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

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1. Crystal R.

My home is where your pet is.
Chicago, IL, 60653
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
95 reviews
40 repeat clients
from
$21
per visit

Crystal was amazing! She was super communicative, punctual, loving and dedicated to taking care of our kitties while we were out of town. My kitties were a little disagreeable since it wasn’t us at home but she took such good care of them including administering medication to a somewhat grumpy furbaby. I was at ease knowing that she was taking care of them. I’m so appreciative of all she did!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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2. Coretta S.

Loves to accommodate furry friends
South Shore, Chicago, IL, 60649
4.3 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
57 reviews
21 repeat clients
from
$17
per visit

Coretta is amazing! She showed so much attention and care to our pets. I’m so grateful to have found her on Rover. She asked great questions and was very kind and accommodating. Highly recommend!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Michael D.
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Sitter Profile Image: Michael D.
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3. Michael D.

Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
3.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
8 repeat clients
from
$20
per visit

Michael was easy to work with and it really seems like he enjoys spending time with animals. Any pet would be in good hands with him. Will definitely be in touch with him again!

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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4. Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
114 reviews
36 repeat clients
from
$20
per visit

Emily was fantastic! She took lots of time to play with my two cats and provided me with thorough updates on how they were doing each day. She was also very responsive and communicative. I would definitely book her again!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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5. Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
16 repeat clients
from
$20
per visit

KT was the best with our two kitties! They gave great photo/video updates and communicated with me about any questions/issues that arose. They had a calm presence and the cats seemed to like them immediately. Will definitely book KT again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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6. Ashleigh H.

Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
3.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$17
per visit

Ashleigh is the perfect sitter. She's responsive and reliable. My dog is shy and she's able to build his trust. I am so happy to have her as my sitter 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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7. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$23
per visit

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

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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8. David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
79 reviews
32 repeat clients
from
$25
per visit

David was absolutely wonderful. Went above and beyond any rover sitter we have worked with, who were also great! He was incredibly kind and considerate with our pet and with our home. We highly highly recommend David for any of your pet’s needs!

Sitter Profile Image: Addy T.
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Sitter Profile Image: Addy T.
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9. Addy T.

Experienced with cats and dogs!
Chicago, IL, 60616
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$15
per visit

Addy was awesome!!! Thank you so much!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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10. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
from
$18
per visit

I highly recommend Chijioke for pet sitting. They are so reliable and caring!! I have booked them multiple times to pet sit for me while I've been out of town and they do a fantastic job every time! They cleaned the litter, fed and kept my cat company. Chijioke is a great communicator, they are thorough and easy to talk to! Plus they kept me updated throughout! A superstar pet sitter! Highly recommend 10/10!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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11. Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60616
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
86 repeat clients
from
$30
per visit

As usual, she is amazing. She’s a reliable sitter who we know we can turn to. Most recently she helped clean up a bad potty mess inside a kennel during one of her visits. We’re grateful and love knowing we can trust her :)

Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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12. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$22
per visit

Sujae is an excellent cat sitter. She came for drop in visits on time and consistently over multiple days. I liked seeing pictures of all the cats and the nice notes she left. She helped me out of a jam when another sitter cancelled my pet sitting while I was already out of town. Rover helped me find Sujae and I’m super happy we found each other! Sujae did a wonderful job for me and my cats. Thanks Sujae!

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Sitter Profile Image: Dominique C.
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Sitter Profile Image: Dominique C.
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13. Dominique C.

Lifelong Dog Lover and Caregiver!
Woodlawn, Chicago, IL, 60637
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$20
per visit

Dominique is excellent with Lily. She is patient, kind, and playful with her. She really goes the extra mile when working with my Lily. She is always on time and reliable. I highly recommend Dominique.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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14. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$16
per visit

Jabari is currently a co-owner of a 8-12 month old Yorkshire Terrier mix currently alongside me whom he frequently feeds, grooms and bonds with on a daily basis. Jabari has experience with both large and small breeds of dogs, he has worked with 1+ year old male Pure breed Cane Corso and 1+ year old female German Shepherd Mix who he has cared for and watched over several times over their life. As well as, already pet-sitting a variety of dogs for many owners within his own family. I would highly recommend Jabari for care for other's pets as he is responsible, caring and diligent about the well-being of all pets and properly caring for them according to their breeds, sizes and ages.

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Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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15. Taylor L.

Loving Pet Sitter, Cats & Dogs
Kenwood, Chicago, IL, 60615
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$12
per visit

Taylor went above and beyond, she was super kind and understanding of our dogs needs. She provided lots of updates and we felt assured that our pets were in safe hands!

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Sitter Profile Image: Alma G.
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Sitter Profile Image: Alma G.
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16. Alma G.

Caring, loving and responsible!
Chicago, IL, 60615
1.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$17
per visit

About: My friends, family and neighbors have all counted on me to look after their pets since I was 15 years old. I grew up volunteering in dog shelters and caring for my own pet growing up. I treat all pets as if they were my own! I work full time at a fitness center, but my hours are flexible and I have Fridays and Saturdays off. I typically work later in the mornings and get off in the evenings, but I am able to adjust hours accordingly. I have a cozy apartment with a huge park and dog park 3 minutes away. I make my space work for them and really spend time with them outside and playing as much as they need. My neighborhood is great for those much needed walks!

Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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17. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$17
per visit

Abi was the best! She is so caring and went above and beyond. When I asked her to check in with me a couple times while I was gone (8 days) she certainly did, and even sent photos which gave me peace of mind! I came home to very happy cats! I cannot recommend her enough. Thank you Abi!!

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Sitter Profile Image: Max C.
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Sitter Profile Image: Max C.
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18. Max C.

I am a dog lover who cares
Grand Boulevard, Chicago, IL, 60615
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
15 years of experience
from
$17
per visit

About: I have been a dog and lover and pet owner for years and have the patience and time to care for any pet that is manageable I own my own business and have a flexible schedule that can cater to any needs and wants that are needed for both of us to be happy I have a fenced yard and have a single family home with a basement if the pet needs a more private attention and care needed

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Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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19. Madeleine G.

Dog lover/babysitter for your pup!
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
10 repeat clients
from
$16
per visit

Madeleine was great with our dog and was flexible enough to work with our changing schedules. Our dog is used to having someone around all day, so she greatly appreciated the time Madeleine spent with her.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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20. Jasmine P.

Rover 101
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
61 reviews
21 repeat clients
from
$30
per visit

Jasmine was wonderful! We had just adopted our new kitty Ollie and he badly needed his claws trimmed. We didn't want to traumatize him with a vet trip so soon after we'd brought him home, so we asked Jasmine if she could come and show us how to trim his nails at home since neither of us was familiar with the process. She went above and beyond both trimming his longest claws and giving us lots of helpful tips to help us succeed with the process ourselves. Highly recommend Jasmine to care for your feline friends!

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Grand Boulevard:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7915 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.

Drop-In Visits