Pet Sitting & Drop Ins in Woodlawn, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Susan C.
1.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan is the best. She regularly kept us updated and sent photos. She gave us a thorough out brief as to what, if anything is going on with my fur babies. I loo… (more)

from
$50
per night
Confirmed availability: Memorial Day
Nakeisha B.
Your fur baby will be in good handsGrand Crossing, Chicago, IL, 60619
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Nakeisha took great care of Bella while I was away for the weekend. She sent updates throughout the day that consisted of photos and videos. She also took great… (more)

from
$50
per night
Calendar Recently Updated
Katja G.
3.
Over 10 years of dog experience!Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Wow, this was the best experience. You treated my baby (Dolly Parton) with the best care and made me feel so comfortable that she was safe and in the best hands… (more)

from
$35
per night
Calendar Recently Updated
Steve & Monica K.
Dog people are good peopleKenwood, Chicago, IL, 60653
Dog Boarding

Steve and Monica took great care of my dog! They were both very friendly and approachable, clearly loved having animals in the home. Their two small children, c… (more)

from
$40
per night
Calendar Recently Updated
David N.
5.
NOT JUST A PET BUT FAMILYLower West Side, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

Very responsive and flexible with drop off and pick up! David was understanding of my dog’s hesitation and eased him into the group setting. Will definitely boo… (more)

from
$40
per night
Calendar Recently Updated
Attentive & Loving Walker HereWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

My relationship with Antonio, has grown into a friendship. He played a major role in helping my extremely shy bulldog, become more outgoing; and interactive wit… (more)

from
$40
per night
Calendar Recently Updated
7.
Work from home - large fenced yardWoodlawn, Chicago, IL, 60637
Dog Boarding, Doggy Day Care

When reading Dwight's reviews someone said, "Don't consider anyone else, book him now!" Again, I repeat...Don't consider anyone else, book him now! Never have I… (more)

from
$30
per night
Confirmed availability: Memorial Day
Your pups new favorite Auntie!Near South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

Marjani is the best! Henry has a lot of anxiety, especially new people and Marjani was patient and made him feel right at home. Henry had so much fun staying wi… (more)

from
$60
per night
Calendar Recently Updated
Yoga Sitter / Loving+Gentle+SereneWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking
10 years of experience

About: What do you do when you need a gentle + loving sitter, who's caring, a great communicator and loves to do animal yoga then snuggle?  You call me!  Hi… (more)

from
$50
per night
Calendar Recently Updated
10.
Your pups second home....Calumet Heights, chicago, IL, 60617
Dog Boarding, Drop-In Visits

6/5 stars if we could! We came over to Tonisa’s after booking a very last-minute stay, and our goldendoodle girls were SO excited to see her! It’s obvious they … (more)

from
$35
per night
Confirmed availability: Memorial Day
11.
Woman boss and a bark of a hustleHyde Park, Chicago, IL, 60615
Dog Boarding, Doggy Day Care

Ashley is very professional, gives great updates about your pup, and takes the job of caring for your pet seriously! 10/10, would strongly recommend. (more)

from
$45
per night
Confirmed availability: Memorial Day
Animal lover!park nearby/work at🏠Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Dog Walking

Kimberley was an amazing dog sitter! I would absolutely request her again! She made sure to update me several times a day with photos and videos of my dog along… (more)

from
$44
per night
Confirmed availability: Memorial Day
13.
Beloved dog whisperer, is me!South Shore, Chicago, IL, 60649
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jasmine P. is an attentive and kind caregiver. She provided my puppy personalized attention and paid special attention to soothe his anxiety over being in a un… (more)

from
$55
per night
Calendar Recently Updated
14.
Dog mom who has space to play!Chicago Lawn, Chicago, IL, 60629
Dog Boarding, House Sitting, Drop-In Visits

Alishia did great with my pup. My dog got along with her dog and looked like she had a good time over the weekend. When I picked her up she was happy and energe… (more)

from
$40
per night
Calendar Recently Updated
15.
This is a dream job for me!Bridgeport, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

Monica is a natural with dogs! My sweet little dachshund has some special needs (mostly blind and can be a little anxious about being away from home) but Monica… (more)

from
$35
per night
Calendar Recently Updated
16.
Plenty of long walks and treats!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Willis and I LOVE JASMINE!!!!! We started initially with a play-date and I had a really great feeling about jasmine and her watching my babe. Throughout my out … (more)

from
$40
per night
Confirmed availability: Memorial Day
17.
DOGGY FUNNew City, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ethel was great! My dog has separation anxiety so I’m sure it wasn’t easy that he cried at night. When we were leaving he cried when he noticed Ethel wasn’t co… (more)

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$45
per night
Calendar Recently Updated
18.
Work from home/flexible pet sitter!Near North Side, Chicago, IL, 60654
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Would highly recommend Brandon! He communicated well and sent frequent updates and pictures. He took such good care of my dog and we will definitely rebook! (more)

from
$55
per night
Confirmed availability: Memorial Day
19.
Work from home | Treats. Play. ♥️Loop, Chicago, IL, 60607
Dog Boarding

Alison took such great care of Wallie, even taking him to the dog beach. He was very sad to leave her. So appreciated her going above and beyond. (more)

from
$80
per night
Calendar Recently Updated
20.
Dogs are my favorite people!Near West Side, CHICAGO, IL, 60608
Dog Boarding

Jackie took care of our Maltese, Lychee, whenever I had to travel for work or for a family vacation. Jackie is detail-oriented and sends regular updates with pi… (more)

from
$35
per night

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Woodlawn, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Rover.com is the simple, savvy way to find and book Woodlawn, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Woodlawn, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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: