Pet Sitting & Drop Ins In Near South Side 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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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
1.2 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
32 reviews
24 repeat clients
from
$22
per visit

Thank you so much for all the photos and updates! Baker was happy to have us home but with your care he was well looked after. If anyone is looking for a cat sitter I can highly recommend you as the affection and play time you give was well worth every penny. Thank you for taking care of our boy.

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Sitter Profile Image: Candice L.
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Sitter Profile Image: Candice L.
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2. Candice L.

Rover 101
Star Sitter
Medical Student & Animal Whisperer
Chicago, IL, 60605
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
100 reviews
37 repeat clients
from
$25
per visit

I couldn’t be happier with Candice! Her friendliness, attention to detail, and regular photo updates made my time away worry-free. My cat Waffle clearly adored her. During a family emergency, Candice's adaptability was a true lifesaver. Without a doubt, I'll be reaching out to her for future cat-sitting needs. Highly recommend!

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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
0.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
144 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!

Sitter Profile Image: Emily A.
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Sitter Profile Image: Emily A.
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4. Emily A.

Star Sitter
South Loop pet expert!
Near South Side, Chicago, IL, 60605
0.6 mi. away
Drop-In Visits
5.0 out of 5 stars
176 reviews
62 repeat clients
from
$20
per visit

Emily was great with our cats. Even our sweet, scared boy came right out to meet her and engaged in play time. She always came on time as scheduled and we’re hoping to book her for a longer trip we have coming this fall!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Anthony M.
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Sitter Profile Image: Anthony M.
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5. Anthony M.

Star Sitter
Gentle, Flexible and Caring!
Near South Side, Chicago, IL, 60616
0.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
216 reviews
50 repeat clients
from
$18
per visit

Anthony was great with Bella! He was responsive, sent photos, and always kept me updated with everything. I highly recommend booking with Anthony, I know I will in the future.

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

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
2.0 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 was amazing with my reactive border collie! She took her time introducing herself and helped Zuri be super comfortable on a walk when she’s not used to being taking out by others!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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7. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
118 reviews
36 repeat clients
from
$20
per visit

Emily did a great job with my cats! She was very attentive to their needs and spent a lot of time with them, and all of her communication was prompt and thorough. Highly recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Darcy P.
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Sitter Profile Image: Darcy P.
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8. Darcy P.

Ace Ventura for pets 🐶😻
Chicago, IL, 60605
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
161 reviews
84 repeat clients
from
$22
per visit

Darcy is awesome! She took great care of our cat Mochi in the past week while we are traveling. She sent us pictures and videos everyday, followed the instructions on watering plants etc and even took out our trash before she left! Thank you so much!

Sitter Profile Image: Jason C.
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Sitter Profile Image: Jason C.
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9. Jason C.

Star Sitter
Friendly dog walker from the UK
Loop, Chicago, IL, 60605
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
90 reviews
27 repeat clients
from
$18
per visit

Jason is such a wonderful asset for our family’s lifestyle! The pups love him, he’s flexible, extremely communicative and dependable! There’s a reason he has so many Rover clients, he’s the best!

Sitter Profile Image: Grace T.
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Sitter Profile Image: Grace T.
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10. Grace T.

Dog Lover!
Loop, chicago, IL, 60605
0.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
30 repeat clients
from
$20
per visit

Grace has been a regular dog walker for us for a couple months now and we're really happy to continue working with her. She's professional, easy to communicate with, and does a great job spending time with our dogs. We appreciate her greatly. I would recommend her highly.

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Sitter Profile Image: Sylvia W.
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Sitter Profile Image: Sylvia W.
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11. Sylvia W.

Star Sitter
Flexible Schedule, cats and dogs!
Chicago, IL, 60605
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
7 repeat clients
from
$18
per visit

Sylvia always dropped in around the agreed upon time, took pictures, and gave detailed updates on how TC was doing. It was a great and easy experience and I highly recommend!

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

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

Abigail is a dependable, responsible, honest, and trustworthy person. Abigail is ball of sunshine that always knows how to brighten up the darkest of days. She is a hard worker and does an amazing job at the work that she does do. Abigail is dedicated to the things that she puts her determined mind up to. She is a great person that loves animals and will give them the best attention that every animal deservers.

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Sitter Profile Image: Mia M.
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Sitter Profile Image: Mia M.
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13. Mia M.

I love all animals big and small
Chicago, IL, 60607
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$20
per visit

mia is great! good communication throughout the drop-in and was very attentive to my anxious dogs requirements

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

Star Sitter
Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
0.1 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!

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

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
0.4 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 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Judy L.
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Sitter Profile Image: Judy L.
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16. Judy L.

Pawsitive Progress: Walk & Train
Chicago, IL, 60616
0.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per visit

My dog LOVES Judy. I think the world of her. Judy is reliable, honest. She clearly loves dogs & is wise in her care of them. I strongly recommend her for any task someone wants help with in giving their dog the best care possible.

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Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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17. Ann-Marie H.

Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
0.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$25
per visit

Ann-Marie was awesome with our very young puppy - highly recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Amy C.
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Sitter Profile Image: Amy C.
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18. Amy C.

Animal enthusiast with extra ♥️
Chicago, IL, 60605
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
3 repeat clients
from
$20
per visit

Amy was absolutely amazing with caring for our pets and their various needs. Very helpful, kind, and communicative. Couldn’t have asked for better care of our animals! Would highly recommend!

Sitter Profile Image: Julian K.
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Sitter Profile Image: Julian K.
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19. Julian K.

Star Sitter
Seasoned sitter who loves animals!
Near South Side, Lexington, IL, 60605
0.6 mi. away
Drop-In Visits
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$18
per visit

Julian was awesome! He was available when I was leaving town pretty last minute, made it easy to organize with him, and made it really easy to feel comfortable that Waldo would have plenty of care and attention! He sent great pictures and, my sometimes shy kitty, was happily playing immediately!

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Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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20. Rachel W.

Star Sitter
Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
0.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
42 reviews
17 repeat clients
from
$25
per visit

Rachel provided such great care of my cat Theo while I was away for a week! I really enjoyed receiving daily pictures and visit summaries. He must have had lots of fun with Rachel because he skipped the cuddles and was ready to play as soon as I got back!

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Drop-In Visits