House Sitting In Lower West Side Chicago

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Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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1. Otis B.

Dog's Best Friend
Loop, Chicago, IL, 60602
3.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5.0 out of 5 stars
65 reviews
28 repeat clients
Profile image

Otis was WONDERFUL. We couldn't have higher praise for him. We originally had another Rover scheduled for boarding, and she canceled on us 3 hours before we were supposed to head to the airport. Otis helped us last minute and arrived right on time to save us. Our Bernese Mountain Dog puppy is a highly energetic handful, and Otis kept her entertained and stimulated the entire weekend. Our dogs loved hanging out with him, and he was great about sending us picture updates throughout the day. The house was also in even better condition than when we left it. Otis was the best dog sitter and house guest, and we would 100% always book him if we could.

Availability updated today
Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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2. Lindsay J.

Star Sitter
Cat mom and animal lover
Chicago, IL, 60642
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$63
per night
5.0 out of 5 stars
56 reviews
13 repeat clients
Profile image

Lindsay did a great job taking care of our cats over the holidays. She was communicative, friendly, and most importantly, the cats liked her. Thank you, Lindsay!

Availability updated today
Sitter Profile Image: Pablo V.
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Sitter Profile Image: Pablo V.
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3. Pablo V.

Rover 101
Star Sitter
Fun walks
Chicago, IL, 60642
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$66
per night
5.0 out of 5 stars
272 reviews
103 repeat clients
Profile image

Pablo is wonderful. He is prompt, communicates well, and has great ease around dogs. Our pup is a rescue with a lot of quirks. Pablo took his time to get to know Leslie and is on his way to being her good friend.

Availability updated 2 days ago
Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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4. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
56 reviews
16 repeat clients
Profile image

Deven was professional and responsive from the first time I reached out to schedule a dog sitter. He was great both my puppy and older dog and comfortable providing oral, topical, and injection medications for my dog. Would highly recommend his services and will definitely be using again.

Availability updated 22 days ago
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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5. Emily N.

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

This was the first time we've had someone stay in our home to watch our dog while we were away and Emily was wonderful! She was very attentive to his needs and was able to manage his anxiety meds and special diet. We really appreciated all the photos and detailed updates every day! I would certainly recommend Emily!

Availability updated 16 days ago
Sitter Profile Image: Megan M.
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Sitter Profile Image: Megan M.
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6. Megan M.

Tell your dog I say hi
West Town, chicago, IL, 60614
3.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$70
per night
5.0 out of 5 stars
16 reviews
7 repeat clients
Profile image

Megan is one of the best sitters we have had! She was so patient with our slow to warm up dog and kept us fully updated with pictures while we were out of town! We normally hear that our dog is stressed and upset when we are out of town but I could tell even from the photos that our pup was totally comfortable with Megan and was doing great! We will definitely have her back again!

Availability updated 2 days ago
Sitter Profile Image: Alina K.
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Sitter Profile Image: Alina K.
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7. Alina K.

Star Sitter
Great company for your fluffy ones
West Town, Chicago, IL, 60622
3.4 mi. away
House Sitting, Dog Walking
from
$60
per night
5.0 out of 5 stars
27 reviews
11 repeat clients
Profile image

Alina did such a great job dog sitting for us this past weekend! She listened attentively to care instructions and sent us photos of our dogs, leaving us feeling assured that our dogs were being well taken care of.

Availability updated yesterday
Sitter Profile Image: Alison F.
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Sitter Profile Image: Alison F.
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8. Alison F.

Your animal's new best friend!
Near North Side, Chicago, IL, 60611
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
7 reviews
1 repeat client
Profile image

Had a great experience with Alison! She was sweet, super communicative, and very punctual. My two small dogs loved her, and I felt completely at ease. Highly recommend!

Availability updated 3 days ago
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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9. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
27 reviews
6 repeat clients
Profile image

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 ?

Availability updated 4 days ago
Sitter Profile Image: Emily B.
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Sitter Profile Image: Emily B.
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10. Emily B.

Experienced Corgi dog mom!
Chicago, IL, 60661
2.5 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
11 reviews
2 repeat clients
Profile image

Emily was awesome and so sweet! She sent lots of updates and pictures (which were requested) and Murphy was obviously having a great time and very comfortable with her. So thankful we found her! (:

Availability updated 2 days ago
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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11. Nicole R.

