Pet Sitting & Drop Ins In Grand Boulevard

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

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Top rated Grand Boulevard pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
82 reviews
33 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Qutress was great with our shy cat, who even let Qutress pet her which is quite rare for newcomers! She was very communicative and gave us wonderful updates every day. Highly recommend!

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Luke M.
Sitter Profile Image: Amiyah W.
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Amiyah W.
from
$15
per visit
3 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

About: I've had pets since I was 9. From 9 till now I've had cats, dogs, fishes, and guinea pigs. I have experience with dealing with pets that may have previously trauma issues also with pets that may need careful care like medince or special needs. Even pets that don't need extra care just pets that wants to have long walks or need a lot of play time . I am currently in school. So I will be working part time for Rover. Evening and nights works best for the weekdays and for the weekends I am open for anytime you need. For cats do have multiple cat bags if they need to brought to a appointment or any where else. And foot dogs if you don't have a leach I can get one but I would prefer for you to have leeches and rates of pets need to be taken out of the house .

Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was very punctual, provided lots of updates and pictures, communicated well, and poppy loved her! We will definitely be using her again and I 10/10 recommend her!

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Freddie V.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
248 reviews
86 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

It was my first time using rover and I was looking for someone who truly understands dogs, and its Tamara! Tamara was a true blessing while I was away in Mexico. My dog isn’t usually quick to trust—he even tried to bite her when they first met—but she was so patient and kind with him. By the end of the week, he was waiting at the door for her, tail wagging, 30 minutes early. I could tell he really bonded with her. I’m so grateful and would absolutely have her watch him again.

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Al T.
Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
43 reviews
15 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Very prompt, communicative, and went above and beyond! Highly recommend to anyone!

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Sreyas M.
Sitter Profile Image: Daphnay S.
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Daphnay S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
24 reviews
10 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.

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Petia O.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per visit
4.7 out of 5 stars
12 reviews
6 repeat clients
10 years of experience
Chicago, IL, 60653

Jasmine R was awesome. Thorough and punctual. My kitty was happy and my home was just as I left it. I will use her services again.

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Stacey S.
Sitter Profile Image: Simone B.
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Simone B.
from
$25
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
23 years of experience
Chicago, IL, 60615

Simone is absolutely amazing! She did a drop in before our first visit, which we know is extra work and she didn’t mind at all to take care of our sweet puppy who’s 4 months old. She didn’t mind the zoomies and I’m sure was so patient and playful with our pup we are absolutely booking a drop in again!

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Dana W.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

Cassandra listens and is trustworthy. We spoke for awhile exchanging dog (pet watching) experiences and I knew I could trust her with my dogs and my home: Her visit consisted of having lockbox access to our house, access to the dogs and returning everything as requested.

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Heather B.
Sitter Profile Image: Cassandra H.
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Cassandra H.
from
$15
per visit
5.0 out of 5 stars
69 reviews
25 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.

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Sud R.
Sitter Profile Image: Taylor W.
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Taylor W.
from
$20
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
17 years of experience
Chicago, IL, 60615

Great! No complaints. Will be scheduling again soon. My cats loved her and she followed instructions exactly.

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Chevonne C.
Sitter Profile Image: Jasmine P.
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Jasmine P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
97 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

I booked Jasmine VERY last minute and she got back to me quickly and was available for a meet and greet the same day. Everything went off without a hitch while I was gone. Highly recommend.

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Wesley M.
Sitter Profile Image: Ruari H.
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Ruari H.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Bridgeport, Chicago, IL, 60616

Great communication and was very helpful in a time of need.

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Che R.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$30
per visit
5.0 out of 5 stars
30 reviews
8 repeat clients
20 years of experience
Douglas, Chicago, IL, 60609

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

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Lillian & Jason A.
Sitter Profile Image: Brianna B.
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Brianna B.
from
$10
per visit
5.0 out of 5 stars
6 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

Brianna was super communicative, timely, and cared well for my cat while giving detailed updates! Would book again!

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Ria M.
Sitter Profile Image: Christina D.
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Christina D.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
6 reviews
3 repeat clients
13 years of experience
Oakland, Chicago, IL, 60653

Christina did a great job taking care of my five cats, two of whom zi have medical needs. I really appreciated her daily updates and photos of my boys.

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Susan B.
Sitter Profile Image: Jessy M.
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Jessy M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
13 years of experience
Hyde Park, Chicago, IL, 60615

Jessy was very responsive and did everything I asked of her!

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Leah C.
Sitter Profile Image: Mia L.
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Mia L.
from
$20
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
7 years of experience
Hyde Park, Chicago, IL, 60615

This is my second booking with Mia. I received daily updates over the two weeks I was away and once again returned home to a happy, healthy cat.

