Personalized care for your dog or cat - Winnetka

Highly-rated overnight sitters - Winnetka

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

1 / 1
Sitter Profile Image: Rizwan & Noorjahan M.
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Rizwan & Noorjahan M.
Star Sitter
from
$30
per night
5.0 out of 5 stars
42 reviews
10 repeat clients
6 years of experience
Morton Grove, IL, 60053

Rizwan, Noorjahan and their family were such great sitters for our dog and cat! They are such a sweet family and we received many pictures every day. I was reassured that both my pets were having a great time with them! Will definitely reach out again for our next sitting.

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Marianne W.
Sitter Profile Image: Naomi & Johann J.
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Naomi & Johann J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
15 years of experience
Glenview, IL, 60025

Naomi was great!! She was very prepared and ready to learn about and to care for our dogs just the way they needed. Our dogs had the best time taking long walks, lounging, and looking out the big window. She took the time to introduce our dogs and Milo and they became great friends. The house was quiet, very clean, and perfect for our dogs. We loved seeing the daily photos while we were traveling. Definitely would recommend!

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Ashley Kate J.
Sitter Profile Image: Thao T.
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Thao T.
from
$45
per night
4.9 out of 5 stars
102 reviews
56 repeat clients
12 years of experience
Wilmette, IL, 60091

Thao was absolutely the right choice for us and Ginny! We have now found the person we will always use in the future. Thao is loving and caring with all the dogs she watches!

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Jim M.
Sitter Profile Image: Rima B.
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Rima B.
Star Sitter
from
$39
per night
5.0 out of 5 stars
130 reviews
56 repeat clients
13 years of experience
SKOKIE, IL, 60077

Rima is so kind and patient. We received photos of our pups daily and they seemed to have a small adjustment but in the end they seemed like they enjoyed themselves. Rima is flexible and she made the process smooth and effortless. Thank you, Rima!

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Grace L.
Sitter Profile Image: Lauren G.
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Lauren G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
22 reviews
7 repeat clients
20 years of experience
Niles, IL, 60714

Lauren, and her family, were so kind, communicative and caring for our old boy! We couldn’t have been happier with Aspen’s care and are so grateful he was in such great hands!

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Kileen C.
Sitter Profile Image: Merrick R.
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Merrick R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
48 reviews
8 repeat clients
5 years of experience
Skokie, IL, 60076

Merrick took care of our dog for a long weekend. Communication was good and easy, and our dog came home afterwards very happy and settled. Very happy with this experience, and we will use Merrick again in the future.

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Reuben K.
Sitter Profile Image: Claire C.
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Claire C.
Star Sitter
from
$42
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
30 years of experience
Morton Grove, IL, 60053

Claire was wonderful with Hazel (older dog) and Sam (older cat). This was the first time we used a pet care service and we were very fortunate to find Claire. She is thoughtful, kind, skilled with dogs and cats, and an excellent communicator. Hazel can be reactive to other dogs on walks; Claire was familiar with the ractive dogs and managed it with well. She also messaged us once a day while we were away with details and pictures. We have already booked with Claire again.

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Christine D.
Sitter Profile Image: Doug & Deb B.
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Doug & Deb B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
81 reviews
15 repeat clients
44 years of experience
Jefferson Park, Chicago, IL, 60646

Doug & Deb are wonderful pet parents! With short notice, they took in my senior dog and made her feel home. Well cared for and exercised. We will definitely come back!

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Gudrun P.
Sitter Profile Image: Hannah F.
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Hannah F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
116 reviews
43 repeat clients
9 years of experience
Wheeling, IL, 60090

Hannah was amazing with our 9‑month‑old puppy, Romeo! She took such good care of him, made sure he was fed on time, and went out of her way to keep him comfortable and happy while we were gone. She kept sending us the cutest pics and videos, which really helped us relax on our trip. Romeo clearly had the best time with her, and we’ll definitely be booking her again every time we need boarding for Romeo. Highly recommend her to any friends looking for a super sweet and reliable pet sitter!

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Sawan K.
Sitter Profile Image: Ella V.
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Ella V.
Star Sitter
from
$90
per night
5.0 out of 5 stars
281 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

We were thrilled with Rosie's stay with Ella. From the moment we arrived and Ella showed us around, Rosie felt so comfortable. She was welcomed to explore the apartment and snuggle into the sofa. Ella sent several updates with photos and we felt very confident Rosie was being well cared for - with much time for play and walks. We will definitely book with Ella again.

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Deborah L.
Sitter Profile Image: Kimberly R.
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Kimberly R.
Star Sitter
from
$45
per night
4.9 out of 5 stars
89 reviews
26 repeat clients
9 years of experience
Norwood Park, Chicago, IL, 60646

We had such a wonderful experience, this was our second time leaving Korra with Kim, and once again she was amazing. She took excellent care of Korra, and her communication was great, which gave us complete peace of mind. Kim truly went above and beyond; she even got Korra a Christmas gift, which meant so much to us. We’re incredibly grateful and would absolutely book with her again. Highly recommend!

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Jessica J.
Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

Great experience overall. Rebeca was communicative, reliable, and took good care of my dogs. I felt comfortable while I was away and would happily book again.

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Robert G.
Sitter Profile Image: Meghan M.
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Meghan M.
from
$50
per night
5.0 out of 5 stars
1 review
15 years of experience
Northbrook, IL, 60062

Five very waggy stars for Meghan (and her sweet pup, Ralphie)! Meghan is absolutely incredible. From the moment we arrived, it was clear that she is a true dog lover with tons of experience, and she knew exactly how to make our dog feel safe, happy, and completely at home. Our dog was treated like a member of her family and had the time of his life playing with Ralphie and the other dogs. The adorable photos and videos gave us so much peace of mind while we were away...and honestly, I think he was a little sad to come home, which is probably the highest compliment a dog can give. We will absolutely book again. Weekend at Ralphie’s is officially dog-approved!