Lovable reliable & trustworthy!
Bridgeport, Chicago, IL, 60616
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
Profile image

This our first time hiring someone to take care of our dogs, usually we leave them with family. This time the entire family was on a trip so we opted for Rover and feel very blessed to have found Nicole. Nicole is very detail-oriented, communicated perfectly and even sent videos twice a day. We decided to leave the dogs at home instead of sending them to an unknown environment. And she not only walked them. She sat with them and gave them attention. This all became very crucial because it was very hard for me to leave my dogs this time around. One of my dogs had a bit of an eye irritation and she did a great job keeping track of his progress and keeping me updated. We are very grateful for Nicole and will definitely ask for her services again in the future.

Availability updated today
Sitter Profile Image: Ann Marie M.
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Sitter Profile Image: Ann Marie M.
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12. Ann Marie M.

Star Sitter
In a bind? I’d love to help!
West Town, Chicago, IL, 60482
2.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$90
per night
5.0 out of 5 stars
94 reviews
35 repeat clients
Profile image

Ann Marie was a wonderful sitter with Smitty and Scout. She was interested in learning the details of their care, took time to get to know them, and made me feel confident that our dogs were in good hands while we were away. She was very easy to communicate with and sent lots of pictures during the stay. She was great! We will ask her to sit again!

Availability updated 2 days ago
Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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13. Allison J.

Star Sitter
Previous Veterinary Technician
Chicago, IL, 60608
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$85
per night
5.0 out of 5 stars
63 reviews
24 repeat clients
Profile image

Allison was fantastic! This is the first time we’ve used Rover for in-house sitting and Allison put our minds at ease right away at our meet & greet. We love that she has extensive experience as a vet tech and felt comfortable leaving both of our dogs (one that can be pretty anxious and take a bit to warm up) in her care. She was flexible, communicative and kept us updated with texts and photos during her stay. Also left the house super clean. Looking forward to booking again!

Availability updated 27 days ago
Sitter Profile Image: Margo K.
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Sitter Profile Image: Margo K.
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14. Margo K.

Animal lover living in Bridgeport!
Bridgeport, Chicago, IL, 60608
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
4.0 out of 5 stars
7 reviews
Profile image

Margo did a great job. She was flexible and responsive. She sent lots of pictures and updates of our cats. We returned home after a week-long vacation and the house was in excellent shape. I will definitely use her for house-sitting and drop-in services in the future.

Availability updated yesterday
Sitter Profile Image: Minju Y.
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Sitter Profile Image: Minju Y.
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15. Minju Y.

I love paws 🐾
Chicago, IL, 60607
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
2 reviews

Kendall was amazing! Always sent updates and pictures of my dog whenever I asked. Was very attentive and caring as well! Definitely worth booking. She's really sweet and a fun gal to leave with your pet!

Availability updated 3 days ago
Sitter Profile Image: Marlena H.
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Sitter Profile Image: Marlena H.
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16. Marlena H.

Star Sitter
Shelter-animal trained pet sitter
Near West Side, Chicago, IL, 60607
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
37 reviews
11 repeat clients
Profile image

Marlena was flexible and responsive. Our dog was relaxed when we returned home later than scheduled and it was apparent that he had fun hanging out with her. We hope to be able to schedule her for dog sitting again in the future!

Availability updated 2 days ago
Sitter Profile Image: Maritza V.
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Sitter Profile Image: Maritza V.
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17. Maritza V.

Longtime Doggie Sister
Near South Side, Chicago, IL, 60605
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
Profile image

Maritza was amazing!! She sent updates on how our puppy was doing and she was very responsive overall. Highly recommend!

Availability updated 9 days ago
Sitter Profile Image: Corbin M.
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Sitter Profile Image: Corbin M.
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18. Corbin M.

Pet lover
Lower West Side, Chicago, IL, 60608
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
2 reviews

Corbin watched my dog for me while I was on vacation for a week. I have a shepherd mix, so he’s a larger dog, and corbin did great with him. He made sure to communicate with me to let me know that my dog was being taken out, fed, and cared for. 10/10 experience.

Availability updated 3 days ago
Sitter Profile Image: Jade T.
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Sitter Profile Image: Jade T.
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19. Jade T.

Highly experienced animal caregiver
Lower West Side, Chicago, IL, 60608
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
5 reviews
Profile image

Jade did a fabulous dog sitting Dobby. This is the first time I’ve used River and Jade could not have been better. She was happy to be with him, sent photos and kept the house spotless! A great find.

Availability updated 3 days ago
Sitter Profile Image: Marisa C.
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Sitter Profile Image: Marisa C.
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20. Marisa C.

Experienced &Friendly Pet Caregiver
Chicago, IL, 60608
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
Profile image

Marisa was great! She very naturally got along with my Paulie who admittedly can be uncooperative to say the least. 10/10

Availability updated 3 days ago

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  2. 2. Meet & Greet

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    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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