Pet Sitting & Drop Ins in Grand Boulevard, Chicago

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check
1.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
57 reviews
30 repeat clients
from
$21
per visit

Crystal took wonderful care of my shy senior cat and even got her to open up to play! Crystal clearly knew what she was doing from the get go and she was diligent, reliable, and trustworthy. She was also very responsive to all my messages and kept me regularly updated. She's a great sitter!

Calendar Recently Updated
Sitter Profile Image: Josie S.
Verified Enhanced Background Check
Sitter Profile Image: Josie S.
Verified Enhanced Background Check
2.

Josie S.

Animal Whispering Weirdo
Chicago, IL, 60608
Drop-In Visits
5.0
9 reviews
1 repeat client
from
$20
per visit

Josie was a great sitter and very knowledgeable about cat care. She is considerate, communicative, and punctual; exactly what we want in a pet sitter.

Calendar Recently Updated
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
3.

Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
47 reviews
14 repeat clients
from
$20
per visit

Katherine is wonderful! We have a new kitten and an older fella cat, we had to leave town for a week, and weren't sure how the kitten would respond to his first time with us being away, how many things would be broken, and who could be a good fit to keep an eye on things and make sure the boys were well cared for. Katherine is an excellent communicator, provides tons of great information during visits, and gave us peace of mind that our home and kitties were in good hands. If Katherine is available, you'll be lucky to have them!

Calendar Recently Updated
Sitter Profile Image: David K.
Verified Enhanced Background Check
Sitter Profile Image: David K.
Verified Enhanced Background Check
4.

David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
68 reviews
29 repeat clients
from
$20
per visit

David very clearly LOVES animals. He spent the time to make sure our cats were well loved and cared for and even went out of his way (literally) to make it out to our place over the holiday weekend. I would recommend David for any services you may need!

Calendar Recently Updated
Sitter Profile Image: Lauren W.
Verified Enhanced Background Check
Sitter Profile Image: Lauren W.
Verified Enhanced Background Check
5.

Lauren W.

Home part-time- and I love dogs!
Chicago, IL, 60621
Drop-In Visits, Doggy Day Care, Dog Walking
3 reviews
from
$18
per visit

I’ve known Lauren for many years. She is always a reliable dog sitter for me when I go out of town. My fur baby loves Lauren’s compassionate and energetic personality. I can also count on her to follow his eating and walking routines for his comfort. I would highly recommend her!

Calendar Recently Updated
Sitter Profile Image: Michelle B.
Verified Enhanced Background Check
Sitter Profile Image: Michelle B.
Verified Enhanced Background Check
6.

Michelle B.

Active Walker and Loving Pet Sitter
Chicago, IL, 60616
Drop-In Visits, Dog Walking
5.0
3 reviews
1 repeat client
from
$25
per visit

Perfect! Thank you!!!

Calendar Recently Updated
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
7.

Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking
5.0
20 reviews
5 repeat clients
from
$23
per visit

Levi took excellent care of my pups! She's extremely knowledgeable about pet care and very communicative! I'll definitely be utilizing her services again in the near future!

Calendar Recently Updated
Sitter Profile Image: Michael P.
Verified Enhanced Background Check
Sitter Profile Image: Michael P.
Verified Enhanced Background Check
8.

Michael P.

Diabetus Puurficient Cat Dad
Chicago, IL, 60653
House Sitting, Drop-In Visits
7 reviews
from
$33
per visit

Michael is EXCELLENT with pets and has taken care of my beagle Sophia and Mini Pin Lolita many times over the past two years. Both my girls love him and are very happy to see him when they stay with him or he walks them. Michael truly is a dog and cat whisperer and all the pets in my neighborhood also love him. His gentle nature and love of animals shows in every interaction! Michael is incredibly responsible, trustworthy, and dependable when called upon to care for my pets, and I would highly recommend him to anyone needing pet care!

Calendar Recently Updated
Sitter Profile Image: Emily N.
Verified Background Check
Sitter Profile Image: Emily N.
Verified Background Check
9.

Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
90 reviews
27 repeat clients
from
$20
per visit

Callie is so comfortable with Emily! She truly is so kind and detail oriented when it comes to Callie’s care. I appreciate that she goes the extra mile to make sure our cat feels comfortable and safe while we are away. She is also great in communication and will help out wherever she can.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: jessica f.
Verified Enhanced Background Check
Sitter Profile Image: jessica f.
Verified Enhanced Background Check
10.

jessica f.

