Pet Sitting & Drop Ins in Oakland, 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: Easter 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
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
85 reviews
36 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!

Confirmed availability: Easter Weekend
Sitter Profile Image: Katie C.
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Sitter Profile Image: Katie C.
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2. Katie C.

Let me care for your fur-babies 🥰
Near South Side, Chicago, IL, 60605
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
3 repeat clients
from
$17
per visit

Katie is an excellent pet-care provider. She has had so many experiences working with a variety of animals. She has had experience working with farm animals to also working with senior-dogs. She has done an excellent job caring for pets of all types and all energies and I would highly recommend her for all your pet related services!

Confirmed availability: Easter Weekend
Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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3. Dalila E.

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

Dalila was great with my cat Shelby! She went out of her way to make my cat (who is afraid of strangers) feel at ease, and she even warmed up to her sooner than I expected. I’d definitely hire her again!

Confirmed availability: Easter Weekend
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
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
111 reviews
34 repeat clients
from
$20
per visit

Emliy was Awesome! She did such a great job taking care of our 3 cats! We got updates with pictures everyday while we were gone. She took the time to learn each cats personalities and treated the with so much care! I would highly recommend her to anyone that needs someone to look after their pets.

Confirmed availability: Easter Weekend
Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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5. David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
31 repeat clients
from
$20
per visit

David was so patient and understanding with my dog, Frankie! He was always on time, willing with work with Frankie’s needs and did an amazing job. I can’t recommend him enough!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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6. Katherine B.

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

Katherine was great! Came in clutch for a last minute cat sitting request and provided really detailed updates and lots of photos/videos while I was away. I came home to a happy kitty and watered plants.

Confirmed availability: Easter Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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7. Jasmine P.

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

Jasmine was amazing, especially on short notice. Thorough, communicative, and proactive. My favorite is when she left the light on because she knew it would be dark soon and wanted to provide some comfort. It was everyone you’d want in someone caring for your pup. Will definitely use her again.

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Sitter Profile Image: Nycol H.
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Sitter Profile Image: Nycol H.
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8. Nycol H.

Hi, I’m Nycol!
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits
from
$25
per visit

Nycol is incredibly responsible and caring towards both animals and humans! Nycol has watched over our dear Sadie and Bernie for the last 2 years and she is still the only one we trust to watch them! I’m immensely grateful for Nycol and the bond she shares with our loving fur babies.

Sitter Profile Image: Sophia E.
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Sitter Profile Image: Sophia E.
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9. Sophia E.

A pet sitter with a big heart!
Chicago, IL, 60609
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
1 repeat client
from
$31
per visit

Sophia was absolutely amazing and took great care of Nani and Ohana! We’re definitely booking with her again!

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Sitter Profile Image: Olivia A.
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Sitter Profile Image: Olivia A.
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10. Olivia A.

Flexible and reliable pet sitter!
Chicago, IL, 60615
1.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$17
per visit

Olivia did a great job checking in on both my cat and my dog. Both the cat and the dog are shy and usually take a while to warm up to new people, but they both seemed to love Olivia. She was also very communicative and sent a great pic of my guys. Highly recommend, ill definitely be rebooking next time I need a drop in.

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Sitter Profile Image: Sateela H.
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Sitter Profile Image: Sateela H.
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11. Sateela H.

Passionate Pet Enthusiast
Chicago, IL, 60616
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per visit

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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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12. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.2 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 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!

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Sitter Profile Image: Olivia M.
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Sitter Profile Image: Olivia M.
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13. Olivia M.

Hi I’m Olivia and I love your pets
Chicago, IL, 60616
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$20
per visit

Always love having Olivia drop in on my Biscuit 🥰

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Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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14. Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$25
per visit

Kayla did a good job checking in on my cats while I was away. She refilled their water, changed their litter, cleaned up vomit, and played with them.

Confirmed availability: Easter Weekend
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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15. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
241 reviews
104 repeat clients
from
$45
per visit

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

Sitter Profile Image: Dee M.
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Sitter Profile Image: Dee M.
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16. Dee M.

Hyde Park Dog Lover
Grand Boulevard, Chicago, IL, 60653
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$20
per visit

Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I know she will get her exercise when she is with Dee. I cannot express enough how much I appreciate Dee & the genuine loving care she gives my little girl, Déjà. Highest recommendations from us!

