Doggy Day Care in Grand Boulevard, Chicago

Drop off your dog at a sitter’s home or day care center in the morning and pick them up in the evening.

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Top rated Grand Boulevard doggy day care sitters

1 / 1
Sitter Profile Image: Bola A.
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Bola A.
Star Sitter
from
$42
per day
5 out of 4.9 stars
121 reviews
34 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Bola came through for me last minute and took great care of Bea!! She sent me picture updates and communicated well throughout the day. Will definitely be booking again with her.

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Abby B.
Sitter Profile Image: E K.
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E K.
from
$45
per day
5 out of 5.0 stars
320 reviews
146 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

Elizabeth was a pleasure to deal with from first contact until we picked Tika up at the end of the night. Amazing communication and pictures.

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David B.
Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Star Sitter
from
$40
per day
5 out of 5.0 stars
65 reviews
20 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60605

Katrina was excellent! She made my first Rover experience with my pup a breeze. She is incredibly responsive and is punctual. She walked me through everything to expect and she even helped me set up a day stay as a introduction for my pup before her longer 5 night stay. I felt that my dog was well cared for and was receiving so much attention and love from Katrina! I got many updates and cute photos through the day which made me feel at ease while at work. She even gave me a little souvenir photo of my pup at the end of the stay. She is also very professional and transparent about every aspect of the stay. I give her my highest recommendation and will definitely be a repeat client!

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Mamtha R.
Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter
from
$45
per day
5 out of 5.0 stars
112 reviews
51 repeat clients
23 years of experience
Hyde Park, Chicago, IL, 60615

Ashley was great with Kash! She loved him and he loved her! She constantly sent updates and photos of my little guy having fun. Your pup is in good hands in Ashley’s care!

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Amber B.
Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter
from
$45
per day
5 out of 5.0 stars
79 reviews
5 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: Czarina H.
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Czarina H.
from
$48
per day
5 out of 5.0 stars
7 reviews
2 repeat clients
15 years of experience
Near West Side, Chicago, IL, 60608

About: I grew up with family dogs and have had mine since he was 8 weeks old (he will be 16 years old this August!). Experience with puppies through senior dogs. Large breeds and small! Would love to take care of yours. I work full time from home, so I have ample amount of time to hang out with your pups (no matter the age, dogs are forever pups in my eyes!). I have an almost 16 year old pup who naps most of the day but is always excited for his walks! I live in a low traffic area and just down the street from a fenced grass area we play in. In case there’s rain, I have a covered area to take the pups out so they still get some fresh air.

Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$40
per day
5 out of 5.0 stars
116 reviews
39 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: David R.
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David R.
Star Sitter
from
$62
per day
5 out of 5.0 stars
335 reviews
83 repeat clients
10 years of experience
Loop, Chicago, IL, 60605

David took excellent care of our dog, Maaya, during the work day. Response from David was quick, drop off/pick up and communication with David was easy, and he sent regular updates through out the day. He also made sure to ask about food, treats, etc and kept me up to date on her breaks after the stay. Maaya is excited to return for future play dates with David and his dogs! Would highly recommend!

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Dana Z.
Sitter Profile Image: Lisette S.
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Lisette S.
Star Sitter
from
$27
per day
5 out of 5.0 stars
54 reviews
9 repeat clients
8 years of experience
McKinley Park, Chicago, IL, 60609

About: I've been taking care of pets since the I was 12. My family and I have had one english bulldog. Currently we have two french bulldogs, so I understand the importance of the care of bulldogs as well as Chihuahuas! I have always been the go to person to care for and groom our pets. I'm currently in college full time. However, it is online so I have a lot of time to play, walk, and give love to your pets! I have a fenced yard as well as two dogs to play with your pets. I also have one cat. I live close to the Mckinley Park area so there will be a lot of walks.

Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$40
per day
5 out of 5.0 stars
132 reviews
46 repeat clients
15 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: Daphnay S.
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Daphnay S.
Star Sitter
from
$45
per day
5 out of 5.0 stars
13 reviews
5 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

About: Looking for a dog sitter with a passion for pups and years of experience? I’ve not only been a dog mom for 14 years, but recently assisting in training the now 6 month old puppy that’s in my parent’s care. I’m the #1 dog sitter amongst my network, not only because I work from home and have availability, but because I also include their fur babies in my dog’s activities as well i.e. dog park dates, dog birthday parties, and doggie brunch! I’m a full- time remote employee with a very relaxed work schedule. Your pet will be spending the majority of their time in my care. I have a fenced front yard and a patio along with one 22lbs dog that will keep your pet company. I also have a lot of space to allow the dog to move around as they would like.

Sitter Profile Image: Xinwen M.
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Xinwen M.
Star Sitter
from
$44
per day
5 out of 5.0 stars
33 reviews
8 repeat clients
3 years of experience
Armour Square, Chicago, IL, 60616

About: Hi! This is Xinwen. I’ve been living with pets since I was a kid. I’m currently a volunteer at Anti-Cruelty shelter to help both dogs and cats, and I’m proud of it. I WFH and have plenty of time to take your pets out/ play at home. I’m very familiar with pets’ behaviors and could tell what they want: attentions, some alone time, an exciting hunting game…., by their body language. I keep track of their eating patterns and defecation performance, as those are important and straight forward reflections of their moods and health conditions. By these experiences I could give them more accurate cares. Also, I guarantee that I report the real conditions of your babies, instead of pretending they’re doing great just to win your approval. I respect them as human beings. :) I love both dogs and cats. I enjoy spending time with them. Also, I’m very patient and careful. I’ll make sure that your pet(s) get what they need and feel loved! I’m free to arrange drop-ins or walks every workday 7:00-8:00pm. I’m available for boarding and day care every day. Other flexible hours can be discussed with me too! I’m available for drop-ins and overnight stay in your home. I always make sure to provide them fresh food and water, clean the litter box and play/walk with them.

Sitter Profile Image: Pamela K.
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Pamela K.
from
$40
per day
5 out of 4.8 stars
31 reviews
12 repeat clients
20 years of experience
Grand Boulevard, Chicago, IL, 60615

Pamela is the sweetest and Charlie simply LOVES her. I'm so grateful that she cares for him so lovingly and truly enjoys him. She sends sweet updates that warm my heart. Why leave him alone when he can be so well cared for! I'll book with her again and again!!

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Karen N.
Sitter Profile Image: Keianna M.
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Keianna M.
from
$35
per day
5 out of 5.0 stars
2 reviews
7 years of experience
Woodlawn, Chicago, IL, 60637

About: I bring hands-on experience and genuine love for animals into every pet-sitting job. I have two dogs of my own (ages 7 and 4) whom I trained myself from puppyhood—including potty training by 6 months! I groom them myself regularly, take them on daily walks, and have experience administering medications for allergies, ear infections, preventative care, and post-procedure care. Whether your pet needs structured training support, gentle senior care, or just someone who truly understands their needs and routines, I'm here to offer reliable, compassionate service. Your pets will be treated like family—because that’s exactly how I treat my own. As a medical student who primarily studies from home, I have a very flexible and consistent schedule. Outside of 2-3 hours a day when I’m on campus, I’m home and fully available to care for pets. This allows me to give them plenty of attention, regular walks, playtime, and any needed care throughout the day. Having a structured but home-based routine makes it easy for me to prioritize your pet’s needs and keep them happy, healthy, and comfortable while you're away. Whether I’m caring for pets in my home or in a client’s, my approach is all about providing a safe, loving, and low-stress environment that mirrors their usual routine as closely as possible. In my home, pets have a calm, pet-friendly space where they can relax, play, and enjoy plenty of attention. I do daily walks, structured feeding times, and lots of one-on-one interaction. If I’m caring for pets in their own home, I make it a priority to maintain their normal schedule—walks, meals, playtime, and any special instructions—so they feel secure and comfortable in their familiar surroundings. I’m also experienced with medication administration and basic grooming, and I keep pet parents updated regularly with messages and photos so they can feel at ease while they’re away.

Sitter Profile Image: Madeleine F.
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Madeleine F.
from
$55
per day
5 out of 5.0 stars
30 reviews
6 repeat clients
7 years of experience
Kenwood, Chicago, IL, 60615

Madeleine was so kind and accommodating. She was very easy to communicate with and was always prompt in her communications. She sent us multiple pictures as well. Highly recommend.

