Personalized care for your dog or cat - Armour Square

Highly-rated overnight sitters - Armour Square

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

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Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was fantastic and our pup clearly loved spending the weekend with her! She took her to play fetch every day and was flexible with us on our return home. 10/10 would recommend!

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Robert M.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
135 reviews
28 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

Ann is so great! My pup seemed to love his stay and she was great about sending daily updates and pics. Would definitely book with her again!

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Julian C.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
194 reviews
71 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley and her daughter treated our dog as if she was their own! Regular updates made me feel so confident that she was well taken care of. No issues with the other dogs she had in her care that weekend either. Will definitely book again!!

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Meg B.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
28 reviews
12 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.

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Tiffany S.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was phenomenal!! 5 out of 5 stars doesn’t even begin to cover it. So easy to communicate with, we received more pictures then we knew what to do with, and she was consistently taking the dogs on walks, to the beach, and out for treats. Couldn’t be more thankful. If we are ever in Chicago again we will be using her services!!

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Tony & Victoria B.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

I couldn't have asked for a better family to take care of my puppy while I was traveling. I could tell that the family truly enjoyed taking care of my dog Mac and gave him all the love and cuddles he is used to getting. Liz provided numerous pics and updates every day single day. I will definitely re-book the next time I travel! I would highly recommend Liz and family.

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Katie S.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

We planned our trip ahead of time and Bola made sure to keep open communication along the way. As we dropped our pup off to Bola, the transition was very easy. While Bola had Junie, Bola made sure to keep us updated with pictures. Thanks Bola

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Sean O.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
201 reviews
77 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

Nathan has taken care of our Luna twice now, both times on short notice, and we couldn’t be happier with him. He is incredibly caring, attentive, and truly treats Luna like his own. He kept us feeling completely at ease knowing she was in such good hands. The pickup and drop-off service is an added convenience that we really appreciate. We are so grateful to have found someone we trust and will definitely be using Nathan again in the future. Highly recommend!

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Juhi D.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Tim is a great guy who is amazing with animals. He provided pictures and updates every day. My dog did not even want to leave. He obviously provided great care and was very flexible with my schedule for pick up and drop off. I really appreciate his dedication and genuine love of animals.

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Daniel G.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$53
per night
5.0 out of 5 stars
96 reviews
22 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

Here’s a review you can leave for Jenna on the Rover app: We can't thank Jenna enough for taking such great care of our dog, Lola, while we were away for a family funeral. She went above and beyond, sending us daily pictures and updates that gave us peace of mind during a difficult time. When we missed our flight and needed to extend Lola's stay, Jenna was incredibly accommodating and flexible, which was a huge relief. Lola clearly loved her, and we could tell she was in the best hands. Jenna is sweet, reliable, and a true dog lover. I highly recommend her to anyone looking for a trustworthy and caring dog sitter! We will definitely be using her services again!

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Devina C.
Sitter Profile Image: Andre S.
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Andre S.
from
$50
per night
4.7 out of 5 stars
13 reviews
2 repeat clients
8 years of experience
Loop, Chicago, IL, 60605

Andre took amazing care of Howie during his stay!! Andre and his partner sent me updates and made me feel at ease while I was away! I will definitely recommend Andre to anyone!!

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Nadia S.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$40
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

Cassandra took great care of my dog Ace during his 4-day stay. I can tell he had a good time hanging out with her dog, Chewy. Cassandra was a pleasure to work with and I hope to use her services again for future boarding.

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Joseph G.
Sitter Profile Image: songen f.
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songen f.
Star Sitter
from
$55
per night
5.0 out of 5 stars
17 reviews
8 repeat clients
11 years of experience
Loop, Chicago, IL, 60605

Songen took excellent care of our toy poodle, Charley Charley got along very well with their maitipoo. Songen kept us updated with regular pictures, videos, and updates to calm our minds. Highly recommended.

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Neeraj S.
Sitter Profile Image: Jiayi G.
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Jiayi G.
from
$40
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Jiayi was awesome and I really appreciated all the pics and videos she sent! Perfect person for my firework anxious dog to spend the 4th with. Thank you so much Jiayi!

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Kristine P.
Sitter Profile Image: Ann-Marie H.
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Ann-Marie H.
Star Sitter
from
$55
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Loved the daily updates with pictures and videos. Made us feel comfy and happy that we booked with you. Also appreciated you taking him out to the dog park, playing with him inside, taking him on walks, and putting him in his crate for nap time/at night. Would book with you again! Thank you so so much for the great care!

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Izzy R.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$35
per night
5.0 out of 5 stars
24 reviews
18 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Cheyanne was amazing. She had great communication and my dog can be timid and not eat much at dog sitters but she didn't have that problem with her. Best sitter! Thank you

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Nicole M.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
363 reviews
99 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie is so amazing!! So flexible with timing, kind, and sends pictures! She also was so nice in meeting me before so I could make sure my dog would be okay with her dog. Her dog is so chill so it was perfect for my anxious dog. Thank you so much again Katie!!! Definitely will book again 😊😊😊

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Ana H.
Sitter Profile Image: MICHAEL C.
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MICHAEL C.
Star Sitter
from
$40
per night
4.9 out of 5 stars
48 reviews
6 repeat clients
25 years of experience
North Lawndale, CHICAGO, IL, 60623

Mike and Joanna were absolutely amazing! I needed last-minute care for my dog, and they responded almost instantly. From the start, they were friendly, professional, and incredibly accommodating. They took such great care of my dog and made the whole experience completely stress-free for me. It was clear that my dog was comfortable and well cared for the entire time. What really surprised me was that they even sent my dog home with free gifts — such a thoughtful and unexpected gesture, especially for such a short stay! I can’t recommend Mike and Joanna enough. If I could give them 10 stars, I absolutely would. Thank you both for going above and beyond!