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Colleen C.
Sitter Profile Image: Jeffrey & Ron R.
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Jeffrey & Ron R.
from
$60
per night
5.0 out of 5 stars
41 reviews
14 repeat clients
49 years of experience
Evanston, IL, 60202

This was our first time our 6 year old dog, Kona, stayed over at another dog sitter's home. Our dog is anxious and slow to warm up to people. Jeff and Ron were very warm, welcoming, and patient with Kona. We received regular updates and pictures. Our dog was in good spirits when we picked him up. We will definitely contact Jeff and Ron in the future!

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Michaela C.
Sitter Profile Image: Cynthia A.
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Cynthia A.
Star Sitter
from
$65
per night
5.0 out of 5 stars
71 reviews
24 repeat clients
25 years of experience
EVANSTON, IL, 60202

Cynthia treats my dog like he’s her own, he always has a great time and I feel stress free knowing he’s with her! The best pup sitter around!

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Cole K.
Sitter Profile Image: Kazuhiro & Akemi S.
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Kazuhiro & Akemi S.
Star Sitter
from
$85
per night
5.0 out of 5 stars
203 reviews
54 repeat clients
35 years of experience
Wilmette, IL, 60091

Kazuhiro and Akemi were simply fantastic with Regina George! She is a bit timid but was very comfortable with them and their other sweet dog guests. You could see how calm and relaxed all dogs were and that seemed to immediately make Regina George calm as well. While she was a touch nervous during her stay they provided constant updates and pictures. We were completely relaxed and secure knowing she was being taken care of. You could tell they were true dog lovers! Highly recommended for others. Looking forward to her next visit with them!

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Corey B.
Sitter Profile Image: Nancyanne S.
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Nancyanne S.
from
$58
per night
5.0 out of 5 stars
125 reviews
60 repeat clients
2 years of experience
Wilmette, IL, 60091

We used to leave our dog at a large dog boarding place when traveling, and she would be grouped with so many different dogs that I can tell she was traumatized and often took days to be back to her normal carefree self (and she would have dog drooling all over her). This time under Nancyanne’s care our dog was able to stick to a routine similar to at home, and I can tell she was quite comfortable and after 9 days it was seamless that her demeanor was like she never left home. We would happily recommend Nancyanne to anyone who needs help.

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Jieying Z.
Sitter Profile Image: Laura & Vladimir H.
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Laura & Vladimir H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
76 reviews
17 repeat clients
10 years of experience
Niles, IL, 60714

Laura and Vldimir were great host and I can tell Ruby enjoyed her stay while she was there. They also sent out photos so I can see how Ruby was doing while she was staying with them. I would totally book them again for Ruby.

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Sunyoung T.
Sitter Profile Image: Janette & Charles S.
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Janette & Charles S.
Star Sitter
from
$50
per night
5.0 out of 5 stars
117 reviews
56 repeat clients
12 years of experience
Edison Park, Chicago, IL, 60631

Janette and Charlie watched our dog for the first time last week while we were on vacation. They were flexible with our schedule, and sent lots of pictures and videos so we could keep up on how Sadie was doing. She had a great week with them!

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Amy B.
Sitter Profile Image: Marija J.
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Marija J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
20 reviews
14 repeat clients
30 years of experience
Edison Park, Chicago, IL, 60631

Marija was amazing! She sent a lot of pictures and updates during Rookie’s entire stay. It was so nice knowing she was safe and getting a lot of love while we were gone!

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Elana B.
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Cat caregivers near you - Winnetka

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: Madeline I.
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Madeline I.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
4 reviews
4 repeat clients
3 years of experience
Wilmette, IL, 60091

About: I’ve been around dogs my entire life, mostly chihuahuas and rescues, so I’m very comfortable with pups who need a little extra patience, reassurance, or understanding. My hands-on experience goes far beyond casual pet care. At Miami University, I was part of Paws for a Cause, where we helped train dogs to prepare them for working with children or future companion roles. This gave me a strong foundation in obedience training, reading body language, and supporting dogs with different temperaments. More recently, I’ve been volunteering with the Evanston Animal Shelter, working with dogs who have a wide range of behaviors and needs. There, I’ve assisted with medication administration, training sessions, enrichment, and helping nervous or high-energy dogs feel more comfortable and confident. I’m also on a path toward becoming a Physician Assistant, which adds to my calm, attentive, and health-focused approach. I’m comfortable managing routines, monitoring for changes, and making sure each dog feels safe and cared for. Overall, I bring a mix of lifelong experience, formal training exposure, shelter work, and genuine love for dogs of all personalities. Your pet will be treated with patience, structure, and plenty of affection. I work full-time as a medical scribe during the day (9–5), so evenings, weekends, and holidays are when I’m most available for pet care. During those times, I’m fully focused on your pet’s needs—whether that’s walks, playtime, feeding, or just keeping them company. My schedule outside of work is very flexible, so I can reliably fit in consistent visits or longer stays. When I’m caring for pets in a client’s home, I follow their normal routine as closely as possible—feeding schedules, walk times, crate routines, and any training cues you use. I take time to get to know your pet’s personality, comfort level, and boundaries so they feel safe and relaxed. I provide plenty of attention, enrichment, and calm companionship, and I always keep water fresh, watch for behavior changes, and send regular updates so you feel connected. If I’m hosting in my home (or doing extended stays), I make sure pets have a quiet, clean space to settle in, regular potty breaks, structured playtime, and a consistent routine. Safety is a top priority, doors secured, no access to anything unsafe, and lots of supervised time. Whether I’m in your home or mine, your pet gets patient, reliable care with the goal of making them feel comfortable, understood, and well-loved.