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Carrie S.
Sitter Profile Image: Willy J.
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Willy J.
from
$35
per day
5 out of 5.0 stars
22 reviews
8 repeat clients
10 years of experience
Douglas, Chicago, IL, 60653

Willy was amazing with my pup! I love that he has the skill to assist me with my 11wk pup with potty training. Very attentive with my baby and a lot of play time! Love the consistency with the updates and pictures and videos though out the day! Definitely will book against ten stars ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

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Dominique O.
Sitter Profile Image: Tiffany O.
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Tiffany O.
from
$50
per day
5 out of 5.0 stars
6 reviews
2 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60615

About: With over two decades of dedicated experience in pet care, I have nurtured and cherished dogs of all ages, from playful puppies to wise elderly companions. My profound joy in this journey stems from the deep connections formed with these furry friends. Having worked with a diverse array of breeds, I've honed my understanding of their unique needs and temperaments. In addition, my expertise extends to puppy training, where patience and consistency are key. Caring for dogs isn't just a passion; it's a lifelong commitment that brings immense fulfillment. I work a full time remote schedule. I am at home Mondays and Fridays. Im off on the weekends. So I have plenty of time to play and go on walks! I have a small yorkie that can keep your baby company and I have a baby gate for safe separation if needed. I can also crate your baby if that is what you prefer. Your pets can sleep in the room with me on there beds or wherever makes them most comfortable

Sitter Profile Image: Joseph G.
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Joseph G.
from
$60
per day
5 out of 5.0 stars
5 reviews
2 repeat clients
15 years of experience
Oakland, Chicago, IL, 60653

About: I have a beautiful, clean home with a beautiful dog run. I am trustworthy and have references for your approval. I come from the pet industry and work from home. I work from home and teach online cooking classes. I have a very flexible schedule to accommodate any needs. I am available 7 days a week, including holidays. I have dog training experience and will care for your dog as if it were my own. I have a pet profile I will ask you to complete so that I can provide the best care possible.

Sitter Profile Image: Jabari R.
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Jabari R.
from
$33
per day
5 out of 4.6 stars
9 reviews
3 repeat clients
4 years of experience
Grand Boulevard, Chicago, IL, 60621

About: I have had dogs and cats my whole life,my entire family loves animals I am very flexible because I know everyone cares for their pets differently I totally fine with any special cases under humane circumstances.Am doing this as a work at will job because after working for the aspca I have learned that pets are a essential part to anyone’s life.I also work as delivery biker so this job fits into my schedule, my hope is that before the end of the summer I have my high school diploma paid off Nd u have earned enough to purchase a car with no lease. I have high hopes for myself and I thank you for reading my bio and look forward to working with your lovely pets. Am a independent contractor so I work from home 10-20 hours a work am able to watch dogs at the same time I have treats and doggy tv. I have a fenced in yard and one fur baby to keep your dog company and I have a extra large crate if needed my little girl daisy is a small dog she on only likes to play with small dogs

Sitter Profile Image: Taylor C.
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Taylor C.
from
$30
per day
5 out of 4.8 stars
26 reviews
10 repeat clients
7 years of experience
Hyde Park, Chicago, IL, 60615

Mable was treated so well and I would highly recommend Taylor. My dog is usually very anxious when I leave her but I felt very confident about her stay with Taylor!!! I will definitely be using her services again!!! Thank you!!!

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Paula L.
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Sitter Profile Image: Bola A.
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Sitter Profile Image: Bola A.
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Bola A.
Star Sitter

Big time dog lover 😄
Hyde Park, Chicago, IL, 60615
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$42
per day
5 out of 4.9 stars
121 reviews
34 repeat clients
Profile image

Bola came through for me last minute and took great care of Bea!! She sent me picture updates and communicated well throughout the day. Will definitely be booking again with her.

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: E K.
Verified Background Check
Sitter Profile Image: E K.
Verified Background Check

E K.
Rover 101

Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
320 reviews
146 repeat clients
Profile image

Elizabeth was a pleasure to deal with from first contact until we picked Tika up at the end of the night. Amazing communication and pictures.