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Chester A.
Sitter Profile Image: Andrea B.
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Andrea B.
Star Sitter
from
$57
per night
5.0 out of 5 stars
17 reviews
3 repeat clients
15 years of experience
Loop, Chicago, IL, 60607

Andrea took great care of my dog for 5 days and I had a really positive experience. Communication was great the whole time, she was very sweet, and my dog seemed like she had a great time with her. She was also super thoughtful and flexible, she even offered to do drop-off for me, which I really appreciated. She also noticed my dog was running low on food and reached out right away to ask if it was okay to ration it, which I appreciated because it showed she was paying close attention and wanted to make sure everything was handled properly. I would definitely book with her again!

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Zoe W.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
53 reviews
10 repeat clients
21 years of experience
Bridgeport, Chicago, IL, 60616

Sarah B was so nice and accommodating. This is the first time my pet has stayed with a sitter and my mind was completely at ease. Thanks Sarah!

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Anne S.
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Over 4.1 million
dogs curled up for a sleepover in a sitter's home on Rover1

Cat caregivers near you - Armour Square

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

1 / 1
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
39 reviews
7 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine was great with my cats! Super communicative and sent lots of pictures. Everything was clean and kept up with. Will definitely book with her next time I need a sitter!

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Natalie M.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$16
per visit
5.0 out of 5 stars
33 reviews
14 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: Chelsea G.
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Chelsea G.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
40 reviews
13 repeat clients
10 years of experience
Douglas, Chicago, IL, 60653

Chelsea did an amazing job caring for my kitties over the holidays! First, I ended up booking shorter notice and Chelsea responded immediately, was flexible, and was able to accommodate me and my babies. Chelsea was a great communicator when she was caring for my kitties, she gave consistent updates about how they were doing, as well as the tasks she completed when caring for them (refilling food and water, cleaning the litter box). I really appreciated the time and effort Chelsea put into caring for my babies, especially during the holiday time. Thank you!

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Eden A.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
53 reviews
10 repeat clients
12 years of experience
Bridgeport, Chicago, IL, 60616

Sarah was so amazing and helpful!! She sent frequent pictures of Luna and helped her (and me!) feel comfortable with our first time being apart from one another. Sarah, you rock!

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Skye G.
Sitter Profile Image: Hallie B.
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Hallie B.
from
$16
per visit
5.0 out of 5 stars
32 reviews
7 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: Angela E.
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Angela E.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
61 reviews
5 repeat clients
20 years of experience
Lower West Side, Chicago, IL, 60616

About: I have 2 cats at the moment. One is 9 and the other is 6. I have experience with senior cats as well. I have experience with almost everything except any sort of medical injections a cat may need.

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: Andres G.
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Andres G.
from
$20
per visit
5.0 out of 5 stars
37 reviews
14 repeat clients
2 years of experience
Lower West Side, Chicago, IL, 60608

Andres was great with my cat and was able to accommodate another week of visits when I had to extend my trip. He was proactive and made sure to check when her auto feeder was low and refill it.

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olga b.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$20
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: Kaylie L.
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Kaylie L.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
34 years of experience
Near South Side, Chicago, IL, 60616

Kaylie was excellent! She took care of my two cats for a week and did a great job! I got detailed daily updates with lots of great pictures. Kaylie was proactive about emptying the litter robot and was able to troubleshoot an issue with the feeders my cat use on her own. I would definitely book her again in the future!

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Lauren A.
Sitter Profile Image: Anastasiia M.
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Anastasiia M.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
163 reviews
38 repeat clients
17 years of experience
Near South Side, Chicago, IL, 60616

Anastasiia was a fantastic sitter. She provided lots of pictures and the cats adored her despite being shy at first. Would recommend to anyone!

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Benjamin F.
Sitter Profile Image: David K.
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David K.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
157 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: Kate W.
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Kate W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
119 reviews
38 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

Kate made me feel like I was letting my family watch my 3 cats. From first meeting to pickup she was stellar. i received pictures and video updates everyday along with verbal communication of how the cats were doing. She was also able to administer insulin shots which was a big plus. I have nothing to add comment wise for Kate to improve on. Everything was perfect. Thanks Kate!!!

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Martin C.
Sitter Profile Image: Annie X.
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Annie X.
from
$30
per visit
4.9 out of 5 stars
157 reviews
114 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: Chauntrell W.
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Chauntrell W.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
14 reviews
7 repeat clients
1 year of experience
Chicago, IL, 60616

Chauntrell is communicative and reliable. Would book again!

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Haden K.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$18
per visit
5.0 out of 5 stars
46 reviews
20 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60608

Jenna was a great sitter!! She took care of my fur kitty while away on holiday, made sure he got his food, tube treat and some play and cuddle time. She even helped bring in some packages that came for me. Very communicative, professional and easy going. Thank you!! Would hire again or recommend to others.

