Pet Sitting in Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Niko F.
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Sitter Profile Image: Niko F.
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1. Niko F.

Star Sitter
Ensuring your pets safety/happiness
Lower West Side, Chicago, IL, 60616
0.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
24 repeat clients
from
$22
per visit

Niko was attentive and sent detailed messages regarding his visits with my pet. He took good care of my car. I would highly recommend his services!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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2. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$21
per visit

Crystal is amazing! She was very communicative, punctual, and the kitties seemed happy and well fed when we got back. I would absolutely book again!

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Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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3. Shimmy G.

Star Sitter
I love my pups & I’ll love yours!
Near South Side, Chicago, IL, 60605
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
141 reviews
27 repeat clients
from
$20
per visit

Shimmy is wonderful with my pup! She gives him lots of great play time and takes great photos. I trust that he is in good hands when Shimmy comes over!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Abigail R.
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Sitter Profile Image: Abigail R.
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4. Abigail R.

Here to care like their my own!
Loop, Chicago, IL, 60606
2.4 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$10
per visit

As a lifelong pet owner, Abigail possesses a wealth of experience in dealing with pets, and she is very caring and attentive to their needs.

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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
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
117 reviews
36 repeat clients
from
$20
per visit

Emily was so great with our cats! She always sent photo updates along with her check-in messages and she was flexible and able to come out again when the automatic feeder got jammed. I would definitely recommend Emily’s services and happily rebook her as a cat sitter!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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6. Michael D.

Star Sitter
Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
2.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
10 repeat clients
from
$20
per visit

Michael was easy to work with and it really seems like he enjoys spending time with animals. Any pet would be in good hands with him. Will definitely be in touch with him again!

Confirmed availability: Memorial Day Weekend
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
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$23
per visit

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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8. Otis B.

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

Otis has been quick to respond and super communicative. He clearly loves dogs and is attentive and patient with our fearful dog, which we really appreciate. So glad to have found him!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lisa H.
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Sitter Profile Image: Lisa H.
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9. Lisa H.

Star Sitter
Extended family to your fur babies
Loop, Chicago, IL, 60607
1.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$20
per visit

I was very happy to find Lisa, she is a true dog lover and takes amazing care of my fur baby “Luna”. Lisa will text over a picture, leave me information on treats that are best formy pets, and cares for each of them ,the way I would. I never worry about Luna when Lisa is around. Thank you so much for giving me "Peace of Mind" while I'm working!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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10. David K.

Star Sitter
Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
79 reviews
34 repeat clients
from
$25
per visit

David was absolutely wonderful. Went above and beyond any rover sitter we have worked with, who were also great! He was incredibly kind and considerate with our pet and with our home. We highly highly recommend David for any of your pet’s needs!

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Sitter Profile Image: Nicole K.
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Sitter Profile Image: Nicole K.
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11. Nicole K.

Pet Loving College Student
Chicago, IL, 60608
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$15
per visit

1st time away from my kids for more than two nights & also this was my 1st time using Rover. Anxiety is running super high but everything went off without a hitch. Nicole was extremely professional an took great care of my kids! I will be using Rover & hoping that I can book Nicole again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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12. Ashleigh H.

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$17
per visit

Ashleigh is the perfect sitter. She's responsive and reliable. My dog is shy and she's able to build his trust. I am so happy to have her as my sitter 😊

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Sitter Profile Image: Monica & Calvin M.
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Sitter Profile Image: Monica & Calvin M.
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13. Monica & Calvin M.

Rover 101
Your fur baby's new best friends!
Lower West Side, Chicago, IL, 60608
1.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
257 reviews
104 repeat clients
from
$25
per visit

Monica and Calvin took great care of my cat, spending lots of quality time with him and giving him lots of brushes, even cleaning the litter box when I didn’t specifically ask for it! I would definitely choose Monica and Calvin any time I needed someone to take care of my pets again. Lovely people!

