Dog Boarding in Woodlawn, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Easter Weekend
Sitter Profile Image: Holly R.
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Sitter Profile Image: Holly R.
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1.

Holly R.

Your Pet's Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
0.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
70 reviews
34 repeat clients
from
$60
per night

Holly was amazing! Our dog absolutely loved her and her dog Parker. We appreciated how she made Pippi feel at home, and had great communication with us throughout our dog's stay. Her big fenced yard is incredible for dogs that like to run.

Confirmed availability: Easter Weekend
Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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2.

Makeba L.

WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
2.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
13 reviews
9 repeat clients
from
$45
per night

Makeba took wonderful care of my Mistee pooh. She was available for meet & greet and displayed a genuine warmth and affection toward my fur-baby. Mistee had a ball which was evident my the communication and pictures sent to keep us up to date. Thank you Makeba. We will be seeing you a again soon 🐶

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Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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3.

Ashley B.

Open house for Pets
Hyde Park, Chicago, IL, 60615
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
36 repeat clients
from
$57
per night

Our big boy Masai loved staying with Ashley and her beautiful family. They took great care of him. And gave of us photo updates which kept us from wondering about his first overnight stay with someone he'd just met. We will definitely be calling on them again... I can't recommend them enough!

Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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4.

Kyle H.

Rover 101
Over a decade of experience!
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$55
per night

Kyle and Ben were great! They sent an email update with a photo so we could see how it was going. They were also very responsive and flexible with the drop-off and pick-up time!

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Sitter Profile Image: Wade S.
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Sitter Profile Image: Wade S.
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5.

Wade S.

The Dog Whisperer 🐾
South Shore, Chicago, IL, 60649
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
from
$50
per night

Wade was a outstanding sitter to my baby cash he sent random pictures and videos throughout the day him and his wife took care of my baby with ease I highly recommend wade for your dog care needs and I’ll definitely be booking with him again

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Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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6.

Ebonee A.

12 + years of Vet-Tech experience!
Hyde Park, Chicago, IL, 60615
1.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
27 reviews
11 repeat clients
from
$50
per night

My puppy (Beau) had an amazing time with Ebonee. She was very communicative and sent pictures/videos daily. He seemed to be really calm and happy during his stay with Ebonee. ?

Confirmed availability: Easter Weekend
Sitter Profile Image: Mayela E.
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Sitter Profile Image: Mayela E.
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7.

Mayela E.

I’d like to be a dog in other lives
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$40
per night

Mayela was such a wonderful sitter for Milo. She provided so many updates and pictures every single day. She asked questions to make sure Milo would be happy and well taken care of. I will definitely be using Mayela again and recommend her to everyone.

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Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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8.

Courtney B.

Your Dog's Favorite Sitter
Grand Boulevard, CHICAGO, IL, 60653
2.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$39
per night

Courtney has been consistently prompt in her communications and treated my Billie so well during her stay! Knowing that she had a playmate and was being kept in good care was a relief for me while I was out of town :)

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Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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9.

Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
2.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
14 repeat clients
from
$55
per night

I chose Kayla to take care of my two dogs over Christmas and she did a wonderful job. I left town and she would send daily updates with lots of pictures of my dogs. I was initially concerned of leaving my dogs with someone else, as this was my first time using Rover, but Im super satisfied with the care Kayla provided. She is also super quick to respond to messages, which made me feel even more comfortable. I also appreciated the opportunity to visit her before actually dropping my dogs. Her mom was also super sweet and it seems my dogs always had someone with them. 10/10

Sitter Profile Image: Tashea’ & Dushan M.
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Sitter Profile Image: Tashea’ & Dushan M.
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10.

Tashea’ & Dushan M.

14 years of dog care and love!
Auburn Gresham, Chicago, IL, 60620
4.0 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

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.

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Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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11.

Ashley M.

Rover 101
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
6.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
36 reviews
15 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: Easter Weekend
Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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12.

Tania B.