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Anna B.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
28 reviews
12 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Great with dogs! Daphne gave our 11yr old and 1yr old so much love and attention during her mid day drop in visits, we are grateful for her service. Wonderful and easy to work with and we will definitely use again.

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

Julianne was wonderful with our cat Amber, who has chronic kidney disease and needs special attention and medications. She was very comminicative, responsible, gave detailed reports and photos, and seemed to genuinely care for our kitty. Leaving Amber in Julianne’s care gave us a lot of peace of mind. Thanks again Julianne!

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Reyna P.
Sitter Profile Image: Namira J.
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Namira J.
Star Sitter
from
$17
per visit
4.9 out of 5 stars
42 reviews
16 repeat clients
10 years of experience
Chicago, IL, 60616

Such a good communicator and kind pet-sitter

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Ahmet K.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
24 reviews
18 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.

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Perfect for high energy dogs - Armour Square

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

1 / 1
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per day
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Timothy is our puppy’s favorite sitter (and ours too!). It’s clear he really understands and empathizes with dogs of all ages and sizes. We’ve had multiple stays at Timothy’s place, and every time our dog comes home happy, well-cared for and occasionally having made new dog friends! We especially appreciate the way he handles our rambunctious labrador puppy- calm, kind, and confident. It’s such a relief knowing she’s in good hands. We’re grateful to have found him, highly recommend!

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Eric F. R.
Sitter Profile Image: Annie X.
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Annie X.
from
$45
per day
4.9 out of 5 stars
157 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

About: ✦Limited spots left for July 4th weekend• South Loop/Downtown Providing calm, personalized care for every pet: Whether it’s in your home or mine, I provide calm, flexible, one-on-one care tailored to each pet’s personality and comfort level. From cozy boarding stays to in-home visits and overnight house sitting, your pets will always be treated with warmth and respect. 📍 Serving Chicago and surrounding suburbs — including Downtown, South Loop, West Loop, Bridgeport, Pilsen, Chinatown, Hyde Park, Lincoln Park, and beyond. Flexible travel options available, with customized arrangements for extended distances. 🐾 My Journey with Purrfect Pet Sit 🐾 Since 2019, I’ve provided trusted, professional pet care for busy Chicago professionals and families. With over six years of experience and many ⭐⭐⭐⭐⭐ reviews, I specialize in creating a stress-free, high-quality experience for both pets and owners. I specialize in cat sitting, small and medium breed, and senior pet care, with experience in administering oral and topical medications. I’m also open to caring for large dogs after a Meet & Greet, to ensure a good fit between each other. 🤝Meet & Greet Policy Meet & Greet is required for all new clients before confirming a booking. This step allows us to review care details, daily routines, home logistics, key access if needed, and overall fit in person, including how your pet and I interact. Scheduling details will be discussed during the inquiry process. 📸💬 Daily Photo & Text Updates You’ll receive regular photo and text updates, so you can travel or work with peace of mind knowing your furry family is happy and safe at my care. I can’t wait to meet your pets and make their time truly Purrfect! 🐾💛 🌞 Schedule & Availability I work full-time with a hybrid schedule in eCommerce, with some days onsite in the western suburb Lombard and others working from home in the city. Because I regularly commute and am comfortable with travel, I’m open to overnight house sittings and extended stays beyond my immediate area when everything is a good fit. 🐾 Drop-in visits: Available early mornings before work and/or evenings after work, depending on location and care needs. Exact visit times cannot be guaranteed, but I always aim to stay within a reasonable time window and will communicate updates as needed. Flexibility is required in terms of visit time. 🏠 House sittings: My standard rate covers overnight care from evenings through mornings and includes standard morning and evening potty walks, plus a final potty break before bedtime. Daytime hours, extended exercise walks, and constant care are not included in the base rate and may require additional fees depending on care needs and scheduling. 🚗Pick-up / Drop-off: Available upon request for repeat clients or when schedules align with my Lombard–Chicago commute route. 🐕 Boarding & daycare: Limited spots available - please message to confirm availability. 🏡 Home Environment & Safety Calm, cozy home with fenced yard and pet-friendly setup - a safe, peaceful space for every guest to relax, play, and rest comfortably during their stay.

Sitter Profile Image: Gabriel V.
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Gabriel V.
from
$33
per day
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Bridgeport, Chicago, IL, 60608

Gabriel was an excellent dog sitter for Walnut. He was attentive, patient, and very professional throughout the entire experience. He communicated clearly, provided updates, and always confirmed details, which gave me great peace of mind. Walnut seemed very happy and comfortable with him, and it was clear he genuinely enjoyed spending time with Gabriel. I truly felt that Walnut was in good hands. I would definitely recommend Gabriel and would love for him to continue sitting for us in the future.

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Mina R.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$30
per day
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$42
per day
5.0 out of 5 stars
194 reviews
71 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley was absolutely amazing! She went above and beyond to make sure that my dog was comfortable with his stay at her house while I worked. She was very communicative, made sure to have full understanding of his care, and gave him lots of love! From the moment I dropped him off, I can tell she really cares about the pets she and her daughter care for, when I picked Echo up at the end of the day, he was so sad to leave! I’ll definitely be booking with Ashley again! :)

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Maria C.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$45
per day
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was absolutely fabulous with my boy! Took him for a nice long walk. I could tell when I picked him up that he had really bonded with her.