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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
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
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!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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18. Masheika S.

Rover 101
All around animal lover 💜🐾
Chicago, IL, 60653
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
21 repeat clients
from
$35
per visit

Masheika did an awesome job taking care of our cats! Very punctual, great photo updates, and our cats were very happy with the care they received. We would absolutely hire Masheika again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Jani M.
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Sitter Profile Image: Jani M.
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19. Jani M.

Experienced Care/Flexible Schedule
Douglas, Chicago, IL, 60616
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
8 years of experience
from
$20
per visit

About: Hello there, Im Jani 👋🏾Pleasure to Meet you. Growing up, I have been so fortunate enough to care for many animals. From bunnies, guinea pigs, to various breeds of cats and dogs & even exotic fish & turtles. My family and I would even visit farms, zoos & aquariums often, so being around animals is definitely apart of my life & I absolutely wouldn’t want it any other way. :) Now as an adult, I have found myself caring for some sort of beautiful animal. As you see in my profile, I have a ton of experience with various cats and dogs. I lived with my feline buddy, Tiger, for 4 years before having to give Tiger up for adoption do to moving out of state. It was a very difficult decision, but he is in a good home with an amazing woman who continues to update me and send me pictures of him. 🤗 My favorite way to care for my animals are to learn what they are interested in & incorporating more fun & joyous experiences for them. I find myself interested in learning different animal breeds, their behavioral traits, and how to add more love into their lives. I believe this app brings such an extraordinary opportunity to learn, grow & experience life through different homes while also getting to travel to amazing places. I have always had a passion to help others. I am excited to care for your animals while also guaranteeing I will do my absolute best to ensure your needs are met & you have a pleasant experience with me pet sitting for you. ✨ I truly adore all animals !! Any shape or size! 🐩 I promise to give endless belly rubs and always ensure a safe environment for your fur babies. 🐾 I am trustworthy, responsible & more than capable to take on any task ! I have a very flexible schedule, I choose my work hours each week & am always available to bring my work with me on my laptop if doing any overnight stays. I am typically available 6 a.m. - 10 p.m. to walk your dogs and check up on your fur babies! Unfortunately, I do not offer services in my home. The only services I am offering in home is overnight pet sitting that would take place at the clients home. Keep in mind that, I keep my calendar updated on the app. 😊 I would be more than happy to care for your furry friend while you’re away. I assure you they will be well taken care of and that I will keep my belongings tidy and clean for overnight stays. Please let me know if you would like daily photos or videos of your fur babies while you’re away and I will gladly send them to you. 📸 Moreover, I am available in the afternoons to evenings if you would like to chat over the phone or do a video call before making your decision. I would love to personally hear what your expectations are for your pet(s) to ensure you are comfortable and satisfied with me caring for them. 😊 With new clients, I like to schedule a meet and greet before accepting a booking request. Thanks for understanding! Ask me any questions you’d like. ✨ I look forward to hearing from you soon😊

Confirmed availability: Easter Weekend
Sitter Profile Image: Joshua M.
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Sitter Profile Image: Joshua M.
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20. Joshua M.

Fun loving animal person
Chicago, IL, 60653
0.2 mi. away
Drop-In Visits, Dog Walking
2 years of experience
from
$17
per visit

About: I have been a dog owner and have had dogs and some cats since the age of 5. I have cared for, paid, and even traveled with a Shih Tzu breed that I currently have, and have had many Doberman Pinschers in the past. I feed, bathe, take them to the park for play and walk, and even watched my neighbor's pets while they were gone. I'm currently working part-time remotely on the days of Monday-Friuay. However, I do have time to take dogs for a walk on weekends after 10 am. I have a fenced yard and a friendly Shih Tzu who is people-friendly and also makes sure she is not exposed to objects in the yard or house. I also have a bed in the living room and her own in my room for comfort. She also takes Heartguard for prevention of fleas, ticks, and ring worm and is rabies vaccinated.

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Dog lovers in Oakland, Chicago, IL love pet sitters on Rover.com. Over 7915 pet owners have reviewed pet 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 pet sitting in Chicago can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakland, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Oakland, Chicago who can provide the care your pet needs, when they need it.

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