Dog Boarding in Grand Crossing, Chicago

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Sitter Profile Image: Ashley R.
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Sitter Profile Image: Ashley R.
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1. Ashley R.

WFH Cat lady❤️dog lover
Woodlawn, Chicago, IL, 60637
1.8 mi. away
Boarding, Doggy Day Care
from
$35
per night
5.0 out of 5 stars
4 reviews
Profile image

Ashley is the greatest!! I was a little worried about leaving my kitten Hadley for two weeks, but he immediately settled into her home and it was clear from the pictures and videos she sent of him always at her side and playing with her cat Pepsi that he adored both of them. Ashley sent me pictures and kept me updated every day, was so accommodating of my schedule and Hadley's routine, and gave him lots of attention. She was super easy to coordinate and communicate with, Hadley settled back in with me as though I’d never left, and I’ve already booked his next stay with her :)

Availability updated today
Sitter Profile Image: Bola A.
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Sitter Profile Image: Bola A.
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2. Bola A.

Star Sitter
Big time dog lover 😄
Hyde Park, Chicago, IL, 60615
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$49
per night
5.0 out of 5 stars
85 reviews
23 repeat clients
Profile image

She was fantastic and so helpful. Best with pics and updates. Thank you for taking care of my boy. Will definitely be letting my man stay with you again.

Availability updated 3 days ago
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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3. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5.0 out of 5 stars
289 reviews
128 repeat clients
Profile image

Couldn’t have asked for a better sitter for my big baby Maxwell!!!!!!! E and Neil never disappoint with taking care of him! Even out of the country for 7 days I would get updates!!A++++++ highly recommend. Communication was amazing!

Availability updated yesterday
Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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4. Kyle H.

Rover 101
Star Sitter
Almost 20 years of experience!
Hyde Park, Chicago, IL, 60615
2.8 mi. away
Boarding
from
$55
per night
5.0 out of 5 stars
24 reviews
5 repeat clients
Profile image

Best ever situation for Molly. Will use again every time. Molly has had anxiety issues with both in-my-home boarding, kennels, and other individual services. Kyle (and her husband, Ben) are tremendously wise, easy going, experienced.

Availability updated 3 days ago
Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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5. Kayla S.

Star Sitter
✨Furry Earth Angels Wanted 🐈‍⬛🐕
Kenwood, Chicago, IL, 60615
3.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$49
per night
5.0 out of 5 stars
43 reviews
21 repeat clients
Profile image

This was our second time staying with Kayla and it was just as great as the first! Highly recommend! She is very caring and goes above and beyond!

Availability updated yesterday
Sitter Profile Image: Dwight C.
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Sitter Profile Image: Dwight C.
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6. Dwight C.

Rover 101
Star Sitter
Work from home - large fenced yard
Woodlawn, Chicago, IL, 60637
1.3 mi. away
Boarding, Doggy Day Care
from
$30
per night
5.0 out of 5 stars
172 reviews
67 repeat clients
Profile image

Dwight sent text messages and pictures of Bella, which I looked forward to, the communication helped to assure me that Bella was doing well. I could tell that Bella enjoyed her stay!!

Availability updated 9 days ago
Sitter Profile Image: Marchauna B.
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Sitter Profile Image: Marchauna B.
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7. Marchauna B.

We provide full-time pet services!
Roseland, Chicago, IL, 60620
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
55 reviews
13 repeat clients
Profile image

Marchauna and her partner were phenomenal! Sent pics and videos almost everyday during the 7-day booking, provided updates on how my pet was doing in her new environment, and even made it possible for me to do early pickup on short notice. 10/10 would recommend and I will be rebooking in the future, thank y’all!!

Availability updated 3 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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8. Makeba L.

Star Sitter
WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
3.3 mi. away
Boarding, House Sitting, Doggy Day Care
from
$49
per night
5.0 out of 5 stars
21 reviews
16 repeat clients
Profile image

Our dog Joe had a great time with Makeba! We appreciate the photos each day and fast communication. It is clear Makeba loves animals and deeply care for their well being. Will hopefully be able to utilize her services again in the future.

Availability updated yesterday
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Denontae G.
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Sitter Profile Image: Denontae G.
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9. Denontae G.

Your Pet’s Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
0.7 mi. away
Boarding
from
$50
per night
2 reviews

I can’t recommend Denontae G. enough as a pet sitter and dog walker! Denontae is incredibly caring, reliable, and attentive to every pet’s needs. He has a natural connection with animals, ensuring they feel safe, loved, and comfortable. I’ve seen firsthand how he goes above and beyond to provide personalized care, whether it’s keeping pets active with fun walks or ensuring their routines are followed perfectly. Pet parents can trust Denontae to treat their furry family members as his own, delivering outstanding service every time.

Availability updated 3 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Emily S.
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Sitter Profile Image: Emily S.
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10. Emily S.