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Teresa R.
Sitter Profile Image: Veronica M.
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Veronica M.
from
$16
per visit
4 years of experience
Chicago, IL, 60653

About: I love taking care of pets (mostly cats)! I will make sure your pet has been walked (for dogs) playtime, a clean litter box (for cats), and the proper food to make sure they're healthy. I'm currently working full time, but I have plenty of time in the evenings for your pet! I'm available after 5pm during the week and after 12pm on Saturdays. For in-home services, I make sure to follow all the directions the owner gives me. I also will clean up and alert the owner if their pet has an accident or throws up in their home.

Sitter Profile Image: Ava M.
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Ava M.
from
$20
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
11 years of experience
Hyde Park, Chicago, IL, 60637

Ava went above and beyond watching my 3-year old golden. She clearly loves dogs and loves her job. Would be happy to book with again.

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Jada D.
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Grand Boulevard pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ruari was very responsive and sent photos to make certain to me that everything was good for our pet. Would recommend to anyone

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Will B.
Drop-In Visits
5.0 out of 5 stars

Christina did a great job taking care of my five cats, two of whom zi have medical needs. I really appreciated her daily updates and photos of my boys.

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Susan B.
Drop-In Visits
5.0 out of 5 stars

Brianna was super communicative, timely, and cared well for my cat while giving detailed updates! Would book again!

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Ria M.
Drop-In Visits
5.0 out of 5 stars

Maya took great care of both my indoor and outdoor cats while I was away. She was in regular communication with me about whether or not the cats were visible during her drop-ins, as well as how open they were to getting some rubs and TLC. She even brought my dumpsters back into my yard on trash day and made sure packages delivered to my home made it safely inside. Maya is a sweetheart and I absolutely plan on having her care for my babies for my next extended out of town trip!

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Erica M.
Drop-In Visits
5.0 out of 5 stars

My cat absolutely loved Ashley! She came on schedule and I enjoyed looking at the drop-in report cards. I feel confident in booking her again.

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Luis C.
Drop-In Visits
5.0 out of 5 stars

Evan did a wonderful job watching our cat for a long weekend. He was communicative and responsive, which made us feel comfortable and confident that our cat was in great hands.

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Anna B.
Drop-In Visits
5.0 out of 5 stars

Daphnay was awesome with Zena. She followed all of our instructions for Drop-in visits, sent reports and updates after each visit. We'd definitely book with her again. Thanks so much again, Daphnay!

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Chent & Princess S.
Drop-In Visits
5.0 out of 5 stars

Called before to establish clear, detailed communication for her checklist. Walked my dog and sent update videos/pictures as she completed her checklist throughout the service.

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Jonte' W.
Drop-In Visits
5.0 out of 5 stars

Bri was responsive and super friendly with our kitty crew! She accommodated us on short notice thankfully and though our cats were hot and cold with her (typical of felines) she was patient and calm with them. Would definitely book again!

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Merl K.
Drop-In Visits
5.0 out of 5 stars

Marisa watched my two cats over Memorial Day weekend- she did an amazing job sending photos and videos and following care instructions. I would recommend her to anyone looking for a reliable sitter!

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Kaleigh H.
Drop-In Visits
5.0 out of 5 stars

Rachel was great! We loved having her take care of the girls again and would 1000% book with her again!

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Payton D.
Drop-In Visits
5.0 out of 5 stars

Joselin was so kind and responsive. He took care of my sweet baby cat for two days very well. She is so communicative! She sent a lot of photos and videos of my cat. Highly recommended.

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Nargess H.
Drop-In Visits
5.0 out of 5 stars

Ericka is fantastic! I had peace of mind while I was away knowing she was taking care of my shy cat.

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Maria C.
Drop-In Visits
5.0 out of 5 stars

Our three cats are all fluffy and happy when we get back from trips, and that’s all we can ask for :) we feel very lucky to have found someone like Jason to care for our babies — he is the best!

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Gracin P.
Drop-In Visits
5.0 out of 5 stars

Nikki was so great!! Spent a good amount of time with my cats and they seemed so happy when I got back.

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Katie D.
Drop-In Visits
5.0 out of 5 stars

Thank you so much for caring for my babies! I appreciate it! highly recommend for all your pet booking needs!

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Johanna B.
Drop-In Visits
5.0 out of 5 stars

Kaylie is super friendly and sweet! She communicated with me on all visits and sent pictures of my Clyde!

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Jennifer H.
Drop-In Visits
5.0 out of 5 stars

Lucille is definitely a kind soul and I appreciate her help walking my best friend. I would highly recommend and book again ☺️

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Alison L.
Drop-In Visits
5.0 out of 5 stars

Katherine did a great job as always! Very responsive, sent updates and pictures, and went above and beyond to help with our cats!

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Andrew T.
Drop-In Visits
5.0 out of 5 stars

Thank you for taking care of Kaia. It seemed like our dog had a great time with her doing a brief walk and some cuddle time. We definitely recommend Annie and looks forward to using her services again.

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NORMA L.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Grand Boulevard pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Grand Boulevard.

Rover makes it easy to find Grand Boulevard pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.