Availability updated 6 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Hua “Katrina” F.
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Sitter Profile Image: Hua “Katrina” F.
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Hua “Katrina” F.
Rover 101
Star Sitter

🏠Wedding Planner + Dog Mom
Near South Side, Chicago, IL, 60605
3.7 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
65 reviews
20 repeat clients
Profile image

Katrina was excellent! She made my first Rover experience with my pup a breeze. She is incredibly responsive and is punctual. She walked me through everything to expect and she even helped me set up a day stay as a introduction for my pup before her longer 5 night stay. I felt that my dog was well cared for and was receiving so much attention and love from Katrina! I got many updates and cute photos through the day which made me feel at ease while at work. She even gave me a little souvenir photo of my pup at the end of the stay. She is also very professional and transparent about every aspect of the stay. I give her my highest recommendation and will definitely be a repeat client!

Availability updated today
Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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Ashley B.
Star Sitter

Open house for Pets
Hyde Park, Chicago, IL, 60615
2.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
112 reviews
51 repeat clients
Profile image

Ashley was great with Kash! She loved him and he loved her! She constantly sent updates and photos of my little guy having fun. Your pup is in good hands in Ashley’s care!

Availability updated 8 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Ania Z.
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Sitter Profile Image: Ania Z.
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Ania Z.
Star Sitter

WFH, pet loving, parks nearby
Near South Side, Chicago, IL, 60605
3.6 mi. away
Boarding, Doggy Day Care
from
$45
per day
5 out of 5.0 stars
79 reviews
5 repeat clients
Profile image

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.

Availability updated 8 days ago
Sitter Profile Image: Czarina H.
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Sitter Profile Image: Czarina H.
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Czarina H.

Take a break - I got your pup!
Near West Side, Chicago, IL, 60608
4.0 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$48
per day
5 out of 5.0 stars
7 reviews
2 repeat clients

About: I grew up with family dogs and have had mine since he was 8 weeks old (he will be 16 years old this August!). Experience with puppies through senior dogs. Large breeds and small! Would love to take care of yours. I work full time from home, so I have ample amount of time to hang out with your pups (no matter the age, dogs are forever pups in my eyes!). I have an almost 16 year old pup who naps most of the day but is always excited for his walks! I live in a low traffic area and just down the street from a fenced grass area we play in. In case there’s rain, I have a covered area to take the pups out so they still get some fresh air.

Availability updated 7 days ago
Sitter Profile Image: Ashley M.
Verified Enhanced Background Check
Sitter Profile Image: Ashley M.
Verified Enhanced Background Check

Ashley M.
Rover 101
Star Sitter

WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$40
per day
5 out of 5.0 stars
116 reviews
39 repeat clients
Profile image

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! :)

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: David R.
Verified Enhanced Background Check
Sitter Profile Image: David R.
Verified Enhanced Background Check

David R.
Rover 101
Star Sitter

Stay at Home Lawyer + Dog Dad
Loop, Chicago, IL, 60605
3.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$62
per day
5 out of 5.0 stars
335 reviews
83 repeat clients
Profile image

David took excellent care of our dog, Maaya, during the work day. Response from David was quick, drop off/pick up and communication with David was easy, and he sent regular updates through out the day. He also made sure to ask about food, treats, etc and kept me up to date on her breaks after the stay. Maaya is excited to return for future play dates with David and his dogs! Would highly recommend!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Lisette S.
Verified Enhanced Background Check
Sitter Profile Image: Lisette S.
Verified Enhanced Background Check

Lisette S.
Star Sitter

For the love of pets!
McKinley Park, Chicago, IL, 60609
3.0 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$27
per day
5 out of 5.0 stars
54 reviews
9 repeat clients

I hired Lisette to walk and care for my 6 year old golden retriever/pit bull mix rescue dog Lucy whenever I would go out of town for business. Lisette is the daughter of my co-worker, the first time she met my best friend Lucy, Lucy was a bit standoffish due to her being uneasy around strangers. After a few hours Lucy loved Lisette and felt comfortable around her. Lisette would care for Lucy for 2 weeks every month while I was away, she would send me daily pictures of their walks or when they were just hanging out. Sometimes Lucy wouldn't want to leave Lisette's apartment. Although I don't travel as much I still employ Lisette to walk Lucy just so that Lucy can see her good friend Lisette. I definitely recommend Lisette to care for your 4 legged friends. Lisette would also watch over my 3 year old cat Benito. Although Benito does not need much maintenance Lisette always makes time to play with him and ensures he eats his food. Lisette also recommended for me to add water to his wet food to ensure he drinks more water for health reasons. I cannot recommend Lisette enough, she is good at what she does, I have also recommended her to other friends who do not have time to walk tbeir 4 legged friends.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tamara J.
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Sitter Profile Image: Tamara J.
Verified Enhanced Background Check