Sitter Profile Image: Donna C.
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Donna C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
577 reviews
137 repeat clients
40 years of experience
Wilmette, IL, 60091

Donna and Stephen were an absolute pleasure to work with! You can tell they truly love animals. We were very skeptical to leave our 2 cats with anyone but us, but immediately after meeting Donna and Stephen we knew our cats would be in great hands. They were very responsive and provided so many photos that brought us comfort while we were out of town. Will definitely be working with them in the future and would happily recommend them to anyone!

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Vanja S.
Sitter Profile Image: Katie S.
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Katie S.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
42 reviews
10 repeat clients
11 years of experience
Winnetka, IL, 60093

Katie is a wonderful cat-sitter! She was very responsive and kept me up to date daily with how my cat was doing at home. I would definitely ask her to cat-sit in the future and recommend you do the same.

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Garrett M.
Sitter Profile Image: Shailyn S.
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Shailyn S.
from
$12
per visit
5.0 out of 5 stars
4 reviews
5 years of experience
Evanston, IL, 60201

About: I’ve loved cats since I was a kids, mainly had outdoor but as soon as I could I adopted my baby from a shelter and we’ve been best friends since. I have also worked in a cat shelter before and know how to handle all the different personalities that kitties can have.

Sitter Profile Image: Jason A.
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Jason A.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
79 reviews
20 repeat clients
25 years of experience
Winnetka, IL, 60093

Jason stayed at our home with our cat for a week - it was great to know our kitty was so cared for, and that our house was watched over as well. Jason kept in touch all week, and we absolutely loved the pictures he sent each day! We’ll definitely have Jason back next time we travel!

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Leanne L.
Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

Absolutely recommend Rebeca! You can tell she really cares about dogs and loves what she does. My dog Snoopy has anxiety & is very shy at first but he felt at ease with her as soon as he met her during the meet and greet. She was so gentle, patient & sweet with him right away. I felt completely at ease knowing he was in such caring hands. I will def be booking with her again!

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Elaine D.
Sitter Profile Image: Andrew N.
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Andrew N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
64 reviews
19 repeat clients
15 years of experience
Evanston, IL, 60201

Andrew stayed in our home for a week He took good care of the litter boxes snd was respectful of the space. His very laid back, “chill” demeanor was perfect for our 2 cats. Andrew was very also observant and in tune with their needs and moods. He contacted me on a regular basis and sent me photos of his little charges. We intend to use his services again and highly recommended him to anyone in need of a cat sitter.

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Jane H.
Sitter Profile Image: Keeley V.
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Keeley V.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
16 reviews
5 repeat clients
15 years of experience
Wilmette, IL, 60091

We are so happy to have found Keeley to care for our cat. Keeley is very attentive and sends lots of updates and pictures. Highly recommend Keeley!

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Allison D.
Sitter Profile Image: Ella V.
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Ella V.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
281 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

Ella did a great job feeding, playing with, and hanging out with my cat. She also cleaned the kitty litter which was wonderful. She sent daily photos of everything which was great too. Thanks Ella.

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Steve B.
Sitter Profile Image: Angie F.
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Angie F.
from
$18
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
7 years of experience
Winnetka, IL, 60093

About: I’ve been a dedicated cat owner since childhood and have cared for cats my entire life, giving me deep experience with feline behavior, routines, and needs at every stage of life. In addition to caring for my own cats, I’ve also provided reliable cat sitting services for friends, family, and other pet owners, including feeding, litter box maintenance, playtime, administering basic care, and ensuring cats feel safe and comfortable while their owners are away. I understand that every cat has a unique personality, and I’m patient, attentive, and committed to providing loving, stress-free care for both playful kittens and senior cats.

Sitter Profile Image: Julia S.
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Julia S.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
17 reviews
5 repeat clients
15 years of experience
Evanston, IL, 60201

Julia was able to help us within relatively short notice (~1 week before we left for our trip) and was communicative and friendly throughout. She came out a few days before our trip to do a complimentary "meet-and-greet" to go over instructions, meet our cats, and generally put us at ease since it was our first time using a sitter via Rover. We looked forward to receiving her daily updates and pictures, and appreciated how she communicated proactively when minor questions came up.

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Max M.
Sitter Profile Image: Leah G.
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Leah G.
from
$23
per visit
5.0 out of 5 stars
43 reviews
14 repeat clients
8 years of experience
Morton Grove, IL, 60053

Leah took great care of our super senior kitty who is as high maintenance as she is affectionate. Leah gave her meds and snuggles shared photos of each visit and is one of our go-to sitters. Highly recommend!

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Rebecca S.
Sitter Profile Image: Jake L.
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Jake L.
from
$9
per visit
4 years of experience
Northbrook, IL, 60062

About: I’ve been around dogs and cats all my life, recently worked with animals as big as horses and cows, to chickens and ducks. Friends and family trust me with their animals! My schedule is currently free, weekdays and weekends and nights! I am willing to work holidays. I will also walk in any type of weather! I have a fenced in backyard, with 2 very friend dogs for yours to play with! I do have crates (if needed) and lots of treats!

Sitter Profile Image: Emily L.
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Emily L.
from
$20
per visit
5.0 out of 5 stars
29 reviews
16 repeat clients
10 years of experience
Skokie, IL, 60077

Emily was absolutely incredible. She went far above and beyond and we couldn’t be happier. I think the cats were actually a bit sad to see us come home instead of Emily 😂

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Kelly O.
Sitter Profile Image: Isabela B.
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Isabela B.
from
$16
per visit
5.0 out of 5 stars
27 reviews
10 repeat clients
15 years of experience
Glenview, IL, 60025

I am extremely happy with Isabela and her care of our two cats. We were away for close to two weeks and I was initially nervous about being gone that long. But, she took great care of them and sent daily updates and photos. I would highly recommend her and would be happy to use her again.

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Deborah P.
Sitter Profile Image: Stephen M.
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Stephen M.
from
$25
per visit
5.0 out of 5 stars
39 reviews
16 repeat clients
15 years of experience
Winnetka, IL, 60093

Stephen was excellent and communicated and sent photos and updates! Our cat was so well cared for. Highly recommend!

