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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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1. Ashley M.

Rover 101
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
0.7 mi. away
5.0 out of 5 stars
44 reviews
19 repeat clients
from
$52
per night

After a quick move to out of state move to Chicago with a vacation already planned, we had to scramble to find somewhere for our dogs go. Our dogs stayed with Ashley for a full week and it was such a relief to know they were well taken care of. We received frequent pictures and updates during the week. One of our dogs is having a hard time adjusting to city life and Ashley was very accommodating and gracious with her. We will definitely be reaching out to Ashley again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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2. Tania B.

Rover 101
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
2.2 mi. away
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$50
per night

Tania was great with my little guy! He is an anxious pup and he seemed to do really well with her. She communicated throughout his stay, sent lots of pics, and was very accommodating. I will definitely be using her again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Andrew T.
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Sitter Profile Image: Andrew T.
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3. Andrew T.

WFH Couple, Park Nearby
Lower West Side, Chicago, IL, 60608
1.4 mi. away
5.0 out of 5 stars
102 reviews
42 repeat clients
from
$45
per night

Andrew and his wife were great! Very communicative, sent up dates the whole time. Would definitely book another stay for my pups in the future.

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

Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
1.6 mi. away
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$50
per night

Ann-Marie took great care of my fur baby while I was out of town. She sent pictures throughout the stay, maintained communication, and was flexible when we pushed our return to a later time. I would definitely recommend her and look forward to hiring her again in the future.

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Sitter Profile Image: Gillian K.
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Sitter Profile Image: Gillian K.
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5. Gillian K.

Loves long walks and fluffy friends
Bridgeport, Chicago, IL, 60608
0.8 mi. away
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$40
per night

Our third time using Gillian’s pet sitting services and it was fantastic as usual! My dog is always so happy to come here, and Gillian does such a great job keeping us posted with silly photos. This time around my dog decided to hurt her paw days before my trip, but Gillian put my mind at ease with following her new medication routine and giving me updates on how her paw was doing.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jennifer N.
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Sitter Profile Image: Jennifer N.
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6. Jennifer N.

Not Just a pet,a family favorite.
Lower West Side, Chicago, IL, 60608
1.7 mi. away
5.0 out of 5 stars
107 reviews
62 repeat clients
from
$50
per night

You can tell they really care about your dog, and treat them like a family member. We will definitely be using their service again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jason M.
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Sitter Profile Image: Jason M.
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7. Jason M.

Experienced Professional
Lower West Side, Chicago, IL, 60608
0.6 mi. away
from
$50
per night

Jason is a very knowledgeable dog owner and from what we have noticed has maintained clients for decades, we trust Jason 100% with our senior dog Hannah who is very particular about who she socializes with. Jason is aware of this and knows to keep her away from other dogs as she can be reactive sometimes. Jason absolutely loves dogs and is familiar with all the ones in our neighborhood, to have Jason as a friend and neighbor is to know all the four-legged friends that hang along with him and that’s not a bad way to live <3

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Briana V.
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Sitter Profile Image: Briana V.
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8. Briana V.

Always home, 24/7 attention & care!
South Lawndale, Chicago, IL, 60623
3.5 mi. away
5.0 out of 5 stars
46 reviews
12 repeat clients
from
$48
per night

Briana is attentive, transparent, and honest. My dog randomly started bleeding at her house due to a sudden prostate issue and Briana communicated with me immediately. She even fed him a special diet while I tried to figure out what was going on with him. We eventually had to take him to the emergency ER, but She was awesome during the trouble shooting. If you like working with people who have strong character and a moral compass, Briana is your girl.

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Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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9. Katie M.

Long time animal lover
Near North Side, Chicago, IL, 60610
4.2 mi. away
5.0 out of 5 stars
160 reviews
54 repeat clients
from
$45
per night

Katie was amazing and took great care of my pups needs and provided updates during a longer stay. Java was very welcoming as well, and we look forward to booking next time with them.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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10. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
3.1 mi. away
5.0 out of 5 stars
245 reviews
106 repeat clients
from
$45
per night

Elizabeth and her family were amazing with Penny! I got plenty of photos and updates and Elizabeth even sent us home with some dental treats. I would trust Elizabeth with Penny again without a doubt.

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Sitter Profile Image: Dion F.
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Sitter Profile Image: Dion F.
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11. Dion F.

