs and behaviours as she has grown up and lived with pets her whole life. She will ensure that your pets will feel comfortable and loved for in her care. Her responsible and attentive nature means you can rest assured knowing that your furry family members are in the best hands possible. What sets Danielle apart is her unwavering dedication to the well-being of animals. Whether it's going the extra mile to ensure they get enough exercise, providing them with affectionate cuddles, or even just spending quality time with them, Danielle treats every pet as if they were her own. I have seen firsthand the joy and peace of mind Danielle brings to pet owners. With Danielle as your pet sitter, you can enjoy your time away knowing that your pets are not just looked after, but genuinely cared for. Go Danielle! <3

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Sitter Profile Image: Grace T.
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Sitter Profile Image: Grace T.
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16. Grace T.

Full time student & pet lover!
Woodlawn, Chicago, IL, 60637
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 years of experience
from
$30
per night

About: Experience with dogs and cats. Full time student which gives me more flexibility to attend to your pet! I’ve worked with mostly medium sized high energy dogs. I am a graduate student here in Chicago so I can be flexible with attending to pets on week days and weekends. I also have a car so I can be quick to get to locations I love being attentive to pets and their needs whether it’s playing, going on walks, potty breaks, and keeping track of food and water intake.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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17. Emily L.

Love all pets 🫶
Hyde Park, Chicago, IL, 60637
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$60
per night

About: I’ve had a few pets of my own and I am very detail oriented, if your pets ever need me to go an extra mile I will! I am currently a college students at the University of Chicago. I have free time after classes, on weekends and some holidays. I would love to work as a pet sitter or walker! I won’t be home sitting because I live in a dorm right now, but I can home sit at your homes! I care very much for animals and will give them my undivided attention.

Sitter Profile Image: Jonah S.
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Sitter Profile Image: Jonah S.
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18. Jonah S.

Around HP - flexible schedule
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$60
per night

Jonah dog sat Cinnamon and he did a great job with her! I appreciate the daily updates while I was away and that he kept my place tidy. Thank you, Jonah! I will be calling Jonah again in the future.

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

We love making new furry friends!
Chicago, IL, 60637
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$85
per night

Emma and Emily were easy to work with. They are professional, courteous, friendly, and clearly love being with dogs. They took excellent care of our senior dog, and it was clear that she was very happy to be with them. I would definitely use them again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jumie T.
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Sitter Profile Image: Jumie T.
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20. Jumie T.

Dogs love me!
Chicago, IL, 60649
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
1 repeat client
from
$50
per night

About: I am an artist and former dog owner with experience working as a private dog sitter since high school. I love pets immensely, and am so excited to meet yours! Every dog I get to greet is a gift, and I treat them as such. Through my own experience as a dog owner, and diverse experience with other dogs, I have learned a lot that I get to bring to these new situations. I know how vital calmness can be, and keep myself patient. I know every dog is different, so please share everything you can about your animal and all their quirks! Getting to interact with animals is so much fun and so fulfilling, I wish to spend more of my time doing it when I can. I currently work from home, so my schedule is incredibly flexible! I'm available for walks throughout the week and can stay with your fur baby as need be. I like to keep the care of your pet as close as possible to their normal routine, so please keep that information clearly written out if possible, or we can talk through it together.

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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