Pet Sitting & Drop Ins in Douglas, 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
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Niko F.
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Sitter Profile Image: Niko F.
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1. Niko F.

Star Sitter
Ensuring your pets safety/happiness
Lower West Side, Chicago, IL, 60616
2.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
21 repeat clients
from
$22
per visit

Thank you so much for all the photos and updates! Baker was happy to have us home but with your care he was well looked after. If anyone is looking for a cat sitter I can highly recommend you as the affection and play time you give was well worth every penny. Thank you for taking care of our boy.

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

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

Crystal is wonderful! She looked after my beloved cat during drop-in visits. We had a nice meet-and-greet, and I felt very comfortable leaving my Simon in Crystal's care while I was away for a few days. She sent detailed updates each day and made a lot of effort in making sure he was cared for. I look forward to booking with her again in the future!

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.

Star Sitter
Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
3.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 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.

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

Emily was so great with our cats! She always sent photo updates along with her check-in messages and she was flexible and able to come out again when the automatic feeder got jammed. I would definitely recommend Emily’s services and happily rebook her as a cat sitter!

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

Star Sitter
Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
79 reviews
33 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!

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

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
0.8 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: Ashleigh H.
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Sitter Profile Image: Ashleigh H.
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7. Ashleigh H.

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
1.8 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: Dalila E.
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Sitter Profile Image: Dalila E.
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8. Dalila E.

Rover 101
Star Sitter
PET SPECIALIST
Chicago, IL, 60616
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
193 reviews
85 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 :)

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Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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9. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
1.6 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Magdalena G.
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Sitter Profile Image: Magdalena G.
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10. Magdalena G.

Ensuring Expert Care for Every Dog!
Chicago, IL, 60605
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$60
per visit

I booked a house sitting service. I had to travel for work, and with my oldest pet Logan, I have a very difficult time leaving him. He has a lot of health issues, and a very extensive care routine. Magda was not only able to provide him all of the attention he needs, but also followed his care plan and went above and beyond. He became comfortable with her very quickly. She sent picture and frequent text updates and that put my mind at ease. Definitely will book her again!! Thank you so much Magda!!!

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Sitter Profile Image: Ericka J.
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Sitter Profile Image: Ericka J.
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11. Ericka J.

Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$25
per visit

Ericka helped us while we were on vacation by checking on our cat, making sure she had fresh food/water and a clean litter box. She sent us pictures of our kitty and gave us updates at every check-in. Would definitely recommend her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Julianne F.
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Sitter Profile Image: Julianne F.
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12. Julianne F.

Nurturing Care Giver & Animal Lover
Lower West Side, CHICAGO, IL, 60616
2.1 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
74 reviews
21 repeat clients
from
$23
per visit

Julianne was so sweet and took such great care of our kitty while we were away! Her communication was excellent - we really appreciated her detailed updates and loads of pictures too! Would definitely recommend booking with her :)

Sitter Profile Image: Addy T.
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Sitter Profile Image: Addy T.
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13. Addy T.

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

Addy was awesome!!! Thank you so much!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Olivia F.
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Sitter Profile Image: Olivia F.
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14. Olivia F.

Pet Lover, Used to High Need Dogs
Near South Side, Chicago, IL, 60616
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
5 repeat clients
from
$25
per visit

Olivia was great to work with! Her updates on our drop-ins were always right on time and she and our senior dog got along really well. We felt at ease knowing she was there to check in on our dog while we were away.

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Sitter Profile Image: Janessa M.
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Sitter Profile Image: Janessa M.
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15. Janessa M.

I've arrived, The best sitter ;)
Bridgeport, Chicago, IL, 60608
1.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
35 reviews
11 repeat clients
from
$18
per visit

Janessa was an amazing sitter for my cats. She gave me detailed reports and followed all of my instructions. I will be using her again! Highly recommend her services.

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Sitter Profile Image: Katie "Anni" W.
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Sitter Profile Image: Katie "Anni" W.
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16. Katie "Anni" W.

Welcoming all fur babies :)
Near South Side, Chicago, IL, 60616
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$20
per visit

I have booked her multiple times for my dogs when I go on vacation and business trips. She always makes them feel comfortable right away and I can tell they are having a good time when I see their pictures together. I would recommend her to anyone trying out Rover!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Courtney H.
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Sitter Profile Image: Courtney H.
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17. Courtney H.

Animal lover, current dog owner
Chicago, IL, 60608
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
25 years of experience
from
$17
per visit

About: I’ve taken care of various dogs for the past 25 years - either through dog sitting or owning my own dogs. Have vast experience feeding, walking, taking care of pups! I have the ability to work from anywhere, so I can be very flexible with schedules! Also, my after hours are currently flexible as well! All the things your pup needs! Walking, feeding, and most importantly, snuggling. Would just want to know a bit about how your pup behaves, and I can adapt!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Olivia M.
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Sitter Profile Image: Olivia M.
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18. Olivia M.

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

Always love having Olivia drop in on my Biscuit 🥰

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: jiehui l.
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Sitter Profile Image: jiehui l.
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19. jiehui l.

I treat all pet like my own pet
Bridgeport, Chicago, IL, 60616
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$20
per visit

He is really nice guy! He has a lot of patience and kind. Once our family don’t have time take care our dogs. Jiehui Li help us walk dogs and take care. It’s two huge fat German Shepherd Dogs. He has his own way to treat the animals. Oh, by the way he has two adorable cats.

Sitter Profile Image: Matt C.
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Sitter Profile Image: Matt C.
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20. Matt C.

Rover 101
4 parks within walking distance!
Armour Square, Chicago, IL, 60616
0.7 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
125 reviews
21 repeat clients
from
$20
per visit

By far, Matt has been the best dog sitter I've had. You can tell how much he loves animals. My dogs really like him. He takes care of them like they are his own. Matt is an A+ dog sitter!

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When it comes to pet sitting, dog owners in Douglas, Chicago, IL love Rover.com. Over 7915 owners have reviewed sitters in Chicago, giving them an average rating of 4.9/5. The cost of pet sitting in Douglas may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Douglas, 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 Douglas, Chicago who can provide the care your pet needs, when they need it.

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