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Isabel C.
Sitter Profile Image: Monica M.
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Monica M.
from
$35
per day
5.0 out of 5 stars
14 reviews
5 repeat clients
19 years of experience
Bridgeport, Chicago, IL, 60608

About: Hi! My name is Monica and I recently graduated from Indiana University. I’ve grown up around animals my entire life, so caring for them has always come naturally to me. While I was in college, I fostered through local animal shelters, which gave me experience caring for animals with all different personalities, ages, and needs. I’m also currently a volunteer at the Anti-Cruelty Society in Chicago, where I help care for animals and support the shelter. I work from home, so I’m able to give pets a lot of attention throughout the day. Your pet will never be left alone for long. My dad is also recently retired and home most of the time, so there’s always someone around to give extra attention, playtime, and care. I have a small Yorkie named Tucker and a cat named Penny. They’re both very friendly and used to being around other animals. Tucker is great at matching other dogs’ energy (whether they want to play or relax), and Penny is very calm and tends to mind her own business. Whether it’s walks, playtime, feeding, or just keeping your pet company, I treat every animal like they’re part of the family. I’d love the opportunity to care for your pet and make sure they feel safe, happy, and comfortable while you’re away! I recently graduated from Indiana University and am now back home in Chicago full-time. My dad is retired and home all day, and I spend most of my time at home too, so your pet will always have company and attention. I’m not super busy and genuinely love being around animals — it’s the perfect setup! I have a private, fully fenced yard and never let pets outside without supervision. My home is spacious, and pets are welcome to relax anywhere they’d like. I also have a 2-year-old, 4.5-pound Yorkie who mostly keeps to himself but is always up for a little playtime if your pet wants a buddy! I’m happy to crate your dog at night if you prefer, or they’re welcome to sleep with me — I’d love that too!

Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$48
per day
5.0 out of 5 stars
207 reviews
51 repeat clients
11 years of experience
Near South Side, Chicago, IL, 60605

Excellent dog care! I booked this because the regular sitter was out of town and was most pleased. Now I know who my next regular sitter would be, should something change with my current one.

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Stavros M.
Sitter Profile Image: Sara T.
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Sara T.
from
$40
per day
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Lower West Side, Chicago, IL, 60608

Thank you so much for taking care of Seymour.

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Anup A.
Sitter Profile Image: Jiayi G.
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Jiayi G.
from
$25
per day
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Jiayi was amazing! Her communication and care exceeded my expectations and she was willing to accept my little one for day care last minute! My pup loved her and she was so good with his potty/feed schedule as well. Definitely booking with her again in the future.

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Japesh P.
Sitter Profile Image: Amy C.
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Amy C.
from
$40
per day
5.0 out of 5 stars
26 reviews
16 repeat clients
15 years of experience
Loop, South Loop, IL, 60605

Amy provided exceptional care for Maeve during her time at daycare. Maeve had an amazing time playing with her new friend Frank, and Amy treated her with the same warmth and attention as if she were her own. I highly recommend Amy and look forward to booking with her again!

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Nelly T.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per day
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

From the moment Teddy entered E. K's home it was like I didn't exist. Kind of like dropping off your kids at preschool and they don't say goodbye. Teddy had a great day with the other dogs especially Allie and will definitely be back.

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Susan L.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$58
per day
5.0 out of 5 stars
102 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni is so amazing!! She watches our puppy when my boyfriend is traveling and I have to be in office and she sends so many updates and our puppy Sally loves seeing her every time.

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Cadence P.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
4.9 out of 5 stars
259 reviews
89 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

I was looking for daycare for my dog and am happy to have found Tamara! She’s great with communication and has been flexible which has been very helpful. And my dogs tail is always wagging when we walk up.

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Jennifer C.
Sitter Profile Image: Ashlee M.
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Ashlee M.
from
$29
per day
5.0 out of 5 stars
1 review
9 years of experience
Near South Side, Chicago, IL, 60616

About: I genuinely treat every dog like my best friend. Full of the upmost love, care, and fun. Your pup isn’t just a pet, they’re family! As a college student with online classes, I love spending my free time with dogs. I have two beautiful huskies of my own back home, so caring for new pups brings me joy every day. I provide personalized care for every pet, whether in my home or yours. I feed, walk, and play with dogs according to their routine, give plenty of love and attention, and make sure they’re safe and comfortable at all times. I also many send updates, photos, and videos so owners know their pets are happy and well cared for.

Sitter Profile Image: Talla A.
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Talla A.
from
$40
per day
4.8 out of 5 stars
27 reviews
11 repeat clients
3 years of experience
Douglas, Chicago, IL, 60616

Excellent communication and clearly responsible. My dog was happy to meet her when I went to leave her a second time. Would strongly recommend.