Star Sitter
WFH Pup Lover
Near West Side, Chicago, IL, 60607
8.0 mi. away
Boarding, Doggy Day Care
from
$45
per night
5.0 out of 5 stars
15 reviews
3 repeat clients
Profile image

Emily watched my senior dog, Chloe for 4 days while I was out of town. Chloe is on a ton of meds and is a very anxious girl so I get nervous when I have to leave her. Emily was super communicative and sent lots of pics. She followed directions very well and Chloe seemed to really like her! I highly recommend booking Emily.

Availability updated yesterday
Sitter Profile Image: Tamara J.
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Sitter Profile Image: Tamara J.
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11. Tamara J.

Star Sitter
Experienced Dog Owner
Grand Boulevard, Chicago, IL, 60653
3.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$46
per night
5.0 out of 5 stars
9 reviews
4 repeat clients
Profile image

Tamara was amazing and graciously sent pics of my puppy when requested. He was happy and well taken care of. She was excellent when the date I entered was incorrect but still agreed to keep my fur baby once it was corrected. I highly recommend Tamara for pet sitting services.

Availability updated yesterday
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Katherine D.
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Sitter Profile Image: Katherine D.
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12. Katherine D.

Best friends deserves best care
OAK LAWN, IL, 60453
7.4 mi. away
Boarding, Doggy Day Care
from
$40
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
Profile image

Katherine was wonderful. I had no worries at all. She sent daily updates as well as pictures. A very loving and caring person. You won't regret booking your dogs stay with her.

Availability updated 22 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Kamiah & Casius D.
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Sitter Profile Image: Kamiah & Casius D.
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13. Kamiah & Casius D.

Pawsitevely Great Pup Care
Woodlawn, Chicago, IL, 60637
1.4 mi. away
Boarding, Dog Walking
from
$30
per night
5.0 out of 5 stars
6 reviews
1 repeat client
Profile image

kamiah and cassius were wonderful and i highly recommend them. they took great care of my dog. quick communicators, very professional, and they were kind when i was running late. i am looking forward to booking with them again!

Availability updated 68 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Tashea’ & Dushan M.
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Sitter Profile Image: Tashea’ & Dushan M.
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14. Tashea’ & Dushan M.

14+ years of dog care and love!
Auburn Gresham, Chicago, IL, 60620
2.5 mi. away
Boarding, Dog Walking
from
$50
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
Profile image

Tashea and Dushan did an amazing job watching my 2 month old American Bully. I was nervous because it was my first time away from her, but they kept me updated with pictures and videos and she looked super happy in every single one. I highly recommend them for dog boarding.

Availability updated 70 days ago
Sitter Profile Image: Holly R.
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Sitter Profile Image: Holly R.
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15. Holly R.

Your Pet's Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
0.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$50
per night
5.0 out of 5 stars
95 reviews
39 repeat clients
Profile image

Holly did an awesome job watching Layla for the weekend! We got lots of pictures and it looked like Layla and Holly’s dog Parker had a great time playing in the backyard. Layla came home very happy!

Availability updated 2 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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16. MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
2.3 mi. away
Boarding, Doggy Day Care
from
$40
per night
5.0 out of 5 stars
28 reviews
7 repeat clients
Profile image

Maria did a very good job taking care of Bubba while I was out of town. I would recommend Maria she not only cares for your pet, but also shows compassion towards their individual needs.

Availability updated 9 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Candace C.
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Sitter Profile Image: Candace C.
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17. Candace C.

Star Sitter
We treat your dog like it our own!
Blue Island, IL, 60406
7.8 mi. away
Boarding
from
$45
per night
5.0 out of 5 stars
70 reviews
31 repeat clients
Profile image

Candace is very good to my dogs during their stay. She asked some questions that she needed to know more about my dogs. I'm happy that my girls slept with her during the night, just like in my house. I'll definitely book with her again whenever I need her.

Availability updated today
Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
Verified Enhanced Background Check

18. Ashley M.

Rover 101
Star Sitter
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
6.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$53
per night
5.0 out of 5 stars
86 reviews
27 repeat clients
Profile image

My pup always loves the time he spends at Ashley’s! She is communicative and sends great photos and updates every day. Most importantly, she takes great care of my fur baby while I’m away!

Availability updated today
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Lisette S.
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Sitter Profile Image: Lisette S.
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19. Lisette S.

Star Sitter
For the love of pets!
McKinley Park, Chicago, IL, 60609
5.3 mi. away
Boarding, Doggy Day Care, Dog Walking
from
$30
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
Profile image

Lissete did a wonderful job. Luna will definitely see her soon!

Availability updated 29 days ago
Confirmed availability for Presidents' Day Weekend
Sitter Profile Image: Daniela M.
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Sitter Profile Image: Daniela M.
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20. Daniela M.

Different country, same love 🐾🐾
Avalon Park, Chicago, IL, 60619
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$38
per night
5.0 out of 5 stars
9 reviews
1 repeat client
Profile image

Amazing experience with Daniela! She kept us updated on a daily basis with pictures and videos of our dog while we were away and upon picking him up could tell he had been loved and cared for extremely well. Definitely going to be checking Daniela’s schedule next time we go out of town!

Availability updated 6 days ago
Confirmed availability for Presidents' Day Weekend

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