Sitter Profile Image: Jessica F.
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Sitter Profile Image: Jessica F.
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14. Jessica F.

Star Sitter
Compassionate Behavior Specialist
Chicago, IL, 60607
1.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
57 reviews
18 repeat clients
from
$30
per visit

Jessica was absolutely amazing with our cats. She was extremely efficient with communicating during check ins and caring for their needs. I will definitely book with her again.

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Sitter Profile Image: Amanda J.
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Sitter Profile Image: Amanda J.
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15. Amanda J.

Star Sitter
Graduate student who loves animals!
Chicago, IL, 60607
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
11 repeat clients
from
$25
per visit

Amanda was wonderful! Very good with my kitty, responsive, and kind. AND she was able to pick up another day when my other sitter bailed. I’m so glad to find her!

Sitter Profile Image: Kristi T.
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Sitter Profile Image: Kristi T.
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16. Kristi T.

Rover 101
Ready to swap secrets w/ your pets!
Chicago, IL, 60608
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
34 reviews
11 repeat clients
from
$20
per visit

Kristi was fantastic! She really made my little Monty feel loved while I was away. I could see it in the many pictures and videos that she sent me. She showed up on schedule and let me know if she needed to deviate. She did an all around great job with feeding, medication, and cuddling. I would hire her again and recommend her to others without reservation.

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Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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17. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
1.0 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
$22
per visit

Sujae is an excellent cat sitter. She came for drop in visits on time and consistently over multiple days. I liked seeing pictures of all the cats and the nice notes she left. She helped me out of a jam when another sitter cancelled my pet sitting while I was already out of town. Rover helped me find Sujae and I’m super happy we found each other! Sujae did a wonderful job for me and my cats. Thanks Sujae!

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Sitter Profile Image: Ericka J.
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Sitter Profile Image: Ericka J.
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18. Ericka J.

Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$25
per visit

Ericka helped us while we were on vacation by checking on our cat, making sure she had fresh food/water and a clean litter box. She sent us pictures of our kitty and gave us updates at every check-in. Would definitely recommend her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Julianne F.
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Sitter Profile Image: Julianne F.
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19. Julianne F.

Nurturing Care Giver & Animal Lover
Lower West Side, CHICAGO, IL, 60616
0.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
75 reviews
21 repeat clients
from
$23
per visit

She’s amazing! We always get the most thorough report card for our two babies and she recently watched both of our cats for a week while we were out of the country and she arrived twice a day at the time we requested and sent lots of pics and played with our fur babies in the most fun and loving way! We felt 100% at ease having her here and that our cats were well taken care of! Forgot to mention one of our cats is senior and needs meds and lots of love and she was always in amazing shape and cared for when we returned…not stressed at all, which never happens after long times away! We will continue to use Julianne and are so grateful for her!

Sitter Profile Image: Jeff O.
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Sitter Profile Image: Jeff O.
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20. Jeff O.

Star Sitter
Caring, reliable pet sitting
Lower West Side, chicago, IL, 60608
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
60 reviews
19 repeat clients
from
$25
per visit

Jeff did a wonderful job with my 4 cats. I was really nervous leaving them alone with a stranger, but from the beginning he was very responsive and communicative. When he came by for the meet and greet it was clear he was a cat lover, and took the time to get to know my cats individually. I left him very complicated instructions (4 cats, 4 different diets, all 4 needed medicines), and he handled it like a pro. He sent me a ton of updates, photos and videos, and it was clear he put a lot of time into playing with them, petting them, bonding with them... I felt like I was able to relax and enjoy my vacation because they were in good hands. Highly recommend him!

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Chicago Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Chicago are rated on average 5 out of 5 stars based on 7,553 reviews.

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Rover.com is the simple, savvy way to find and book Chicago house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Chicago on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes the Rover Guarantee, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 300,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Chicago, IL house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

Drop-In Visits