House Sitting in Armour Square, 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
2.8 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

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!

Availability updated yesterday
Sitter Profile Image: Marty T.
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Sitter Profile Image: Marty T.
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2. Marty T.

Rover 101
Gold Coast Old Town
Near North Side, Chicago, IL, 60610
4.1 mi. away
House Sitting, Dog Walking
from
$25
per night
5.0 out of 5 stars
52 reviews
22 repeat clients
Profile image

Marty stayed with my dog over the holidays. He was communicative and respectful, leaving my house in great shape. He clearly cares for dogs, and my dog took to him right away. I really appreciated that Marty let me know about a plumbing issue (which he did not cause!) so I was able to get someone in as soon as I got home — being upfront inspires so much more confidence than any surprises. I would recommend Marty!

Availability updated 19 days ago
Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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3. Belicia K.

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

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.

Availability updated 18 days ago
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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4. Emily N.

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

I was very nervous as a first time Rover user and so happy I found Emily! She asked detailed questions about my dogs care and habits during our initial meet and greet which put me at ease, sent photo updates during her stay where he seemed very happy / comfortable with her and came home to a clean place. Would definitely book again!

Availability updated 18 days ago
Sitter Profile Image: Emily B.
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Sitter Profile Image: Emily B.
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5. Emily B.

Experienced Corgi dog mom!
Chicago, IL, 60661
2.7 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
13 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 5 days ago
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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6. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.3 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

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!

Availability updated 6 days ago
Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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7. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
1.7 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 25 days ago
Sitter Profile Image: Margo K.
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Sitter Profile Image: Margo K.
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8. Margo K.

Animal lover living in Bridgeport!
Bridgeport, Chicago, IL, 60608
1.1 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 4 days ago
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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9. Nicole R.

Lovable reliable & trustworthy!
Bridgeport, Chicago, IL, 60616
0.8 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 3 days ago
Sitter Profile Image: Nico M.
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Sitter Profile Image: Nico M.
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10. Nico M.

Caring for your pet like my own
Chicago, IL, 60611
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$69
per night
5.0 out of 5 stars
17 reviews
1 repeat client
Profile image

Nico was wonderful! He stayed in constant communication with us throughout his stay and provided us with plenty of good pictures of Huck. Our dog had a minor illness earlier in the week that required medication and Nico did a great job with making sure Huck took them on schedule every day. He took the time to learn Huck’s quirks, which we very much appreciate!! Will definitely be booking with Nico again!

Availability updated today
Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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11. Allison J.

Star Sitter
Previous Veterinary Technician
Chicago, IL, 60608
1.7 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 stayed with our pups for two nights and we couldn’t be happier! They were in great care, she paid attention to all of our notes, and the house was in impeccable order when we came home. She communicated daily and sent photos just so we could see how comfortable everybody was. We are all very happy with Allison and would book her again anytime!

Availability updated 29 days ago
Sitter Profile Image: Maritza V.
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Sitter Profile Image: Maritza V.
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12. Maritza V.

Longtime Doggie Sister
Near South Side, Chicago, IL, 60605
1.6 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 12 days ago
Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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13. Johnathan W.

Star Sitter
A friend that cares
Loop, Chicago, IL, 60642
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$125
per night
5.0 out of 5 stars
48 reviews
18 repeat clients
Profile image

Jonathan took such good care of our dog while we were away! They went on long walks and our dog looked super happy in every picture he sent. Jonathan sent descriptive updates and communicated as needed. We never worried about our pup while we were away. Thanks, Jonathan!

Availability updated 12 days ago
Sitter Profile Image: Courtney G.
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Sitter Profile Image: Courtney G.
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14. Courtney G.

Star Sitter
A connection like a second mother!
Loop, Chicago, IL, 60605
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$90
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
Profile image

Courtney was a life saver. We're new to Chicago and needed a last-minute sitter for a long weekend for our two high-energy large pups. Courtney came over the evening before we left to do a walk through, asked tons of questions, and sent lots of pictures while we were gone. The pups were well taken care of and smiling ear-to-ear when we returned. She's a little pricey comparatively, but worth it! Will be rebooking with her for future sittings.

Availability updated yesterday
Sitter Profile Image: Connor D.
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Sitter Profile Image: Connor D.
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15. Connor D.

Feline Fanatic, Canine Connoisseur
Near South Side, Chicago, IL, 60605
1.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$38
per night
5.0 out of 5 stars
22 reviews
4 repeat clients

Connor has always had a fantastic and real connection with animals! They warm up to her immediately. From our own pets to others who have witnessed her care, compassion and love with their pets, I wholeheartedly recommend Connor for this work. Your pets will be in amazing hands and will also thank you!

Availability updated 4 days ago
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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16. Emily L.

Rover 101
Pet passionate care😊🫶
Chicago, IL, 60616
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5.0 out of 5 stars
12 reviews
1 repeat client
Profile image

This was our first time leaving our dog with a sitter and he was in great hands with Emily. She was very communicative and went above and beyond with updates and pics. Our pup was very happy and obviously well cared for. We would definitely book again.

Availability updated yesterday
Sitter Profile Image: Andrea H.
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Sitter Profile Image: Andrea H.
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17. Andrea H.

Animal lover ❤️
Douglas, Chicago, IL, 60616
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
6 reviews

Awesome pet sitter for my dogs, they always love being petsit by her. She was patient, kind, and caring. She even taught them a few tricks! 10/10 recommend!!

Availability updated 2 days ago
Sitter Profile Image: Grayson T.
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Sitter Profile Image: Grayson T.
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18. Grayson T.

Can’t wait to meet your dogs :)
Lower West Side, Chicago, IL, 60608
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5.0 out of 5 stars
3 reviews
1 repeat client
Profile image

Grayson is awesome! Their professional experience with pets definitely shows. Especially when they navigate and meditate any of our pets’ little discrepancies. Their experience and understanding of animal behavior and social cues gives us a lot of peace of mind. I highly recommend Grayson for any of your pet care needs! You won’t regret leaving your pets in their very capable hands!

Availability updated 5 days ago
Sitter Profile Image: Annie X.
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Sitter Profile Image: Annie X.
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19. Annie X.

Rover 101
Your 1st kitty/doggy visit FREE ✔
Armour Square, Chicago, IL, 60616
0.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5.0 out of 5 stars
126 reviews
97 repeat clients
Profile image

Annie watched our French Bulldog, Fiona, for 7 days. It was also a holiday weekend which is a big deal. She did a great job with Fiona! She would send pictures and Fiona looked like she was in her element at home. I felt so comfortable with Annie taking care of Fiona that I didn't feel the need to check in constantly (which is a big thing for me). She also left the apartment just as clean as we had left it! She was great!

Availability updated 11 days ago
Sitter Profile Image: Karen P.
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Sitter Profile Image: Karen P.
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20. Karen P.

Rover 101
Walks and loving care for your pet!
Chicago, IL, 60616
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
3 reviews

Karen is great with dogs. I’ve worked along side her at a doggie daycare. We are in charge of watching up to 25 dogs at a time and reading the dogs body language for safe play. Some dogs were small while other are very large. But none that Karen couldn’t handle. She is devoted, kind, and gentle with all of the dogs here. I would trust her with my own babies.

Availability updated 9 days ago

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