House Sitting in New City, 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
5.3 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 incredible! He sent many updates, pictures, and kept our apartment so clean it was if no one stayed here! Our dog certainly isn’t the easiest to watch, but we felt comfortable the entire time due to how communicative Otis was. He is well experienced, and someone I recommend to anyone looking for a dog sitter!

Availability updated 2 days ago
Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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2. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
2.2 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

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!

Availability updated 19 days ago
Sitter Profile Image: Alexa B.
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Sitter Profile Image: Alexa B.
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3. Alexa B.

200ccs of love and affection = me
Chicago, IL, 60619
4.9 mi. away
House Sitting, Dog Walking
from
$50
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
Profile image

Alexa did a wonderful job taking care of our dog in our home over a long holiday weekend. She was communicative, made sure Beau got his walks and play time, left our home clean and our dog happy. She followed our instructions on everything and asked questions when she wasn’t sure about something. We hope our dog wasn’t too crazy for her, but we would gladly welcome her back! So grateful we found Alexa.

Availability updated 12 days ago
Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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4. Belicia K.

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

Belicia took wonderful care of Anya while we were away for 8 days. She fed and walked her and sent us numerous photos and updates. Anya fell sick during her stay and Belicia took great care of her. We would love to work with her again!

Availability updated 19 days ago
Sitter Profile Image: Deven S.
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Sitter Profile Image: Deven S.
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5. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5.0 out of 5 stars
57 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 26 days ago
Sitter Profile Image: Shakira C.
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Sitter Profile Image: Shakira C.
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6. Shakira C.

RoverGO
Rover 101
Your Pup is My Pup
South Shore, Chicago, IL, 60649
5.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5.0 out of 5 stars
41 reviews
7 repeat clients
Profile image

Shakira is amazing! I feel like she's part of the family. She did an amazing job looking after my Maltipoo, Dash! She sent plenty of pictures and videos throughout the day. I really appreciate the way she made both me and Dash feel comfortable. Before she left, I had already booked her for another sitting for Dash. She's the best!

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

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.0 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 took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.

Availability updated 7 days ago
Sitter Profile Image: Nicole R.
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Sitter Profile Image: Nicole R.
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8. 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 4 days ago
Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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9. Allison J.

Star Sitter
Previous Veterinary Technician
Chicago, IL, 60608
3.3 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 great with our two pups, as always. Very responsive with updates and leaves the house very clean. Our go-to any time we leave town!

Availability updated 30 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
4.8 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: Margo K.
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Sitter Profile Image: Margo K.
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11. Margo K.

Animal lover living in Bridgeport!
Bridgeport, Chicago, IL, 60608
2.3 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 today
Sitter Profile Image: Cristian S.
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Sitter Profile Image: Cristian S.
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12. Cristian S.

Star Sitter
Any Size, Any Breed, Count On Me
South Lawndale, Chicago, IL, IL, 60623
4.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
30 reviews
10 repeat clients
Profile image

Cristian is great. He is very caring and responsible. He took care of our two dogs very well. They love him. One of our dogs didn’t eat well and Cristian made sure he ate his meal. We had meet and great and Cristian took his time to pick up keys and go over the care instructions with us. He sent videos everyday and kept us update when he headed out to walk the dogs. We felt very peaceful during our trip knowing that our babies were in great care. Thank you!

Availability updated 45 days ago
Sitter Profile Image: Shiri B.
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Sitter Profile Image: Shiri B.
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13. Shiri B.

Star Sitter
Kind and practical pet lover
Englewood, Chicago, IL, 60621
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5.0 out of 5 stars
15 reviews
2 repeat clients
Profile image

Shiri was a wonderful house sitter who took loving care of our two large dogs, our home, and sent lots of photos of our fur babies. Would happily book with Shiri again!

Availability updated 5 days ago
Sitter Profile Image: Montserrat J.
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Sitter Profile Image: Montserrat J.
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14. Montserrat J.

Star Sitter
8 years of experience with pets
Brighton Park, Chicago, IL, 60632
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
Profile image

Montserrat was GREAT! She agreed to come over a few days before our booking to meet our squad, which we really appreciated. During her stay, she sent us many updates with tons of pictures! This was our first time using Roover and we were nervous but she quickly made us feel very comfortable about leaving. I would highly recommend asking Montse to watch your fur babies! I will definitely rebook with Montse for our next vacation.

Availability updated 14 days ago
Sitter Profile Image: Marisa C.
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Sitter Profile Image: Marisa C.
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15. Marisa C.

Experienced &Friendly Pet Caregiver
Chicago, IL, 60608
3.5 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 6 days ago
Sitter Profile Image: Andrea H.
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Sitter Profile Image: Andrea H.
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16. Andrea H.

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

My first time using Rover and will definitely reboot with Drea. She was an amazing sitter, she sent me a few pictures of my dog throughout his stay. She planned out the activities and made sure to confirm his diet. Overall had a great first experience.

Availability updated 3 days ago
Sitter Profile Image: Sarai O.
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Sitter Profile Image: Sarai O.
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17. Sarai O.

Reliable, trustworthy & loving!
Bridgeport, Chicago, IL, 60608
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5.0 out of 5 stars
16 reviews
6 repeat clients
Profile image

Sarai took great care of our apartment and of our cat, Cole! When we got back after a week-long trip away he was calm and happy. Sarai also sent us regular photos and videos and was very responsive over text. Would absolutely book again!

Availability updated 3 days ago
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
2.9 mi. away
Boarding, House Sitting, Doggy Day Care
from
$30
per night
5.0 out of 5 stars
24 reviews
8 repeat clients
Profile image

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!

Availability updated 13 days ago
Sitter Profile Image: Jillian A.
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Sitter Profile Image: Jillian A.
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19. Jillian A.

Your Go-To Gal for Pet Care!
New City, Chicago, IL, 60609
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5.0 out of 5 stars
45 reviews
25 repeat clients
Profile image

Jillian was great with our boy Jax! We got lots of updates and pictures and Jillian was extra kind checking in with us to see if Jax would enjoy extra activities with her and ensuring his week was comfortable and enjoyable. We had no stress about Jax on our vacation and he is looking forward to another visit with Jillian again soon!

Availability updated 20 days ago
Sitter Profile Image: Jennifer R.
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Sitter Profile Image: Jennifer R.
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20. Jennifer R.

Reliable Pet Care/Flexible Weekdays
Chicago, IL, 60609
0.8 mi. away
House Sitting, Drop-In Visits
from
$60
per night
1 review

Jen was a SAINT caring for my dog. Since my pet has special requirements, many caregivers aren't willing to accept, but Jen was ready for the challenge. From making him special meals to taking him on his long walks, she succeeded in this challenge.

Availability updated 8 days ago

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

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

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

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