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Catherine D.
Sitter Profile Image: Cicely B.
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Cicely B.
from
$18
per visit
5.0 out of 5 stars
2 reviews
10 years of experience
Winnetka, IL, 60093

Riley loved it! Thanks for coming over!!

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Jeff U.
Sitter Profile Image: Melissa V.
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Melissa V.
from
$18
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Wilmette, IL, 60091

Melissa did a fine job with my cat. She seems to love animals and is reliable. Highly recommend!

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Laurie K.
Sitter Profile Image: Sidney P.
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Sidney P.
from
$27
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Winnetka, IL, 60093

About: I love Cats & Kittens. My girlfriend & I have 10+ years of experience with animals of all types. We have no animals of our own but we love them as if they were ours

Sitter Profile Image: Maggie J.
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Maggie J.
from
$16
per visit
11 years of experience
Winnetka, IL, 60093

About: I’ve always had a cat in my household, and when I was 12 I got my own cat! I have been fully responsible for her for 6 years, and that has taught me so much about cat care. I have also taken care of many other cats, so I am no stranger!

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Perfect for high energy dogs - Winnetka

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: Naomi & Johann J.
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Naomi & Johann J.
Star Sitter
from
$40
per day
5.0 out of 5 stars
12 reviews
4 repeat clients
15 years of experience
Glenview, IL, 60025

Naomi & Johann J. will always be our 1st choice to watch Javy whenever we need to leave him with anyone. They sent many photos and reassuring messages about Javy’s eating all of his food…he wouldn’t have eaten anything, had he been stressed about being there. Wonderful pup watchers!

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Lian E.
Sitter Profile Image: Lauren & Lauren P.
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Lauren & Lauren P.
Star Sitter
from
$40
per day
5.0 out of 5 stars
166 reviews
32 repeat clients
4 years of experience
Northbrook, IL, 60062

Lauren and Lauren are awesome! They care so much about dogs and want to make sure they’re comfortable and having fun. They were very accepting of Zoey’s high energy and the fact that she’s a puppy. I always feel good dropping Zoey off for daycare here.

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Rachel S.
Sitter Profile Image: Kazuhiro & Akemi S.
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Kazuhiro & Akemi S.
Star Sitter
from
$60
per day
5.0 out of 5 stars
203 reviews
54 repeat clients
35 years of experience
Wilmette, IL, 60091

Kazuhiro and Akemi were fantastic with Bailey as usual. They sent multiple updates and photos all throughout the day. Bailey is given a lot of attention and love. Highly recommend them anytime!

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Sangita K.
Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$50
per day
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

If you need a reliable, flexible, and kind pet sitter, look no further than Rebeca. She took my pups on short notice and didn't blink an eye when I realized I had accidentally booked a 2-hour visit instead of 14 hours. She was happy to keep them the whole day, communicated proactively with fun updates and photos, and gave them access to a massive fenced-in yard that they absolutely loved. She made a stressful booking mistake completely stress-free. Thank you, Rebeca!

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Joseph S.
Sitter Profile Image: Claire C.
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Claire C.
Star Sitter
from
$42
per day
5.0 out of 5 stars
7 reviews
3 repeat clients
30 years of experience
Morton Grove, IL, 60053

Claire is a standout. She communicates timely and effectively, is polite and professional, organized and most importantly she is incredible with dogs. Claire documented walks including duration, route and distance, and meals including time, amount of food eaten by each dog. Her feedback on my dogs' personality traits was spot on as well, demonstrating her care and attention. I would wholeheartedly recommend Claire to anyone in need of a trustworthy sitter. THANK YOU, CLAIRE!

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Joseph S.
Sitter Profile Image: Rizwan & Noorjahan M.
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Rizwan & Noorjahan M.
Star Sitter
from
$30
per day
5.0 out of 5 stars
42 reviews
10 repeat clients
6 years of experience
Morton Grove, IL, 60053

This is the first time we’ve had someone (who is not our family) watch our dog. I was very nervous especially be in Poppy is young - she’s just a year old. Noor watched Poppy for a day. Noor was so patient with her - poppy was initially apprehensive to go in their house, but Noor took her time to ensure Poppy was comfortable. Noor asked questions about feeding, walks, general behavior & preferences. this put me at ease knowing she was thinking these. We did this trial daycare in preparation for a longer stay for Poppy later this year. Noor was also very communicative with texts and also a video! We were happy with the care poppy received and plan to book with Noor again!

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Mimi D.
Sitter Profile Image: Lee & Niv D.
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Lee & Niv D.
Star Sitter
from
$49
per day
5.0 out of 5 stars
180 reviews
79 repeat clients
14 years of experience
Wilmette, IL, 60091

Our long time sitter is moving out of the area and we were so concerned that we would never find someone as comparable and we did. Lee and Niv are awesome, caring and we feel completely confident leaving our little Jack with rhem

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Mary S.
Sitter Profile Image: Cynthia A.
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Cynthia A.
Star Sitter
from
$50
per day
5.0 out of 5 stars
71 reviews
24 repeat clients
25 years of experience
EVANSTON, IL, 60202

Cynthia was welcoming, communicative, professional, and genuinely cares about the dogs in her care. It was great to see the dogs playing together and enjoying her house and yard, so we'd absolutely have her dog sit for us again!

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Richard B.
Sitter Profile Image: Cheri R.
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Cheri R.
Star Sitter
from
$55
per day
5.0 out of 5 stars
191 reviews
86 repeat clients
30 years of experience
Evanston, IL, 60202

Toby's second time with Cheri. Sounded like it was a good day again, weather was nice so sounds like they got to spend a lot of time outside. Thanks

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Jon P.
Sitter Profile Image: Julie T.
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Julie T.
Star Sitter
from
$45
per day
5.0 out of 5 stars
46 reviews
16 repeat clients
30 years of experience
Highland Park, IL, 60035

Julie has been an accommodating and loving caregiver to our Bella. Bella really seems to enjoy her time at Julie's place. She will be our first-choice sitter whenever we need a caregiver for Bella. Thank you Julie!