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Soorya S.
Sitter Profile Image: Trey A.
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Trey A.
Star Sitter
from
$55
per day
5.0 out of 5 stars
63 reviews
24 repeat clients
20 years of experience
Loop, Chicago, IL, 60605

Vi har bokat Trey vid två olika tillfällen och har varit lika nöjd med han båda gångerna. Man får uppdateringar hur det går och mina två hundar tycker om att vara där. Kan varmt rekommendera

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Jesper S.
Sitter Profile Image: Azure D.
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Azure D.
from
$33
per day
15 years of experience
Near South Side, Chicago, IL, 60605

About: I’ve been around animals my entire life, growing up in a home with several dogs and gaining hands-on experience caring for them from a young age. Over the years, I’ve become very comfortable with all aspects of pet care, including administering daily medications and following specific routines to keep pets healthy and stress-free. I’m especially attentive to each animal’s unique needs my own pup, for example, has sensitivities, so I understand how important it is to monitor diet, behavior, and environment closely. In addition to dogs, I also have experience with a variety of animals, as my mom rehabilitated exotic wildlife while I was growing up. That background taught me patience, adaptability, and how to properly care for animals that require extra attention. What sets me apart is how much I prioritize each pet’s health and quality of life. I personally walk my own dog four times a day and bring that same level of care, attention, and routine to every dog I work with. I pride myself on being reliable, detail-oriented, and genuinely loving toward every pet I care for, and I specialize in working with puppies. I work from home, which allows me to be present and attentive to your dog throughout the day. This setup is ideal for pets who need consistent companionship, frequent potty breaks, or a little extra reassurance while you’re away. Whether your dog thrives on attention, has separation anxiety, or simply enjoys having someone nearby, I’m able to provide a calm, supervised environment with plenty of interaction and care. I live in a secure apartment on the third floor with easy ground-level access for quick and convenient potty breaks. My building also offers a dedicated outdoor dog area on the 17th floor, providing a safe and clean space for additional exercise and fresh air. I prioritize safety, routine, and comfort in my home, and I’m happy to follow any specific instructions you have for your pet’s care. To keep you fully at ease, I provide daily, detailed updates with photos so you always know how your dog is doing.

Sitter Profile Image: Jaclyn B.
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Jaclyn B.
from
$35
per day
5.0 out of 5 stars
7 reviews
2 repeat clients
3 years of experience
Loop, Chicago, IL, 60605

Love booking Jaclyn to watch Lincoln. She’s great at providing updates throughout the day!

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Adeline A.
Sitter Profile Image: Jennifer N.
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Jennifer N.
from
$30
per day
4.9 out of 5 stars
265 reviews
124 repeat clients
6 years of experience
Lower West Side, Chicago, IL, 60608

When I first saw Jennifer I knew right away that I could safely leave my dog to her. Cola had a great time with Jen and her family while we had a whole day trip in Chicago city. It’s very convenient that her place is only 15 mins away from the downtown area. Thank you Jen and family -Ryan from Minnesota

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Ryan P.
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Adventure-ready dog walkers - Armour Square

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

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Sitter Profile Image: Angela E.
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Angela E.
Star Sitter
from
$27
per walk
5.0 out of 5 stars
61 reviews
5 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

I have a reactive dog and Angela was very understanding of the situation. I did my best to provide directions, so that and her experience with reactive dogs made it so taking out my dog was a breeze. Definitely will be booking Angela in the future!

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Oscar R.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

About: What sets me aside from other sitters is the love i have for animals. Since i was a little girl I've always loved being around animals they were and still are very therapeutic to me. I've had big dogs from Pitbull's, Dobermann, American bullies, all the way down to tiny dogs; yorkies, shitzu etc. even different kinds of cats you name it. As I've gotten older I've gained sooo much experience to the point I've had at home births with my dogs and cats all by myself; even home training my own animals as well. My goal here is to gain a work related reputation where i can truly start doing what i love and make a name for myself until i can become that super Veterinarian I've always dreamed of being. So far all i have is personal experience with dealing with animals at home and at my job(My residents animals). This would truly mean a lot if i can show off my skills and how genuine i am with animals and even people. Pet Care currently fits for me during the week days. I work doubles every Saturday and Sunday; whereas for school i do online Vet courses which is self pace. Which means i am free during the week Monday-Friday between 9am-5pm if communicated at least at least 30min-1hr in advanced i could stay later if needed. Although, I am a mother which means i can not do any services past 7pm nor any over night services. I also am located downtown Chicago but I am willing to travel!! One thing about me i will spoil your baby(s) haha; I am very hands on and affectionate with animals unless they require space lol. I have never been a crate animal person BUT i know every household is different and every animal requires different training. Again, animals bring a lot of joy to my heart; very therapeutic for me and if given the chance you wouldn't be disappointed i promise!.

Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
39 reviews
7 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine is absolutely wonderful! My dog Maverick tells me about all the fun adventures and colorful sniffs they unfold together. The pictures of Maverick are definitely ones I love to see while I'm off making movie magic to fill his dog bowl and repeat this wonderful cycle. Keep the good vibes going.

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Dominic P.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$18
per walk
5.0 out of 5 stars
31 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

About: While I do not currently share my life with a dog of my own (it's a matter of being unable to adopt every dog I lay my eyes on!), I dearly love helping pet parents keep their dogs happy and healthy and preferably in their own homes while their owners are away. I love to travel,and love to spend time with as many dogs as I can possibly fit into my day. You can often find me chatting with others about their animals, and I am always interested in hearing about every little detail. I enjoy helping people get a greater understanding regarding the welfare of their animals, and sometimes bore my friends with random and obscure dog breeds, and what I know of their temperament and behavior. I'm proud to say I try to research as many breeds as I can so that I know what to expect, and hey, it's always fun to just know why and how a breed came into existence! I happen to also be studying veterinary technology, for the knowledge of nutrition and behavior, since surgery is more information than I want. :D I am also very happy to drop by or stay with your cats, and am quite used to the varying personalities of these small creatures: the ones who like to play hide and seek, the aloof, the playful, and the grumpy. I don't mind at all, as long as the cat is comfortable, eating, and using their litter box, all is well! I can work my day around your dog or cat, as I am a dedicated sitter, and much prefer to spend my time enjoying the company of cats and dogs as much as I can. I much prefer to stay with the dog or cat in their own home, as having their familiar surroundings help them remain peaceful, happy, and comfortable.