Everything on earth has a purpose
Chicago, IL, 60616
Drop-In Visits, Dog Walking
2 reviews
from
$25
per visit

A friend of mine recommended Jessica, best day ever when I hired her to walk my 2 crazy , excitable , loud terriers. My girls don't like strangers, but they took to Jessica right away . She is so good with them . She always has a treat for them . When she comes thru the door , they run and get their toys , it's playtime ! Jessica is the best and I trust her completely with my baby girls .

Sitter Profile Image: John M.
Verified Enhanced Background Check
Sitter Profile Image: John M.
Verified Enhanced Background Check
11.

John M.

UChicago student; animal lover
Hyde Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$20
per visit

John is excellent with both cats and dogs. He is incredibly patient and gentle with my cats who I have left in his care several times. John is also a big dog-lover and has cared for his three dogs for many years. John is reliable and dependable and will take excellent care of your pets!

Calendar Recently Updated
Sitter Profile Image: Mikayla V.
Verified Background Check
Sitter Profile Image: Mikayla V.
Verified Background Check
12.

Mikayla V.

Fur Baby Aficionado!
Chicago, IL, 60637
House Sitting, Drop-In Visits
5.0
23 reviews
9 repeat clients
from
$30
per visit

Mikayla was super responsive and friendly while booking. I had never used Rover before, so she was extra helpful in in the process. She was willing to meet in person first and was flexible along the way. She even was able to pivot and help us keep track of a medical issue our cat was having prior to her visits with him.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Kayla S.
Verified Enhanced Background Check
Sitter Profile Image: Kayla S.
Verified Enhanced Background Check
13.

Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
26 reviews
13 repeat clients
from
$25
per visit

Kayla did a fine job taking care of my two cats. She was prompt and consistent following my directions. Taking photos and posting them was a surprise bonus. I'm fully satisfied with Kayla and will book her again when I need help.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Viola R.
Verified Enhanced Background Check
Sitter Profile Image: Viola R.
Verified Enhanced Background Check
14.

Viola R.

A dogs best friend
Grand Boulevard, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
7 reviews
3 repeat clients
from
$35
per visit

My dog loves Viola! She’s one of the very few people that he truly feels the most comfortable around, so she’s one I know I can depend on to dogsit for me whenever I travel and can’t take him with me, and I’ve never had ANY problems when I come to pick him up after. Viola is attentive, caring, and very responsible when it comes to administering his medications and feeding him according to his special diet. Of course I’d recommend her!

Sitter Profile Image: Toni B.
Verified Enhanced Background Check
Sitter Profile Image: Toni B.
Verified Enhanced Background Check
15.

Toni B.

There for your pet, there for you !
Chicago, IL, 60653
Drop-In Visits, Dog Walking
5.0
10 reviews
1 repeat client
from
$15
per visit

Amazing and caring sitter! Did exactly as instructed and left a detailed summary. Took lots of pictures and handled caring for a new type of pet (turtle) amazingly! Definitely recommend.

Calendar Recently Updated
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
16.

Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
15 reviews
4 repeat clients
from
$15
per visit

Taylor was very attentive to my dog because when he came home to me he was very happy and showed no evidence of mistreatment. She was able to take him on a small walk throughout the day and give him ample potty breaks. She was very nice and responsive with her messaging and I would definitely use her as a sitter again.

Sitter Profile Image: Robert L.
Verified Enhanced Background Check
Sitter Profile Image: Robert L.
Verified Enhanced Background Check
17.

Robert L.

Dog groomer, bather, walker
Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$17
per visit

Robert has watched my dog several times. He's always responsible with taking her out, going for walks and sending pictures. She always looks forward to his visits

Sitter Profile Image: Valeria V.
Verified Enhanced Background Check
Sitter Profile Image: Valeria V.
Verified Enhanced Background Check
18.

Valeria V.

Walk, play, cuddle and repeat!
Grand Boulevard, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
1 repeat client
from
$15
per visit

Thanks for taking care of my Blue!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Pamela K.
Verified Background Check
Sitter Profile Image: Pamela K.
Verified Background Check
19.

Pamela K.

Dogs are four legged best friends
Grand Boulevard, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
27 reviews
10 repeat clients
from
$70
per visit

Pamela is friendly, accommodating, and professional

Confirmed availability: Christmas and New Year's
Sitter Profile Image: E K.
Verified Background Check
Sitter Profile Image: E K.
Verified Background Check
20.

E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
233 reviews
101 repeat clients
from
$40
per visit

She was great! Took great care of our big, energetic dog. Would definitely book again

Search Map

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 owners have reviewed sitters in Grand Boulevard, 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.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Grand Boulevard pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Grand Boulevard, Chicago who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

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 Grand Boulevard, 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:

Drop-In Visits