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Robbie H.
Sitter Profile Image: Carly S.
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Carly S.
from
$63
per day
5.0 out of 5 stars
38 reviews
11 repeat clients
20 years of experience
Near West Side, Northfield, IL, 60093

Carly was great with Willis! She sent pictures throughout the stay and provided regular updates. She was flexible with timing too which I really appreciated. Definitely recommend!

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Elise R.
Sitter Profile Image: Whitney O.
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Whitney O.
Star Sitter
from
$38
per day
4.9 out of 5 stars
100 reviews
36 repeat clients
31 years of experience
Rogers Park, Chicago, IL, 60626

My 4mo puppy Nova had a BLAST at Whitney’s with her pup. She came home super tired from all the play which was great for me & my cat bc we got lots of rest that night! ? she slept the car ride home & went straight to sleep for the night when we got in. I’m so glad she got to get out some of that energy & I feel like Nova was in great hands while I was away at work. & she was only 10min away from where I live & is right off the expressway which was super convenient. We will definitely be using Whitney’s services again!

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Sharon B.
Sitter Profile Image: Sandra & Sorin A.
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Sandra & Sorin A.
from
$55
per day
5.0 out of 5 stars
38 reviews
19 repeat clients
5 years of experience
Skokie, IL, 60076

Sandra and her family were wonderful! She sent a video and picture of Bitsy. She also let Bitsy lay across her neck and watch her work. Thank you for being so kind and gentle with my dog. I would highly recommend this family!

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Anne J.
Sitter Profile Image: Danielle & Ryan H.
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Danielle & Ryan H.
from
$40
per day
5.0 out of 5 stars
8 reviews
1 repeat client
21 years of experience
Highland Park, IL, 60035

Danielle and Ryan were the best sitters for Wally. They sent tons of pictures, kept us updated, and gave Wally constant attention. Strongly recommend them!

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Jed S.
Sitter Profile Image: Ella V.
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Ella V.
Star Sitter
from
$80
per day
5.0 out of 5 stars
281 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

Ella is absolutely amazing! She took the best care of Walter and he felt right at home. I’m very appreciative of all that she’s done! I wholeheartedly recommend having her watch your fur babies.

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Olivia S.
Sitter Profile Image: Andrew G.
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Andrew G.
Star Sitter
from
$55
per day
5.0 out of 5 stars
233 reviews
75 repeat clients
20 years of experience
Skokie, IL, 60076

I really like Andrew’s set up, spacious house with a fensed in yard, all accessible to the dogs. I enjoyed meeting him and his lovely family, and felt very comfortable leaving my puppy there. He came back happy and tired!

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Jane A.
Sitter Profile Image: Patricia A.
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Patricia A.
Star Sitter
from
$50
per day
5.0 out of 5 stars
64 reviews
14 repeat clients
7 years of experience
Skokie, IL, 60076

Freddie had fun hanging out at daycare today. Thank you for dropping him off to me too!!!

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Traci M.
Sitter Profile Image: Ryan B.
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Ryan B.
from
$50
per day
5.0 out of 5 stars
17 reviews
1 repeat client
15 years of experience
Northfield, IL, 60093

Ryan was amazing! He took such great care of Benny and treated him like his own dog. He kept me updated throughout the day with pictures and videos. Benny loved playing with Crosby and was totally pooped when I picked him up (he slept great - the sign of a fun filled day). Would definitely recommend Ryan!

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Halia P.
Sitter Profile Image: Marissa H.
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Marissa H.
from
$45
per day
5.0 out of 5 stars
7 reviews
3 repeat clients
20 years of experience
Evanston, IL, 60201

About: I ensure they receive the attention and provide expert supervision and ensure that every dog receives the highest level of and go beyond basic boarding by offering a variety of enrichment activities to keep your dog mentally and physically stimulated. From interactive toys and puzzles to group play sessions and nature walks, providing a range of activities to keep your dog happy and engaged. Clean and Safe Facilities: I follow strict cleanliness protocols to prevent the spread of illness and ensure a comfortable stay for every guest. Communication and Updates: I understand how important it is to stay connected with your pet while you're away… regular updates and photos so you can see how much fun your dog is having during their stay I am available all the time. I am very flexible and take my job and care seriously! Any medications or food allergies will be given priority. I have a fenced in yard with security for my surroundings and your pets. I also have a large crate as well and try to ensure safety first

Sitter Profile Image: Karissa D.
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Karissa D.
from
$50
per day
15 years of experience
Winnetka, IL, 60093

About: I’ve cared for animals most of my life. I had a cat for 15 years and a puppy for several years growing up. I’m comfortable with different ages and personalities, and I always treat pets with the same patience and love I’d want for my own. I work from home full-time, which gives me a flexible schedule and allows me to provide attentive care throughout the day. I’m available for doggy daycare during working hours, including regular potty breaks, playtime, feeding, and companionship. I’m also available for walks and drop-in visits after 5:00 PM on weekdays. With me, pets get a calm, safe, and welcoming space. I’ll make sure they have plenty of attention, regular potty breaks, playtime, and a cozy spot to relax. I follow your pet’s routine closely so they feel comfortable and at ease.