Sitter Profile Image: Andres G.
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Andres G.
from
$20
per walk
5.0 out of 5 stars
37 reviews
14 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60608

Andres has been absolutely amazing! He has been amazing to work with. My pittie mix absolutely loves going for his walks with Andres. He is always on time and very professional. Would highly recommend.

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

About: I’ve had my own pets and taken care of others’ pets for decades. I love playing with cats, taking walks with dogs, throwing the ball, and I’m a big-time cuddler. I work from home on my own technology business and I’m available 24 hours a day all over Chicago. I’m also fine with short notice. We have a fantastic gated park across the street that we love taking puppies to. Inside our house there are a dozen different places for dogs and cats to rest. Drop-off and pick-up are easy here, too, as we have a door right onto the street.

Sitter Profile Image: Anastasiia M.
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Anastasiia M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
163 reviews
38 repeat clients
17 years of experience
Near South Side, Chicago, IL, 60616

Anastasiia took great care of Stuart! So thankful to have someone to rely on to help take care of my fur baby. She will for sure be the first on the list whenever I need someone to help with him!

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Leah S.
Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$19
per walk
5.0 out of 5 stars
33 reviews
14 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

Jozelin took Leo on morning walks while I was out of town for a few days. She followed my instructions, was respectful of the space, & was able to handle my Leo. Will book again!! Tyyy

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Cassidy C.
Sitter Profile Image: Mariam A.
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Mariam A.
from
$14
per walk
5.0 out of 5 stars
28 reviews
8 repeat clients
4 years of experience
Bridgeport, Chicago, IL, 60608

Strong communicator and sweet energy with my pets. I was nervous about hiring a dog walker and Mariam helped put me at ease by demonstrating her trustworthiness.

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Heather M.
Sitter Profile Image: Lillian M.
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Lillian M.
from
$25
per walk
5.0 out of 5 stars
28 reviews
9 repeat clients
13 years of experience
Armour Square, Chicago, IL, 60616

Lillian has been great with my dogs and very communicative throughout the walks. She took the time to make sure they were comfortable, shared updates and photos, and went above and beyond with their care. I really appreciated her flexibility and willingness to work with my schedule, especially while I was out of town. I felt confident knowing my dogs were in good hands, and I would absolutely recommend her to other pet parents.

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Carla T.
Sitter Profile Image: Eunice Y.
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Eunice Y.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
67 reviews
28 repeat clients
4 years of experience
Loop, Chicago, IL, 60607

Eunice did a great job communicating AND being independent with taking care of Zoey. She provided a great update and managed to capture Zoey’s full personality in her report card and photos. We will definitely book with Eunice again!

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Jennifer R.
Sitter Profile Image: Nataliia S.
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Nataliia S.
Star Sitter
from
$26
per walk
4.9 out of 5 stars
29 reviews
13 repeat clients
2 years of experience
Near West Side, Chicago, IL, 60608

Natalia was great! She reacted to a last minute request, was very flexible on scheduling when to do the first introduction and most importantly was on time and great with the dogs!

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Brian H.
Sitter Profile Image: Chauntrell W.
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Chauntrell W.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
14 reviews
7 repeat clients
1 year of experience
Bridgeport, Chicago, IL, 60616

I couldn’t be more grateful for the incredible care Chauntrell gave my pup while I was away! From the moment we connected, he was communicative, kind, and clearly passionate about animals. He sent daily updates, photos, and even little notes about how my dog was doing, which gave me so much peace of mind while I was gone. Chauntrell was so patient and gentle with him it didn’t take long before he was completely comfortable and excited for their walks. He treated my pup like he was their own, and that means the world to me. I highly recommend Chauntrell to anyone looking for someone dependable, loving, and professional. I will absolutely be booking with him again in the future! Thank you again for everything my friend! 🐾❤️

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Jordan C.
Sitter Profile Image: Annie X.
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Annie X.
from
$32
per walk
4.9 out of 5 stars
157 reviews
114 repeat clients
8 years of experience
Armour Square, Chicago, IL, 60616

Kaia had a great time with Annie today; brief walk and some cuddle time. She also sent great photos and even brought in our package from the lobby. Thank you! Looking forward to using her services.

