House Sitting in Grand Boulevard, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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1. Lindsay J.

Star Sitter
Cat mom and animal lover
Chicago, IL, 60642
6.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
43 reviews
10 repeat clients
from
$64
per night

Lindsay is great! I travel regularly for work and she is always willing and able to accommodate the early departures and late arrival. She’s very respectful of my place and sends constant updates. My dog loves her and I book her regularly.

Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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2. Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
54 reviews
25 repeat clients
from
$65
per night

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!

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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3. Emily N.

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

Emily was amazing! She took care of my senior dog and cat while I was away for the weekend and sent me pictures and updates on how each was doing throughout. My senior dog is a rescue and can get anxious when I leave but he seemed to be so comfortable with Emily and was super calm during the weekend. I’ll be using Emily again next time I go out of town!

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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4. Belicia K.

Star Sitter
Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
2.0 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: Saniah I.
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Sitter Profile Image: Saniah I.
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5. Saniah I.

Star Sitter
Saniah: Your pets, my love!
Chicago, IL, 60605
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night

Arrived in time and take care of my dog perfectly, great communication all the time, definitely recommend her and super happy with the service provided.

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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6. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$65
per night

Crystal responded to my cat sitting request quickly, asked great questions, followed all directions, and my kittens loved her. I will definitely try to book with her in the future!

Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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7. Callie L.

I love caring for animals!!
Near West Side, Chicago, IL, 60607
4.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
5 repeat clients
from
$50
per night

We were gone a week and knew our Marley and house were in great hands. We have had Callie come see our baby several times before and this time house sit and we don't want to have anyone else take care of her. Our house was well taken care of and my girl is happy, what else could we ask for. I am a hover Mom and Callie just rolled with it and let me know she was doing fine and sent pics and I was able to relax. We can't thank you enough. Callie.

Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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8. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$33
per night

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 ?

Sitter Profile Image: Araceli G.
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Sitter Profile Image: Araceli G.
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9. Araceli G.

caring & responsible pet sitter
Near West Side, Chicago, IL, 60607
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
25 reviews
7 repeat clients
from
$50
per night

Araceli is the best!! My dog was recovering from an injury and needed to be watched closely and given medicine while we were gone and she went above and beyond to make sure he was resting and healing and that I felt reassured while being away. She even picked up more medicine when needed. She was responsive and flexible as our travel plans changed. Araceli will take the absolute best care of your pet! She makes a stressful situation much less. Can’t recommend her enough!!

Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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10. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
15 repeat clients
from
$88
per night

This is the second time that Johnathan has housesat for us and watched our puppy Ollie. Ollie loved him, and he kept us updated with messages and pictures. We definitely recommend him!

Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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11. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$60
per night

Sujae did a great job carrying for my furry crew when I had to travel!

Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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12. Jasmine P.

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

Jasmine took great care of our dog, Koji, while Koji was a little sick and we had to be out of the house over the weekend. Jasmine came on time, even when we needed her early in the morning, and proactively took Koji on walks every few hours to ensure she had relief from her upset tummy. Koji was happy and relaxed when we came home after spending the day with Jasmine! I’d highly recommend her.

Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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13. Danielle B.

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

Danielle was great at taking care of my two large dogs. She was very affectionate with my dogs, ensured they got a lot of attention, an brought them on walks where they were able to run freely in the park to get their energy out. Danielle provided me with detailed updates which gave me peace of mind while I was away from my dogs. I would recommend Danielle and would gladly work with her again.

Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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14. Nicole C.

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

Nicole went above and beyond what we could've asked for from a sitter. She stayed at our place for a week and looked after our two boys. Our youngest Vinny had started to have a little bit of diarrhea before we left for vacation, but we thought it would pass with some water and a few extra potty breaks. A few days into her stay, it was apparent it was getting worse, so we got in contact with our vet and arranged for testing and meds. Nicole handled everything with the vet and the boys so fast, and was so communicative and organized. And I know Vinny - he's a handful on his own, but with a tummy ache, you need to keep your eyes on him 24/7, and she did just that. I'm so thankful to have had someone take care of him the way I would. We also have this little ritual we keep with our pup Rusty's memorial (he passed a year ago). She kept up our little routine and gave us updates on him too :) We just off-handedly told her it was a thing we do, and the fact that she kept it up meant so much. I could ramble on forever! Bottom line, Nicole is an exceptional sitter/person and I would 10000% trust her with my boys again.

Sitter Profile Image: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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15. Ashleigh H.

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
3.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$30
per night

Ashleigh was great with my pups! I have two dachshunds - one is very energetic and the other has separation anxiety. She made sure to take them on lots of walks and give them lots of snuggles. Normally when I'm gone, they don't eat and I come home to two overly-clingy dogs. This time, they were well-fed and didn't really seem to care that I was home. She also sent lots of updates so I always knew how they were doing. Not only were my dogs happy, I also came home to a spotless house. I will definitely book Ashleigh again!

Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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16. Sarah S.

Rover 101
Experienced Animal Care
Bridgeport, Chicago, IL, 60609
1.6 mi. away
House Sitting
5.0 out of 5 stars
57 reviews
12 repeat clients
from
$60
per night

Sarah did a great job with Hazel and Apollo. This was the first time we have left them with a sitter (other than a family member), so we were a bit nervous, but once I asked for some updates and photos, Sarah was good about sending them! She was very prompt with her arrival times and our dogs seemed comfortable with her from the beginning.

Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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17. Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
1.2 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!

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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18. Katherine B.

Star Sitter
🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
0.7 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.

Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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19. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
5 repeat clients
from
$60
per night

Abi was wonderful!! So respectful of our home and our dog was well loved while we were away!

Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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20. Masheika S.

Rover 101
All around animal lover 💜🐾
Chicago, IL, 60653
0.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
61 reviews
21 repeat clients
from
$100
per night

Masheika is awesome and I am pretty sure my dog would leave me for her. During her time sitting, she stayed in regular contact with updates and photos. I felt completely confident and comfortable with her and will definitely, definitely re-book if we ever get to go out of town again. During the meet and greet, I could immediately tell Masheika the kind of special spirit that animals gravitate towards. My dog was immediately stuck to her side and I felt completely assured that they would be great while I was gone. He's a very sensitive dog and it was so comforting knowing that he was being taken care of by a caring person instead of being kept in a kennel. Highly recommend!!

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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.

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