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Adventure-ready dog walkers - Winnetka

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: Madeline I.
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Madeline I.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
4 reviews
4 repeat clients
3 years of experience
Wilmette, IL, 60091

Medalin was great with our difficult dog

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Alon F.
Sitter Profile Image: Donna C.
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Donna C.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
577 reviews
137 repeat clients
40 years of experience
Wilmette, IL, 60091

Donna was great to our puppy. She is communicative and trust wordy. Our little ball of energy would come tired from a walk. Definitely would use her again. Thank you Donna

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Samir C.
Sitter Profile Image: Ella V.
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Ella V.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
281 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

Thank you Ella for walking our two pups while we traveled to Greece!!!We loved getting daily updates with photos while we were gone!!You were such a gift to us that we could travel with the comfort knowing they were so well cared for!!!🐶🐶💖💖

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Sharon M.
Sitter Profile Image: Jason A.
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Jason A.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
79 reviews
20 repeat clients
25 years of experience
Winnetka, IL, 60093

Jason was on time and took good care of our big dog on all of his walks. This was a repeat booking for us, and we’ll continue reaching out to him!

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Christa H.
Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

About: I’ve been around dogs my whole life and have spent the past few years helping care for all sorts of fur babies ! I’ve helped with dog walks, drop-ins, pet sitting, and spending time with dogs of all breeds, sizes, and personalities. I’m obsessed with all fur babies and I’m very comfortable handling all sizes and all breeds! We don’t discriminate😆 I am super accommodating! I love going on walks and how cute to have a little companion to get my steps in with! Over the years I’ve learned how important patience, consistency, and love are when it comes to caring for animals. I always make sure every fur baby feels safe, comfortable, and well cared for while their owners are away. Spending time with animals is something I genuinely enjoy, and I treat every single one like they’re my own.

Sitter Profile Image: Anna D.
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Anna D.
from
$26
per walk
4.9 out of 5 stars
38 reviews
16 repeat clients
16 years of experience
Winnetka, IL, 60093

Anna is amazing! She has been walking our pup every day for the past few months. Anna not only walks Charlie but actually spends time playing with him and training him - she even taught him the paw command! Anna sends very detailed reports and lots of cute pictures after every walk. Being first time puppy owners we feel so lucky to have Anna looking after our pup!

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Katie A.
Sitter Profile Image: Alexis B.
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Alexis B.
Star Sitter
from
$30
per walk
4.9 out of 5 stars
110 reviews
57 repeat clients
15 years of experience
Evanston, IL, 60201

Alexis was great, professional communication, prompt, personable, and confident with Winnie. She took Winnie on a good long walk as she said she would. Very professional, would be happy to use her again!!

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Sarah C.
Sitter Profile Image: Stephen M.
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Stephen M.
from
$30
per walk
5.0 out of 5 stars
39 reviews
16 repeat clients
15 years of experience
Northbrook, IL, 60062

Stephen is an incredible dog sitter and walker! He is incredibly professional, caring and attentive. We loved getting photos of our dog after each visit - both action shots and close ups. We are grateful for Stephen's attention to detail, professionalism and care.

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JANE S.
Sitter Profile Image: Mia W.
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Mia W.
from
$22
per walk
5 years of experience
Wilmette, IL, 60091

About: I have experience working with cats and dogs. My family adopted a cat a few years ago and she quickly became part of the family. I have experience walking my neighbors dogs and know how to tame a dog if need be. Working with cats and dogs is a passion of mine as each has their own unique personality that is discovered over time. I am a college student at the Royal Conservatory of Music Glenn Gould School. I am available most afternoons Monday to Saturday, except for Sunday. I have a large fenced backyard that is safe for dogs to soak up the sun while having fun exploring, running around, and playing games

Sitter Profile Image: Phoenix B.
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Phoenix B.
from
$20
per walk
4.9 out of 5 stars
30 reviews
15 repeat clients
25 years of experience
Glenview, IL, 60026

Caroline is so dependable and truly great with dogs. Sue absolutely loves our dog and he looks so forward to playing with her. I have complete trust in her knowing Cody is in great hands.

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Rosie G.
Sitter Profile Image: Isabela B.
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Isabela B.
from
$20
per walk
5.0 out of 5 stars
27 reviews
10 repeat clients
15 years of experience
Glenview, IL, 60025

Isabella is super friendly and caring with Theo. She always leaves a summary of their walk. I will definitely continue to have her walk Theo!

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rebecca s.
Sitter Profile Image: Jonah B.
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Jonah B.
from
$18
per walk
10 years of experience
Evanston, IL, 60201

About: I’m naturally very active, so if your dog loves long walks and plenty of playtime, they’ll have a great workout buddy with me. At the same time, I’m super patient and adaptable to whatever your pet needs. I’ve worked with all kinds of animals with different traits and can definitely meet your needs! Because I work a part-time job with a flexible schedule, pet care easily fits right into my daily routine. I can structure my shifts around your dog's specific needs, I have plenty of open windows to make your pet a top priority throughout the week. Whether I’m hosting your dog or staying at your place, my goal is to keep their routine exactly how they like it. For active pups, that means plenty of long walks and fresh air to burn off energy, while puppies get consistent potty breaks and training support. If you have a senior dog, I focus on a quiet, stress-free environment and precise feeding schedules. I adapt completely to your pet's needs.

Sitter Profile Image: Marissa H.
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Marissa H.
from
$19
per walk
5.0 out of 5 stars
7 reviews
3 repeat clients
20 years of experience
Wilmette, IL, 60091

Marissa did a great job with our hyper dog. She showed patience and sternness. Thank you

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stephen t.
Sitter Profile Image: Sidney P.
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Sidney P.
from
$30
per walk
5.0 out of 5 stars
12 reviews
3 repeat clients
15 years of experience
Winnetka, IL, 60093

Sidney and Ella accommodated changes to our schedule day by day necessitated by our medical adventure. One less thing to worry about. And the dog and they got on well.

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Lew B.
Sitter Profile Image: Andrew G.
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Andrew G.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
233 reviews
75 repeat clients
20 years of experience
Winnetka, IL, 60093

I highly recommend Andrew!!! We had to quickly set up regular dog waking with him due to an injury and he has been amazing with our very stubborn dog, taking her on long walks when we couldn't. We are really appreciative for his care and hope to schedule many more walks with him in the future!