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NORMA L.
Sitter Profile Image: Yuuka I.
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Yuuka I.
from
$20
per walk
6 years of experience
Armour Square, Chicago, IL, 60616

About: I’ve been obsessed with dogs my whole life! 🐶 I grew up with my Westie, Rina, and now I’m the proud dog mom of Hiro, who I adopted as a puppy in 2020. I handled all of his potty training, crate training, leash training, and socialization, so I know firsthand that every pup has their own personality and needs. Friends and family have always trusted me to care for their dogs, and I truly treat every pup like they’re my own. Whether your dog loves long walks, playing fetch, or just curling up for cuddles, I’m happy to match their vibe. 😊 Hiro is a sweet, well-socialized little guy who loves making new friends, and I can’t wait to welcome yours into our home. I’ll make sure your pup gets lots of love, attention, exercise, and of course, plenty of photo updates while you’re away! 🐾 I currently work part time and have very flexible availability! My schedule changes every month so my availability is updated regularly. I always make sure to take at least 3 walks per day and get some time and space in to run around to get his energy out! I live nearby several parks that I take hiro to regularly! I also have him crate trained so I can do the same for you and your furbaby as needed :)

Sitter Profile Image: Jenna M.
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Jenna M.
from
$21
per walk
5.0 out of 5 stars
46 reviews
20 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60608

Jenna has been fantastic dog walker for Archer and I! She’s communicative, super responsive, and personable!! Highly recommend her to any pet owner!

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Connor C.
Sitter Profile Image: Jaclyn P.
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Jaclyn P.
from
$20
per walk
14 years of experience
Chicago, IL, 60616

About: As a dog owner for 14 years, I’ve cared for dogs of all ages, including seniors who need extra patience and attention. I genuinely love dogs and will treat your pet with the same care and affection I would my own. I currently work full-time 3 days/week in-person. I’m available to walk or sit on my off days. Just a heads up my availability can vary week to week I prioritize making pets feel safe, comfortable, and cared for while their owners are away. I follow each pet’s routine as closely as possible, including feeding schedules, walks, playtime, medications (if needed), and plenty of attention and affection. In a client’s home, I respect their space and provide regular updates and photos for peace of mind. My goal is to ensure every pet feels loved, secure, and well cared for.

Sitter Profile Image: Nicole R.
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Nicole R.
from
$30
per walk
4.9 out of 5 stars
56 reviews
21 repeat clients
3 years of experience
Bridgeport, Chicago, IL, 60616

Nicole is very responsible, communicates well and is flexible in accommodating requests. Plus my dog loves her.

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James P.
Sitter Profile Image: Matt C.
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Matt C.
from
$25
per walk
5.0 out of 5 stars
125 reviews
21 repeat clients
25 years of experience
Armour Square, Chicago, IL, 60616

Fantastic communication about my puppy! He was so on top of things and even let me know when my dog’s stool looked abnormal (which it was and my puppy was sick).

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Adrienne W.
Sitter Profile Image: Veronica M.
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Veronica M.
from
$35
per walk
5.0 out of 5 stars
7 reviews
2 repeat clients
15 years of experience
Chicago, IL, 60608

Veronica is the best dog Walker. She is flexible and does a very good job making sure my dog gets what he needs while I'm at work. She's a sweet girl who is trusting and cares about what she does. I'm so glad I chose her to care for Rocco.

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Christa R.
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Large dog specialists near you - Armour Square

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

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Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$60
per night
5.0 out of 5 stars
138 reviews
6 repeat clients
1 year of experience
Near South Side, Chicago, IL, 60605

Ania was fantastic and our pup clearly loved spending the weekend with her! She took her to play fetch every day and was flexible with us on our return home. 10/10 would recommend!

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Robert M.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
194 reviews
71 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

Ashley and her daughter treated our dog as if she was their own! Regular updates made me feel so confident that she was well taken care of. No issues with the other dogs she had in her care that weekend either. Will definitely book again!!

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Meg B.
Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
40 reviews
13 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was phenomenal!! 5 out of 5 stars doesn’t even begin to cover it. So easy to communicate with, we received more pictures then we knew what to do with, and she was consistently taking the dogs on walks, to the beach, and out for treats. Couldn’t be more thankful. If we are ever in Chicago again we will be using her services!!

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Tony & Victoria B.
Sitter Profile Image: E K.
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E K.
Star Sitter
from
$45
per night
5.0 out of 5 stars
383 reviews
180 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

I couldn't have asked for a better family to take care of my puppy while I was traveling. I could tell that the family truly enjoyed taking care of my dog Mac and gave him all the love and cuddles he is used to getting. Liz provided numerous pics and updates every day single day. I will definitely re-book the next time I travel! I would highly recommend Liz and family.

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Katie S.
Sitter Profile Image: Bola A.
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Bola A.
from
$45
per night
4.9 out of 5 stars
179 reviews
65 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

We planned our trip ahead of time and Bola made sure to keep open communication along the way. As we dropped our pup off to Bola, the transition was very easy. While Bola had Junie, Bola made sure to keep us updated with pictures. Thanks Bola

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Sean O.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
201 reviews
77 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

Nathan has taken care of our Luna twice now, both times on short notice, and we couldn’t be happier with him. He is incredibly caring, attentive, and truly treats Luna like his own. He kept us feeling completely at ease knowing she was in such good hands. The pickup and drop-off service is an added convenience that we really appreciate. We are so grateful to have found someone we trust and will definitely be using Nathan again in the future. Highly recommend!

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Juhi D.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$40
per night
4.8 out of 5 stars
21 reviews
5 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

Tim is a great guy who is amazing with animals. He provided pictures and updates every day. My dog did not even want to leave. He obviously provided great care and was very flexible with my schedule for pick up and drop off. I really appreciate his dedication and genuine love of animals.

