Pet Sitting & Drop Ins In Armour Square

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

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Top rated Armour Square pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Ruari H.
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Ruari H.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Bridgeport, Chicago, IL, 60616

Amazing as always

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Che R.
Sitter Profile Image: Eunice Y.
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Eunice Y.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
59 reviews
27 repeat clients
4 years of experience
Loop, Chicago, IL, 60607

Eunice was so kind and jumped in to watch Goonie very last minute. I appreciated her updates and how she was kind enough to clean up his messes!! Looking forward to working with her again!!

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Kate S.
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
7 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine was great! She was patient with my sassy cat and very communicative with me while I was on vacation. Would definitely use Nadine in the future.

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Stephanie D.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$17
per visit
5.0 out of 5 stars
26 reviews
12 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Joselin was so kind and responsive. He took care of my sweet baby cat for two days very well. She is so communicative! She sent a lot of photos and videos of my cat. Highly recommended.

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Nargess H.
Sitter Profile Image: Hallie B.
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Hallie B.
from
$17
per visit
5.0 out of 5 stars
29 reviews
6 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Hallie did a great job on a last minute request. She provided great updates about my girls and even let me know that my sink wasn’t draining! I will definitely book with her again.

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Sarah B.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$22
per visit
4.9 out of 5 stars
52 reviews
10 repeat clients
21 years of experience
Bridgeport, Chicago, IL, 60616

Sarah is professional, caring, and communicative and gave regular updates which I really appreciated. My cat was totally relaxed when I got home. Sarah is my new go to cat sitter!

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Zoe A.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was a fantastic rover for our dog! She was extremely responsive, punctual, and helped us several times on short notice! She also clearly cared for our dog and was super kind. Would recommend her to anyone!

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Libby R.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
24 reviews
10 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Daphnay was amazing! She was always on time for twice daily check-ins. She played with Bleu as well as took him on runs. She is really reliable and very trustworthy. Can’t wait to book her again.

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Eric T.
Sitter Profile Image: David K.
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David K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
154 reviews
49 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60616

Second time using David -he’s great! Very timely and leaves the place so clean. Really appreciate how well he looks after August and takes care of his spaces and my home. Booked him for another trip already!

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Joshua H.
Sitter Profile Image: Namira J.
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Namira J.
Star Sitter
from
$19
per visit
4.9 out of 5 stars
41 reviews
16 repeat clients
10 years of experience
Chicago, IL, 60616

This was Namira's second time watching my elderly dog, who added two pills since our last visit, and has been starting to struggle with joints. She was engaged and made sure to check in with me when he was potentially having a bad day so I could evaluate and I could feel confident he was in good hands once again.

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Brittany E.
Sitter Profile Image: Jason C.
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Jason C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
58 reviews
17 repeat clients
15 years of experience
Chicago, IL, 60616

Jason is absolutely INCREDIBLE with my two cat gals. He plays with them when they are missing me and is SO accommodating. I trust Jason with my fur babies and always reach out to him first if I am out of town. Tomato and Elphie love you, Jason! Thanks for being amazing.

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Abby D.
Sitter Profile Image: Annie X.
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Annie X.
from
$28
per visit
4.9 out of 5 stars
156 reviews
113 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

Annie did such an amazing job watching our 3 cats! She was very easy to communicate with and our cats seemed very happy when we got home! 100% recommend

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Kelsey T.
Sitter Profile Image: Nataliia S.
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Nataliia S.
Star Sitter
from
$21
per visit
4.9 out of 5 stars
27 reviews
13 repeat clients
2 years of experience
Chicago, IL, 60608

Great walker! Very reliable, punctual, and caring. My dog was happy and well taken care of, and I really appreciated the updates and photos during the walk. You can tell they genuinely love animals and treat them with care. I would definitely book again and highly recommend!

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Max K.
Sitter Profile Image: Angela E.
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Angela E.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
56 reviews
4 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

About: Up until recently I had a large reactive dog. She was my best friend and taught me not only patience, but also taught me so much about dogs. I wfh and am looking to add a little something to my schedule. I would love to give your dog the exercise it needs while you’re at work. I am willing to work with reactive dogs in case by case basis. I am also a dog walking volunteer at CACC. I wfh and have flexibility in my schedule. I am available afternoons and evenings m-f and can work something out on weekends if it was needed. I would take care of your animals at your home based on instructions you give me for you pet. I respect you as an owner and your pet and do not want to give overstep and boundaries

Sitter Profile Image: Isabel K.
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Isabel K.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
12 reviews
4 repeat clients
2 years of experience
Loop, Chicago, IL, 60605

Isabel is awesome and very consistent. My dog gets a little anxious at times and she established a routine that he absolutely loves. Highly recommend!