Rover 101
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
5.7 mi. away
Boarding
5.0 out of 5 stars
32 reviews
9 repeat clients
from
$45
per night

Tania is amazing! She takes such good care of our dog who is a little older and very nervous. He genuinely seems comfortable with her which says a lot. She sends lots of pictures and updates so I know he is happy and safe while we are away. I highly recommend her!

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Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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13.

MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
1.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
10 reviews
1 repeat client
from
$40
per night

Maria/MJ was great. She was very communicative from the initial request to board through when I picked up my dog. She sent updates and pictures while I was away and asked questions to ensure she was providing my pup with the highest quality of care. I highly recommend her based on my visit.

Sitter Profile Image: Ra'eesa S.
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Sitter Profile Image: Ra'eesa S.
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14.

Ra'eesa S.

Extraordinary pet care! :)
Woodlawn, Chicago, IL, 60637
0.2 mi. away
Boarding
5.0 out of 5 stars
18 reviews
6 repeat clients
from
$45
per night

Ra’eesa was an amazing sitter for our pup. She was attentive and sent pictures and updates while we were gone. Thank you Ra’eesa for taking good care of Clue while we were away!

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Sitter Profile Image: Xue G.
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Sitter Profile Image: Xue G.
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15.

Xue G.

Pawsitively Reliable Pet Sitter!
Near South Side, Chicago, IL, 60605
6.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$40
per night

Xue was amazing in watching our dog Freddy! She was very attentive, responsive and provided the best care! Everyday we would get an update which puts us at ease while away. I would highly, highly recommend her!

Sitter Profile Image: Tonisa J.
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Sitter Profile Image: Tonisa J.
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16.

Tonisa J.

Rover 101
Your pups second home....
Calumet Heights, chicago, IL, 60617
3.1 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
68 reviews
30 repeat clients
from
$55
per night

Tonisa was an excellent dog sitter. She took us at the last hour because our other dog sitter had an emergency. Tonisa provided us with pics and updates throughout the visit. I highly recommend her and our dogs will definitely be back.

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Sitter Profile Image: Dwight C.
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Sitter Profile Image: Dwight C.
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17.

Dwight C.

Rover 101
Work from home - large fenced yard
Woodlawn, Chicago, IL, 60637
0.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
151 reviews
65 repeat clients
from
$30
per night

Angel loved Dwight the minute he saw him. He gave us daily updates on Angel and did an excellent job watching him! Will definitely book Dwight whenever we're in Chicago

Confirmed availability: Easter Weekend
Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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18.

Viola R.

A dogs best friend
Grand Boulevard, Chicago, IL, 60615
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$30
per night

Viola did a fantastic job on taking care of my Zoë. She sent updates and pictures of everything that she had been doing for Zoë. I saw how comfortable she made Zoë feel being in her care. I will definitely have Viola to take care of Zoë again whenever Viola is available.

Confirmed availability: Easter Weekend
Sitter Profile Image: Sateela H.
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Sitter Profile Image: Sateela H.
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19.

Sateela H.

Passionate Pet Enthusiast
Auburn Gresham, Chicago, IL, 60620
3.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
4 reviews
from
$50
per night

Sateela participated in assisting on getting a lost dog back to her rightful owner and caring for the dog verses having the dog go to an overcrowded shelter. This act of kindness is not to go unnoticed.

Sitter Profile Image: Chaeyeong J.
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Sitter Profile Image: Chaeyeong J.
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20.

Chaeyeong J.

Reliable Rover for ur furry friends
Kenwood, Chicago, IL, 60615
1.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$60
per night

Chae is amazing! She took such good care of our puppy Millie, and eased all of my concerns with it being our first time with Rover. We know Millie loved staying with Chae, and would definitely book again! 🩷🩷🩷

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Rover also offers Dog Boarding in these neighborhoods:

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Dog lovers in Woodlawn, Chicago, IL love dog sitters on Rover.com. Over 7915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Woodlawn dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Woodlawn, Chicago, IL, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Woodlawn, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including:

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