Tamara J.
Star Sitter

Experienced Dog Owner
Grand Boulevard, Chicago, IL, 60653
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
132 reviews
46 repeat clients
Profile image

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.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Daphnay S.
Verified Enhanced Background Check
Sitter Profile Image: Daphnay S.
Verified Enhanced Background Check

Daphnay S.
Star Sitter

Dog Lover and Owner
Douglas, Chicago, IL, 60653
1.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$45
per day
5 out of 5.0 stars
13 reviews
5 repeat clients

Daphnay is always my first choice when looking for a sitter for my dog! My dog gets so excited when we get to her door. I can always trust that my dog is safe, comfortable, and having a good time with her. I absolutely recommend Daphnay!

Availability updated 11 days ago
Sitter Profile Image: Xinwen M.
Verified Enhanced Background Check
Sitter Profile Image: Xinwen M.
Verified Enhanced Background Check

Xinwen M.
Star Sitter

A 200% genuine petlover!
Armour Square, Chicago, IL, 60616
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$44
per day
5 out of 5.0 stars
33 reviews
8 repeat clients

About: Hi! This is Xinwen. I’ve been living with pets since I was a kid. I’m currently a volunteer at Anti-Cruelty shelter to help both dogs and cats, and I’m proud of it. I WFH and have plenty of time to take your pets out/ play at home. I’m very familiar with pets’ behaviors and could tell what they want: attentions, some alone time, an exciting hunting game…., by their body language. I keep track of their eating patterns and defecation performance, as those are important and straight forward reflections of their moods and health conditions. By these experiences I could give them more accurate cares. Also, I guarantee that I report the real conditions of your babies, instead of pretending they’re doing great just to win your approval. I respect them as human beings. :) I love both dogs and cats. I enjoy spending time with them. Also, I’m very patient and careful. I’ll make sure that your pet(s) get what they need and feel loved! I’m free to arrange drop-ins or walks every workday 7:00-8:00pm. I’m available for boarding and day care every day. Other flexible hours can be discussed with me too! I’m available for drop-ins and overnight stay in your home. I always make sure to provide them fresh food and water, clean the litter box and play/walk with them.

Availability updated 31 days ago
Sitter Profile Image: Pamela K.
Verified Background Check
Sitter Profile Image: Pamela K.
Verified Background Check

Pamela K.

Dogs are four legged best friends
Grand Boulevard, Chicago, IL, 60615
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 4.8 stars
31 reviews
12 repeat clients
Profile image

Pamela is the sweetest and Charlie simply LOVES her. I'm so grateful that she cares for him so lovingly and truly enjoys him. She sends sweet updates that warm my heart. Why leave him alone when he can be so well cared for! I'll book with her again and again!!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Keianna M.
Verified Enhanced Background Check
Sitter Profile Image: Keianna M.
Verified Enhanced Background Check

Keianna M.

Loving Care When You Can’t Be There
Woodlawn, Chicago, IL, 60637
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
2 reviews