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Gracelyn F.
Sitter Profile Image: Julianne F.
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Julianne F.
from
$25
per visit
5.0 out of 5 stars
105 reviews
29 repeat clients
30 years of experience
Lower West Side, CHICAGO, IL, 60616

Julianne sat for our cat during a recent vacation. We'd recently brought a sweet, lovable stray cat into our home and were worried about finding the right cat sitter who would care about our Callie as much as we did. We met a few cat sitters and Julianne was the only one who offered ideas for ways to make Callie feel more comfortable while we were gone. One of the suggestions was scheduling youtube bird shows to come on the tv during the day. Callie LOVED this! So much so that even after we returned from vacation, Callie would look up at the tv screen expecting for birds to appear….well of course as any good cat mom would do, I put the birdies on for her! I appreciated Julianne's thoughtfulness and true desire to engage with Callie on her terms ;) We will definitely be working with Julianne in the future.

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Carrie C.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$22
per visit
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Tim is amazing! He was very communicative, prompt and most importantly patient and showed my fur baby the attention she needed when I was on vacation.

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wu p.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
from
$17
per visit
5.0 out of 5 stars
19 reviews
15 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

About: • Lifelong pet owner with hands-on experience caring for dogs of all ages, breeds, and temperaments • Comfortable with feeding schedules, medication administration, and special dietary needs • Experience with crate training, basic commands, and leash manners • Knowledge of dog body language and signs of stress or illness • Confident with high-energy breeds and senior dogs alike • Able to handle multiple pets at once • Regularly walk dogs in safe, dog-friendly neighborhoods and parks • Provide both high-energy walks and relaxed strolls tailored to your dog’s needs • Keep dogs mentally stimulated through sniff walks and playtime • Familiar with using different harnesses, leashes, and walking tools • Keep your pets comfortable in their own home with regular check-ins and companionship • Maintain routines for feeding, potty breaks, and bedtime • Provide updates, photos, and videos so you always know your pet is in good hands • Water plants, bring in mail, and keep your home tidy while you’re away • Comfortable with litter box cleaning, feeding, and playtime • Experience with shy or anxious cats—patient and gentle • Can care for small pets like rabbits, hamsters, or birds I’m available any day and time that works best for you—except Sunday mornings. On Sundays, I’m free after 3:00 PM. Whether you need early morning walks, mid-day drop-ins, or evening snuggles, I’ve got you covered! When caring for pets in my client’s home, I do my best to keep their routine consistent so they feel safe and comfortable. I follow all feeding, walking, and medication instructions carefully, and make sure they get plenty of attention, playtime, and affection. I respect the home, clean up after the pets, and always keep you updated with messages and photos so you have peace of mind. If I’m caring for pets in my own home, I make sure they have a clean, cozy space to relax and feel at home. I provide regular walks, playtime, and cuddle sessions. I also pay close attention to how they’re adjusting to a new environment and take extra care to make them feel calm, loved, and secure. Whether your pet is high-energy or low-key, I adjust to their needs and treat them like family.

Sitter Profile Image: Andres G.
Verified Enhanced Background Check
Andres G.
from
$13
per visit
5.0 out of 5 stars
28 reviews
10 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60608

Andres took good care of my two cats; they looked happily fed and were sitting nicely in all the pics! He was also flexible with timing, which I appreciated.

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Khami Z.
Sitter Profile Image: Paola T.
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Paola T.
from
$20
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
7 years of experience
Chicago, IL, 60608

About: I’ve had dogs since I was a kid, i had a Yorkshire Terrier, and a Shitzu. I’ve been relied upon by family to feed, walk and bathe their dogs when they’re out of town. I’m currently working full time, giving me plenty of extra time in the day to take care of doggies and kitties around town. Send me a message, and I'll respond a promptly as possible. I will treat your fur baby as I treat my own. I’ll make sure they have water, play with them, cuddle, and I'll make sure they get their steps in for the day.

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Over 37
pet parents in Armour Square have booked pet sitting

Armour Square pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Gabby was kind and professional, making organizing her visits a breeze. We would book with her again and recommend her for others, especially if you live nearby!

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David K.
Drop-In Visits
5.0 out of 5 stars

Samira is always very communicative and sends cute photos! She has always followed any instructions and is very reliable. We have used her services more than once and would highly recommend her. She's the best in the area!

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Taissa L.
Drop-In Visits
5.0 out of 5 stars

Mairead is the best cat sitter! Howie and Gus looked forward to their daily visit. Mairead treated them like her own cats and it brought so much comfort while we were out of town. Thanks Mairead!

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Jolyn H.
Drop-In Visits
5.0 out of 5 stars

Absolutely fantastic sitter for our four kitties! She went above and beyond. It’s very clear she’s putting her whole heart into taking care of the fur babies. She stayed with them not just to feed and water but to play and brush, even bringing her own toys! Would rebook in a heartbeat.

