House Sitting in Grand Boulevard, 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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What size are your dogs (lbs)?

Search Results

Confirmed availability: Easter Weekend
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1.

Crystal R.

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
80 reviews
36 repeat clients
from
$65
per night

Crystal did an absolutely wonderful job taking care of our senior dog. She went above and beyond to make sure our Ollie was happy and well taken care of. She sent pictures and updates daily. We plan to use her services again, and highly recommend her!!

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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2.

Saniah I.

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
10 reviews
2 repeat clients
from
$50
per night

Saniah is great! She was on time and clearly showed that she cares for animals, asking about our dog’s favorite toys and treats. I felt entirely comfortable leaving our dog with her in our home and we will be using her again!

Sitter Profile Image: Caroline M.
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Sitter Profile Image: Caroline M.
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3.

Caroline M.

Experienced dog sitter
Chicago, IL, 60637
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
1 repeat client
from
$130
per night

Caroline is a fantastic dog sitter! She is timely, respectful, and loving to all animals! She has stayed in our house and watched our two large dogs many times, and we trust her with their lives without question. She is reliable, kind, and caring. We will continue to book her!

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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4.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60616
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
190 reviews
83 repeat clients
from
$70
per night

Dalila took such great care of my fur baby. This was my first time having someone watch my dog while housesitting! She sent me pictures daily, updated me constantly and left the house super clean and my dog super happy ? I will def rebook again!!

Sitter Profile Image: Annie B.
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Sitter Profile Image: Annie B.
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5.

Annie B.

Large or Small - I Love 'em All!
Loop, Chicago, IL, 60605
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
65 reviews
32 repeat clients
from
$100
per night

Annie took great care of our pup and even took her to a friends when we needed her to be moved while away. Millie loved her instantly and she always leaves our house spotless!

Confirmed availability: Easter Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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6.

Jasmine P.

Rover 101
Beloved dog whisperer, is me!
Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
55 reviews
20 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: Belicia K.
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Sitter Profile Image: Belicia K.
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7.

Belicia K.

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

Belicia is the absolute best. We were gone for two weeks for our wedding abroad and were so busy that we barely had time to check in the way we normally would. Yet, Belicia made a daily effort to give us the loveliest updates about her time with our girl, giving us total peace of mind.

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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8.

Emily N.

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
106 reviews
31 repeat clients
from
$55
per night

Emily is great! She checked in often and took excellent care of Maeve and McKenna - we look forward to working with her again soon and will definitely recommend her to friends.

Sitter Profile Image: Shiri B.
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Sitter Profile Image: Shiri B.
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9.

Shiri B.

Kind and practical pet lover
Chicago, IL, 60621
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
from
$50
per night

Shiri was awesome to accept a relatively last minute booking at a good rate, and was communicative and professional throughout her stay. I returned to my home exactly how I had left it for her which I appreciated as well. She was understanding and kind when problems arose which meant a lot for me given my dog is of old age and caring for him can be quite involved. Thanks Shiri!

Confirmed availability: Easter Weekend
Sitter Profile Image: Angelica V.
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Sitter Profile Image: Angelica V.
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10.

Angelica V.

I love dogs!
Chicago, IL, 60608
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$40
per night

She walked my dog while I was at work and was always reliable, trustworthy going into my home, and great with my pup. She is great!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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11.

Katherine B.

🐶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
53 reviews
15 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: Easter Weekend
Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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12.

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
60 reviews
21 repeat clients
from
$100
per night

Masheika was a fantastic sitter for our dog Leon! We were looking for someone to stay with him for two nights on short notice, and we were so grateful to her! She even accommodated a meet and greet with Leon a few days before to make sure he would recognize her. She sent a ton of pictures so we knew he was in good hands. He got lots of walks, and he ate his breakfast and medicine each morning. Can’t wait to have Masheika back to stay with Leon! ☺️

Sitter Profile Image: Thalia M.
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Sitter Profile Image: Thalia M.
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13.

Thalia M.

I’d love to care 4 your little one!
Chicago, IL, 60615
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$50
per night

I highly recommend Thalia! She cares for my dogs and she's always attentive, gentle and playful. Thalia does more than the minimum with my pets. She makes sure they're safe but she also helps keep them happy :) She has always been on time and showed up with a great attitude.

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
11 reviews
from
$72
per night

Nicole took care of our house and puppy for 10 days while we were traveling. She is amazing and truly loves and cares for dogs. She communicated really well with us while we were gone but also before we were leaving. She was very flexible to accommodate our travel schedule as well. We highly recommend her and will for sure book her again!

Sitter Profile Image: Chau T.
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Sitter Profile Image: Chau T.
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15.

Chau T.

Active sitter with huge yard
Englewood, Chicago, IL, 60621
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
2 repeat clients
from
$40
per night

Chau is such the animal whisper. Somehow animals gravitate to her, probably because she understands their boundaries and has a kind soul. I’ve been fortunate to watcher her raise her one year old pup. Her dog is so well behaved and confident, which speaks to the training Chau did with her. Chau is thoughtful and patient. Your fur baby will be in really good hands.

Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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16.

E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
240 reviews
103 repeat clients
from
$100
per night

Liz is a perfect candidate for being a dog sitter. She's great with animals and very conscientious. She's currently caring for our pet and I feel confident being away as I know he is getting lots of love and attention!

Sitter Profile Image: Logan T.
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Sitter Profile Image: Logan T.
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17.

Logan T.

Its a dog thing and we understand
Chicago, IL, 60609
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
1 repeat client
from
$40
per night

Logan is a great dog sitter! He does amazing with our puppy and is able to guide her to success. He is also helping us train her not to pull on walks! He is so sweet and caring to our dog. We definitely recommend Logan!

Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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18.

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
20 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: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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19.

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
23 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!

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Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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20.

Dee M.

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

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!

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Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Grand Boulevard:


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