Your baby’s favorite hotel 🐕🦴
Near West Side, Chicago, IL, 60661
2.2 mi. away
5.0 out of 5 stars
6 reviews
from
$50
per night

It’s always a little nerve wracking when you’re away from your pup for an extended period, but Dion was great with Brix! He was patient, kind, communicative and gave him plenty of long walks which we appreciate. Will be utilizing Dion in the future when needed :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Georgia M.
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Sitter Profile Image: Georgia M.
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12. Georgia M.

Love to pet sit and going for walks
Near North Side, Chicago, IL, 60610
3.3 mi. away
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$35
per night

Georgia was great! She was flexible, able to accommodate a last minute request and was very communicative. She sent some cute pictures of my pup and I could tell she had a good time! Would definitely feel great having her watch my pup again. Thanks Georgia!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Fatimah A.
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Sitter Profile Image: Fatimah A.
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13. Fatimah A.

Rover 101
WFH caring & fun dog mom
Near West Side, Chicago, IL, 60612
2.6 mi. away
5.0 out of 5 stars
191 reviews
73 repeat clients
from
$55
per night

Fatimah was our first Rover boarding experience and she was great. She sent frequent pictures and video and our dog Violet clearly had a great time. Highly recommend!

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Sitter Profile Image: Regan D.
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Sitter Profile Image: Regan D.
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14. Regan D.

Your friendly neighborhood pet girl
Near North Side, Chicago, IL, 60654
2.9 mi. away
5.0 out of 5 stars
34 reviews
13 repeat clients
from
$45
per night

Regan and Adam are always so kind and proactive when it comes to communication. I appreciate their frequent updates with photos and know that Hootie always comes home happy. Would recommend!

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Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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15. Rachel W.

Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
1.6 mi. away
5.0 out of 5 stars
41 reviews
16 repeat clients
from
$65
per night

Rachel was AMAZING!! She took such great care of our Shelby. She was extremely accommodating with drop off and pick up. Rachel's dog, Addy, was so sweet and Shelby enjoyed her time with her. We hope Rachel is available the next time we are out of town.

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Sitter Profile Image: Joanna K.
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Sitter Profile Image: Joanna K.
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16. Joanna K.

WFH Artist and Lifelong Dog Lover!
Lower West Side, Chicago, IL, 60608
1.3 mi. away
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$40
per night

Joanna was very attentive and took great care of our boxer,Lola! She sent pics regularly of walks, activities, playtime at the park and snuggles. My Lola was happy and even has another dog that was boarding the same week to play with. I highly recommend Joanna and will definitely use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Nate N.
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Sitter Profile Image: Nate N.
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17. Nate N.

Nurture, Bond and Train!
Near West Side, Chicago, IL, 60612
2.3 mi. away
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night

Nate was great with my active almost 10 year old. Took her on multiple walks daily even in the rain and was very communicative sending pictures snd comments regularly. Will leave her with him again and not worry about her at all.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Melanie S.
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Sitter Profile Image: Melanie S.
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18. Melanie S.

Experienced Dog Owner and Dog Lover
Near North Side, Chicago, IL, 60654
3.0 mi. away
5.0 out of 5 stars
157 reviews
60 repeat clients
from
$55
per night

Melanie was great! Penny has very bad separation anxiety and Melanie was more than accommodating to her needs. She kept me updated on how Penny was doing and gave her lots of love!

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Sitter Profile Image: Ruben M.
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Sitter Profile Image: Ruben M.
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19. Ruben M.

Loving care when you're not there.
Humboldt Park, Chicago, IL, 60651
5.3 mi. away
5.0 out of 5 stars
79 reviews
33 repeat clients
from
$50
per night

Ruben was amazing! He went above and beyond to make sure Kodak enjoyed his time there and was taken care of. Great communication, he responds quickly & I received pictures & updates throughout the day & evening. Kodak got a long well with his dogs and enjoyed playing with them! When I picked him up Ruben gave me a thank-you bag with a handwritten note (it was so sweet) & a squeaker toy for Kodak. I will definitely be booking with him again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Daniel A.
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Sitter Profile Image: Daniel A.
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20. Daniel A.

All Dogs Are Perfect
Near West Side, Chicago, IL, 60607
1.8 mi. away
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$60
per night

Daniel was amazing! He gave me lots of updates and helped my pup feel right at home. We would definitely leave Stella with him and Benji again

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