About: I bring hands-on experience and genuine love for animals into every pet-sitting job. I have two dogs of my own (ages 7 and 4) whom I trained myself from puppyhood—including potty training by 6 months! I groom them myself regularly, take them on daily walks, and have experience administering medications for allergies, ear infections, preventative care, and post-procedure care. Whether your pet needs structured training support, gentle senior care, or just someone who truly understands their needs and routines, I'm here to offer reliable, compassionate service. Your pets will be treated like family—because that’s exactly how I treat my own. As a medical student who primarily studies from home, I have a very flexible and consistent schedule. Outside of 2-3 hours a day when I’m on campus, I’m home and fully available to care for pets. This allows me to give them plenty of attention, regular walks, playtime, and any needed care throughout the day. Having a structured but home-based routine makes it easy for me to prioritize your pet’s needs and keep them happy, healthy, and comfortable while you're away. Whether I’m caring for pets in my home or in a client’s, my approach is all about providing a safe, loving, and low-stress environment that mirrors their usual routine as closely as possible. In my home, pets have a calm, pet-friendly space where they can relax, play, and enjoy plenty of attention. I do daily walks, structured feeding times, and lots of one-on-one interaction. If I’m caring for pets in their own home, I make it a priority to maintain their normal schedule—walks, meals, playtime, and any special instructions—so they feel secure and comfortable in their familiar surroundings. I’m also experienced with medication administration and basic grooming, and I keep pet parents updated regularly with messages and photos so they can feel at ease while they’re away.

Availability updated 13 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Madeleine F.
Verified Background Check
Sitter Profile Image: Madeleine F.
Verified Background Check

Madeleine F.

I'll love ur dog while you're away!
Kenwood, Chicago, IL, 60615
1.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per day
5 out of 5.0 stars
30 reviews
6 repeat clients
Profile image

Madeleine was so kind and accommodating. She was very easy to communicate with and was always prompt in her communications. She sent us multiple pictures as well. Highly recommend.

Availability updated 34 days ago
Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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Willy J.

Reliable Dog Lover at your Service
Douglas, Chicago, IL, 60653
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
22 reviews
8 repeat clients
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Willy was amazing with my pup! I love that he has the skill to assist me with my 11wk pup with potty training. Very attentive with my baby and a lot of play time! Love the consistency with the updates and pictures and videos though out the day! Definitely will book against ten stars ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Tiffany O.
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Sitter Profile Image: Tiffany O.
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Tiffany O.

WFH dog mom, I'd ❤️ to host you pet
Hyde Park, Chicago, IL, 60615
1.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$50
per day
5 out of 5.0 stars
6 reviews
2 repeat clients

About: With over two decades of dedicated experience in pet care, I have nurtured and cherished dogs of all ages, from playful puppies to wise elderly companions. My profound joy in this journey stems from the deep connections formed with these furry friends. Having worked with a diverse array of breeds, I've honed my understanding of their unique needs and temperaments. In addition, my expertise extends to puppy training, where patience and consistency are key. Caring for dogs isn't just a passion; it's a lifelong commitment that brings immense fulfillment. I work a full time remote schedule. I am at home Mondays and Fridays. Im off on the weekends. So I have plenty of time to play and go on walks! I have a small yorkie that can keep your baby company and I have a baby gate for safe separation if needed. I can also crate your baby if that is what you prefer. Your pets can sleep in the room with me on there beds or wherever makes them most comfortable

Availability updated 11 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Joseph G.
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Sitter Profile Image: Joseph G.
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Joseph G.

Professional Pet Care by a Pro
Oakland, Chicago, IL, 60653
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per day
5 out of 5.0 stars
5 reviews
2 repeat clients

Joseph has been an incredible asset to me. We needed help and needed it fast. We were clueless about how to care for our new dog from Lollypop Farms. Joseph came to my house, met the dog and immediately became part of our family. I love Joseph and all he does for my furry family.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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Jabari R.

Former face to face fundraiser
Grand Boulevard, Chicago, IL, 60621
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$33
per day
5 out of 4.6 stars
9 reviews
3 repeat clients

Jabari is currently a co-owner of a 8-12 month old Yorkshire Terrier mix currently alongside me whom he frequently feeds, grooms and bonds with on a daily basis. Jabari has experience with both large and small breeds of dogs, he has worked with 1+ year old male Pure breed Cane Corso and 1+ year old female German Shepherd Mix who he has cared for and watched over several times over their life. As well as, already pet-sitting a variety of dogs for many owners within his own family. I would highly recommend Jabari for care for other's pets as he is responsible, caring and diligent about the well-being of all pets and properly caring for them according to their breeds, sizes and ages.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 4.8 stars
26 reviews
10 repeat clients
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Mable was treated so well and I would highly recommend Taylor. My dog is usually very anxious when I leave her but I felt very confident about her stay with Taylor!!! I will definitely be using her services again!!! Thank you!!!

Availability updated 10 days ago

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