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Daniel G.
Sitter Profile Image: Jenna M.
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Jenna M.
from
$53
per night
5.0 out of 5 stars
96 reviews
22 repeat clients
8 years of experience
Near North Side, Chicago, IL, 60654

Here’s a review you can leave for Jenna on the Rover app: We can't thank Jenna enough for taking such great care of our dog, Lola, while we were away for a family funeral. She went above and beyond, sending us daily pictures and updates that gave us peace of mind during a difficult time. When we missed our flight and needed to extend Lola's stay, Jenna was incredibly accommodating and flexible, which was a huge relief. Lola clearly loved her, and we could tell she was in the best hands. Jenna is sweet, reliable, and a true dog lover. I highly recommend her to anyone looking for a trustworthy and caring dog sitter! We will definitely be using her services again!

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Devina C.
Sitter Profile Image: Jiayi G.
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Jiayi G.
from
$40
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

Jiayi was awesome and I really appreciated all the pics and videos she sent! Perfect person for my firework anxious dog to spend the 4th with. Thank you so much Jiayi!

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Kristine P.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
363 reviews
99 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

Katie is so amazing!! So flexible with timing, kind, and sends pictures! She also was so nice in meeting me before so I could make sure my dog would be okay with her dog. Her dog is so chill so it was perfect for my anxious dog. Thank you so much again Katie!!! Definitely will book again 😊😊😊

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Ana H.
Sitter Profile Image: Sarah B.
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Sarah B.
Star Sitter
from
$50
per night
4.9 out of 5 stars
53 reviews
10 repeat clients
21 years of experience
Bridgeport, Chicago, IL, 60616

Sarah B was so nice and accommodating. This is the first time my pet has stayed with a sitter and my mind was completely at ease. Thanks Sarah!

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Anne S.
Sitter Profile Image: Christina L.
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Christina L.
from
$55
per night
5.0 out of 5 stars
63 reviews
21 repeat clients
15 years of experience
West Town, Chicago, IL, 60622

Amazing sitter for our dog! This was our first time leaving her for so many days not with family. Christina was great about sending updates and took wonderful care of Gobi. Will absolutely book with her again!!

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Pranshul G.
Sitter Profile Image: Angel V.
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Angel V.
Star Sitter
from
$47
per night
5.0 out of 5 stars
111 reviews
30 repeat clients
15 years of experience
Humboldt Park, Chicago, IL, 60624

He went above and beyond what I expected. The retractable leash broke so he bought another 1. He didn't have to do that but he did. Always sent me photos daily. Highly would recommend Angel.

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Matt L.
Sitter Profile Image: Steven R.
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Steven R.
Star Sitter
from
$58
per night
5.0 out of 5 stars
49 reviews
20 repeat clients
50 years of experience
Near North Side, Chicago, IL, 60611

Steven was great! He has a calm disposition and Jessy loved him. He took her on a walk and played fetch and kept me updated with photos! Would definitely use him again.

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Rachel A.
Sitter Profile Image: Iwona K.
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Iwona K.
from
$50
per night
5.0 out of 5 stars
610 reviews
202 repeat clients
22 years of experience
West Town, Chicago, IL, 60622

We were a bit nervous leaving our Louie for the first time in years. Iwona’s attention and love to him was evident as he came back happy from his own vacation! The daily pictures and updates were very helpful. We will definitely use Iwona again and again. Thank you!

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Katherine H.
Sitter Profile Image: Fred C.
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Fred C.
Star Sitter
from
$50
per night
4.9 out of 5 stars
39 reviews
8 repeat clients
25 years of experience
Lower West Side, Chicago, IL, 60616

Fred was absolutely wonderful to coordinate with, super responsive! And he sent daily updates and pics of our sweet boy. Dante was the right amount of excited to see us, and I think he definitely enjoyed his time with Fred. Thank you so much!!!!

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Antonia H.
Sitter Profile Image: Samantha M.
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Samantha M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
28 reviews
7 repeat clients
10 years of experience
West Town, Chicago, IL, 60642

Sam took great care of my boy Kimi when I was out of town. I appreciated the daily updates, pictures and videos! She made sure Kimi stayed warm when snow storm hit and made Kimi felt like being at home. Would definitely choose Sam again if I need a sitter in the future!

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Guanjin C.
Sitter Profile Image: Fortino V.
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Fortino V.
Star Sitter
from
$41
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
5 years of experience
West Town, Chicago, IL, 60642

Fortino was amazing! My dog is pretty high energy and I could tell he was having a great time. Fortino sent regular updates and he took my dog on lots of fun excursions with his own dog. He was very communicative and I could tell he paid close attention to details of my dog’s comfort, personality, etc. He even gave my dog a sweater that previously belonged to his dog but was too small, which was very sweet. Will definitely board with him again.

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Andrea S.
Sitter Profile Image: Craila N.
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Craila N.
from
$55
per night
5.0 out of 5 stars
22 reviews
6 repeat clients
20 years of experience
Near West Side, Chicago, IL, 60608

Craila was amazing with Ziggy! He is super high energy and can be a lot of handle. She was great with him and tires him out. She sent us lots of updates! We will absolutely be using Craila for Ziggy in the future!

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Heather M.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$65
per night
5.0 out of 5 stars
102 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni took great care of my buddy! She sent regular updates and pictures. I knew he was in great hands which made it much easier to be away. Bunk looks forward to his next visit!

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Rebecca R.
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