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Aimee K.
Drop-In Visits
5.0 out of 5 stars

Ella is amazing! Biscuit absolutely loves her, and I really appreciate how communicative she is after every walk. What sold me completely was during a terrible thunderstorm, Ella still showed up and even took extra time to calm Biscuit down since he gets so nervous during storms. That kind of care says everything about who Ella is. We feel so lucky to have her walking our Maltipoo and recommend her without hesitation.

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Alison H.
Drop-In Visits
5.0 out of 5 stars

Samia was fabulous once again! Can’t recommend her enough. Very communicative. Great videos. And even offered to bring in stuff before a storm. Our shy kitten LOVES her! And she’s super understanding when my older cat acts up. She leaves a different movie on for the girls before she leaves lol that’s my favorite.

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Callie J.
Drop-In Visits
5.0 out of 5 stars

Diana is wonderful!!! She is so trustworthy and sends great videos of my cat having fun while I’m away. Highly recommend!

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Raven R.
Drop-In Visits
5.0 out of 5 stars

Rachel was great! She was able to drop in and check on our cat for a few days for a reasonable price. Would recommend!

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Erin V.
Drop-In Visits
5.0 out of 5 stars

Andres took good care of my two cats; they looked happily fed and were sitting nicely in all the pics! He was also flexible with timing, which I appreciated.

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Khami Z.
Drop-In Visits
5.0 out of 5 stars

Paola took such great care of Luna! Even before our scheduled drop-in dates, her communication was quick and responsive, and she kept me updated throughout all five visits. I felt very comfortable knowing Luna was in such good hands while I was away. I loved receiving the updates and photos from each visit. Luna was well cared for and got plenty of attention during every drop-in. :) I would absolutely book with Paola again and highly recommend her to anyone looking for a trustworthy and caring pet sitter!

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Bianca C.
Drop-In Visits
5.0 out of 5 stars

Kayla was such a phenomenal sitter for my cat Albert! I highly recommend for attentive service and great care.

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Margaret P.
Drop-In Visits
5.0 out of 5 stars

Sam took great care of my quite rambunctious 3 month old puppy and unfortunately gad to endure one of her bouts of zoomies. I would definitely recommend him.

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Jim M.
Drop-In Visits
5.0 out of 5 stars

Ruari was very responsive and sent photos to make certain to me that everything was good for our pet. Would recommend to anyone

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Will B.
Drop-In Visits
5.0 out of 5 stars

I had a last minute weekend trip and Vitaliia was great at getting back to me quick saying she can stop in and feed my cat! Great communication & quick response!

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Lindsey L.
Drop-In Visits
5.0 out of 5 stars

Christina did a great job taking care of my five cats, two of whom zi have medical needs. I really appreciated her daily updates and photos of my boys.

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Susan B.
Drop-In Visits
5.0 out of 5 stars

Maya took great care of both my indoor and outdoor cats while I was away. She was in regular communication with me about whether or not the cats were visible during her drop-ins, as well as how open they were to getting some rubs and TLC. She even brought my dumpsters back into my yard on trash day and made sure packages delivered to my home made it safely inside. Maya is a sweetheart and I absolutely plan on having her care for my babies for my next extended out of town trip!

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Erica M.
Drop-In Visits
5.0 out of 5 stars

Dominick took great care of my cat while I was out of town! She's very responsive and I appreciated all the photos and updates given.

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Lily L.
Drop-In Visits
5.0 out of 5 stars

Morgan provided excellent care to Francie and Neeley while I was gone. I came home to two cats who, while they missed me, were happy and content. Thank you!

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Mandy J.
Drop-In Visits
5.0 out of 5 stars

Anna was so caring and loving with my cats! She was incredibly patient and interacted at the comfort level of each cat. They immediately likened to her, and she went out of her way to keep my place orderly.

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Nugeen A.
Drop-In Visits
5.0 out of 5 stars

My cat absolutely loved Ashley! She came on schedule and I enjoyed looking at the drop-in report cards. I feel confident in booking her again.

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Luis C.
Drop-In Visits
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How Rover works

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

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  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!

The median cost per night for pet sitting in Armour Square is $20

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

Sitters in Armour Square average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Armour Square on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Armour Square pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 12,230 pet sitters in Armour Square. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 86% of Armour Square pet sitters respond in under an hour.

Pet sitters in Armour Square have an average of 14 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Armour Square.

Rover makes it easy to find Armour Square pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 12,230 pet sitters in Armour Square on Rover, so you’re sure to find the perfect match for your pet! In Armour Square, 96% of pet sitters offer daily exercise, 95% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.