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Kelsey C.
Sitter Profile Image: William G. H.
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William G. H.
from
$20
per walk
5.0 out of 5 stars
23 reviews
9 repeat clients
50 years of experience
Wilmette, IL, 60091

Bill is a reliable dog walker. He was great with our dog, Bella. He was flexible when adding extra walks last minute. He is also very responsive. I highly recommend his services to others.

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Donna J.
Sitter Profile Image: Riley K.
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Riley K.
from
$14
per walk
5.0 out of 5 stars
4 reviews
6 years of experience
Evanston, IL, 60201

About: I have been pet-sitting since I was 14, due to the population of dogs in my neighborhood. My community has trusted me with their fur babies, and I’m certain we will have so much fun!😊 I am currently working a part time job, so I won’t be available 24-7—but I am more than happy to work with you on times to be there for your pets :) Please book with only serious inquiries😊 In my clients home, I will follow all rules and guidelines relating not only to their pet, but also to respecting their space as well.

Sitter Profile Image: Maggie J.
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Maggie J.
from
$15
per walk
11 years of experience
Winnetka, IL, 60093

About: I have always had at least 2 animals in my house, which helped me learn how to be responsible at a young age. Then when I was older, I would help me neighbors and other friends when they went out of town, so I have been taking care of dogs/cats for a while! I am in college right now, so I will have some spare time to stop by/walk dogs. My class schedule is spread out nicely, so I will have more than enough time and flexibility. I will help your pets in your home, and try to follow their normal routine. I can crate, feed, walk, play, anything you could ever need!

Sitter Profile Image: Juliette S.
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Juliette S.
from
$20
per walk
5.0 out of 5 stars
19 reviews
6 repeat clients
20 years of experience
Northfield, IL, 60093

Juliette is wonderful and responsible! My dog absolutely loved her! She took excellent care of my pup and also sent lots of adorable photos. :)

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Heather H.
Sitter Profile Image: Samantha P.
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Samantha P.
from
$25
per walk
4.7 out of 5 stars
28 reviews
12 repeat clients
5 years of experience
Glenview, IL, 60025

Great first experience with Samantha. Fast and easy communication. Milo is happy from his walk. I would definitely use her service again and recommend to others.

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Shin L.
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Over 980,000
dogs traded couch time for play time with Doggy Day Care on Rover1

Large dog specialists near you - Winnetka

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: Thao T.
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Thao T.
from
$45
per night
4.9 out of 5 stars
102 reviews
56 repeat clients
12 years of experience
Wilmette, IL, 60091

Thao was absolutely the right choice for us and Ginny! We have now found the person we will always use in the future. Thao is loving and caring with all the dogs she watches!

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Jim M.
Sitter Profile Image: Joerg & Lake Z.
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Joerg & Lake Z.
Star Sitter
from
$35
per night
5.0 out of 5 stars
184 reviews
67 repeat clients
12 years of experience
Edgewater, Chicago, IL, 60660

I have complete peace of mind when I leave Chico with Joerg and Lake Z. They are very loving and Chico has a blast when he is with them and Lizzy, the have become great buddies.

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Ana V.
Sitter Profile Image: Lauren G.
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Lauren G.
Star Sitter
from
$35
per night
5.0 out of 5 stars
22 reviews
7 repeat clients
20 years of experience
Niles, IL, 60714

Lauren, and her family, were so kind, communicative and caring for our old boy! We couldn’t have been happier with Aspen’s care and are so grateful he was in such great hands!

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Kileen C.
Sitter Profile Image: Merrick R.
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Merrick R.
Star Sitter
from
$55
per night
5.0 out of 5 stars
48 reviews
8 repeat clients
5 years of experience
Skokie, IL, 60076

Merrick took care of our dog for a long weekend. Communication was good and easy, and our dog came home afterwards very happy and settled. Very happy with this experience, and we will use Merrick again in the future.

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Reuben K.
Sitter Profile Image: Claire C.
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Claire C.
Star Sitter
from
$42
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
30 years of experience
Morton Grove, IL, 60053

Claire was wonderful with Hazel (older dog) and Sam (older cat). This was the first time we used a pet care service and we were very fortunate to find Claire. She is thoughtful, kind, skilled with dogs and cats, and an excellent communicator. Hazel can be reactive to other dogs on walks; Claire was familiar with the ractive dogs and managed it with well. She also messaged us once a day while we were away with details and pictures. We have already booked with Claire again.

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Christine D.
Sitter Profile Image: Gabriela E.
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Gabriela E.
Star Sitter
from
$55
per night
5.0 out of 5 stars
33 reviews
6 repeat clients
20 years of experience
Glenview, IL, 60025

Gabriela was so nice. Her lovely family took care of my super energetic dog and happy to help accommodate if there’s a last minute changes. Definitely recommended.

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Faye N.
Sitter Profile Image: Cheri R.
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Cheri R.
Star Sitter
from
$53
per night
5.0 out of 5 stars
191 reviews
86 repeat clients
30 years of experience
Evanston, IL, 60202

Cheri is an amazing pet sitter! My dog, Taffy, has a heart condition, and I was so relieved to find Cheri. She listened carefully to all my instructions, took detailed notes, and truly cared for Taffy. She sent updates while I was away, and when I returned, Taffy was happy and healthy. I highly recommend Cheri!

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John B.
Sitter Profile Image: Hannah F.
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Hannah F.
Star Sitter
from
$45
per night
5.0 out of 5 stars
116 reviews
43 repeat clients
9 years of experience
Wheeling, IL, 60090

Hannah was amazing with our 9‑month‑old puppy, Romeo! She took such good care of him, made sure he was fed on time, and went out of her way to keep him comfortable and happy while we were gone. She kept sending us the cutest pics and videos, which really helped us relax on our trip. Romeo clearly had the best time with her, and we’ll definitely be booking her again every time we need boarding for Romeo. Highly recommend her to any friends looking for a super sweet and reliable pet sitter!

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Sawan K.
Sitter Profile Image: Ella V.
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Ella V.
Star Sitter
from
$90
per night
5.0 out of 5 stars
281 reviews
117 repeat clients
15 years of experience
Winnetka, IL, 60093

We were thrilled with Rosie's stay with Ella. From the moment we arrived and Ella showed us around, Rosie felt so comfortable. She was welcomed to explore the apartment and snuggle into the sofa. Ella sent several updates with photos and we felt very confident Rosie was being well cared for - with much time for play and walks. We will definitely book with Ella again.

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Deborah L.
Sitter Profile Image: Rebeca A.
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Rebeca A.
Star Sitter
from
$70
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
15 years of experience
Wilmette, IL, 60091

Great experience overall. Rebeca was communicative, reliable, and took good care of my dogs. I felt comfortable while I was away and would happily book again.

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Robert G.
Sitter Profile Image: Sophie H.
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Sophie H.
Star Sitter
from
$44
per night
5.0 out of 5 stars
158 reviews
46 repeat clients
16 years of experience
Rogers Park, Chicago, IL, 60626

Sophie was so understanding and patient with our rescue dog who is afraid of new people and dogs. She kept us updated throughout his stay on how he was doing and sent photos. We felt like our boy was safe and secure while we were away. Thanks Sophie!!!!

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Rosemary C.
Sitter Profile Image: Meghan M.
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Meghan M.
from
$50
per night
5.0 out of 5 stars
1 review
15 years of experience
Northbrook, IL, 60062

Five very waggy stars for Meghan (and her sweet pup, Ralphie)! Meghan is absolutely incredible. From the moment we arrived, it was clear that she is a true dog lover with tons of experience, and she knew exactly how to make our dog feel safe, happy, and completely at home. Our dog was treated like a member of her family and had the time of his life playing with Ralphie and the other dogs. The adorable photos and videos gave us so much peace of mind while we were away...and honestly, I think he was a little sad to come home, which is probably the highest compliment a dog can give. We will absolutely book again. Weekend at Ralphie’s is officially dog-approved!

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Colleen C.
Sitter Profile Image: Jeffrey & Ron R.
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Jeffrey & Ron R.
from
$60
per night
5.0 out of 5 stars
41 reviews
14 repeat clients
49 years of experience
Evanston, IL, 60202

This was our first time our 6 year old dog, Kona, stayed over at another dog sitter's home. Our dog is anxious and slow to warm up to people. Jeff and Ron were very warm, welcoming, and patient with Kona. We received regular updates and pictures. Our dog was in good spirits when we picked him up. We will definitely contact Jeff and Ron in the future!

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Michaela C.
Sitter Profile Image: Cynthia A.
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Cynthia A.
Star Sitter
from
$65
per night
5.0 out of 5 stars
71 reviews
24 repeat clients
25 years of experience
EVANSTON, IL, 60202

Cynthia treats my dog like he’s her own, he always has a great time and I feel stress free knowing he’s with her! The best pup sitter around!

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Cole K.
Sitter Profile Image: Jonah B.
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Jonah B.
from
$32
per night
10 years of experience
Evanston, IL, 60201

About: I’m naturally very active, so if your dog loves long walks and plenty of playtime, they’ll have a great workout buddy with me. At the same time, I’m super patient and adaptable to whatever your pet needs. I’ve worked with all kinds of animals with different traits and can definitely meet your needs! Because I work a part-time job with a flexible schedule, pet care easily fits right into my daily routine. I can structure my shifts around your dog's specific needs, I have plenty of open windows to make your pet a top priority throughout the week. Whether I’m hosting your dog or staying at your place, my goal is to keep their routine exactly how they like it. For active pups, that means plenty of long walks and fresh air to burn off energy, while puppies get consistent potty breaks and training support. If you have a senior dog, I focus on a quiet, stress-free environment and precise feeding schedules. I adapt completely to your pet's needs.

Sitter Profile Image: Rico Raymundo A.
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Rico Raymundo A.
Star Sitter
from
$50
per night
5.0 out of 5 stars
26 reviews
10 repeat clients
11 years of experience
West Ridge, Chicago, IL, 60659

Rico did a great job taking care of our senior rescue dog, Fritz! He sent lots of pictures, was quick to respond when I asked a question, and was very tolerant of Fritz’s quirks . We could tell Fritz was treated like part of the family!

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Caitlin & James S.
Sitter Profile Image: Michelle R.
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Michelle R.
from
$50
per night
5.0 out of 5 stars
57 reviews
14 repeat clients
6 years of experience
Rogers Park, Chicago, IL, 60645

Michelle is the best! She provides updates, pictures, and our dog loves her! He’s usually nervous eating in new places but he thrives when he stays with her.

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Joanna S.
Sitter Profile Image: Marija J.
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Marija J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
20 reviews
14 repeat clients
30 years of experience
Edison Park, Chicago, IL, 60631

Marija was amazing! She sent a lot of pictures and updates during Rookie’s entire stay. It was so nice knowing she was safe and getting a lot of love while we were gone!

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Elana B.
Sitter Profile Image: Nicholas W.
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Nicholas W.
Star Sitter
from
$50
per night
5.0 out of 5 stars
18 reviews
2 repeat clients
10 years of experience
Albany Park, Chicago, IL, 60625

Nicky was great with our Frenchie. Lots of communication and photos. Would recommend if you need someone that can care for a fussy dog that needs lots of attention!

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Chris L.
Sitter Profile Image: Nicole G.
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Nicole G.
Star Sitter
from
$75
per night
5.0 out of 5 stars
28 reviews
16 repeat clients
25 years of experience
Highland park, IL, 60035

Nicole is so caring and communicative. I needed to find coverage for my pet while I was going on vacation. Nicole was very accommodating and kind to my dog Fia. She sent pictures and updates frequently, and Fia had a blast at her place.

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Lokesh P.
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