Pet Sitting & Drop Ins in Armour Square, 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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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
1.3 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
24 repeat clients
from
$22
per visit

Niko was attentive and sent detailed messages regarding his visits with my pet. He took good care of my car. I would highly recommend his services!

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
1.5 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 amazing! She was very communicative, punctual, and the kitties seemed happy and well fed when we got back. I would absolutely book again!

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Sitter Profile Image: Shimmy G.
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Sitter Profile Image: Shimmy G.
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3. Shimmy G.

Star Sitter
I love my pups & I’ll love yours!
Near South Side, Chicago, IL, 60605
1.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
141 reviews
27 repeat clients
from
$20
per visit

Shimmy is wonderful with my pup! She gives him lots of great play time and takes great photos. I trust that he is in good hands when Shimmy comes over!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Abigail R.
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Sitter Profile Image: Abigail R.
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4. Abigail R.

Here to care like their my own!
Loop, Chicago, IL, 60606
2.8 mi. away
Drop-In Visits, Dog Walking
2 reviews
from
$10
per visit

As a lifelong pet owner, Abigail possesses a wealth of experience in dealing with pets, and she is very caring and attentive to their needs.

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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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5. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
0.6 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: Michael D.
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Sitter Profile Image: Michael D.
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6. Michael D.

Star Sitter
Dog Lover Ready to Love Your Dogs
Chicago, IL, 60609
2.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
10 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!

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
1.3 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.

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

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Sitter Profile Image: Nicole K.
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Sitter Profile Image: Nicole K.
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9. Nicole K.

Pet Loving College Student
Chicago, IL, 60608
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$15
per visit

1st time away from my kids for more than two nights & also this was my 1st time using Rover. Anxiety is running super high but everything went off without a hitch. Nicole was extremely professional an took great care of my kids! I will be using Rover & hoping that I can book Nicole again.

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

Star Sitter
Sloop couple saving for a wedding
Near South Side, Chicago, IL, 60605
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 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 😊

Sitter Profile Image: Matt C.
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Sitter Profile Image: Matt C.
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11. Matt C.

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

Matt is an amazing, responsive dog sitter. He watches my Shiba a few times each month when I'm out of town. I can relax knowing that my little buddy is in the care of such a trustworthy person. Matt is an enthusiastic animal lover. I highly recommend him to everyone I know!

Sitter Profile Image: Kristi T.
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Sitter Profile Image: Kristi T.
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12. Kristi T.

Rover 101
Ready to swap secrets w/ your pets!
Chicago, IL, 60608
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
34 reviews
11 repeat clients
from
$20
per visit

Kristi was fantastic! She really made my little Monty feel loved while I was away. I could see it in the many pictures and videos that she sent me. She showed up on schedule and let me know if she needed to deviate. She did an all around great job with feeding, medication, and cuddling. I would hire her again and recommend her to others without reservation.

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Sitter Profile Image: Sujae V.
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Sitter Profile Image: Sujae V.
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13. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
1.0 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: Amy C.
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Sitter Profile Image: Amy C.
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14. Amy C.

Animal enthusiast with extra ♥️
Chicago, IL, 60605
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
3 repeat clients
from
$20
per visit

Amy was absolutely amazing with caring for our pets and their various needs. Very helpful, kind, and communicative. Couldn’t have asked for better care of our animals! Would highly recommend!

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Sitter Profile Image: Ericka J.
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Sitter Profile Image: Ericka J.
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15. Ericka J.

Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
1.2 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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16. Julianne F.

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

She’s amazing! We always get the most thorough report card for our two babies and she recently watched both of our cats for a week while we were out of the country and she arrived twice a day at the time we requested and sent lots of pics and played with our fur babies in the most fun and loving way! We felt 100% at ease having her here and that our cats were well taken care of! Forgot to mention one of our cats is senior and needs meds and lots of love and she was always in amazing shape and cared for when we returned…not stressed at all, which never happens after long times away! We will continue to use Julianne and are so grateful for her!

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Sitter Profile Image: Janessa M.
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Sitter Profile Image: Janessa M.
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17. Janessa M.

I've arrived, The best sitter ;)
Bridgeport, Chicago, IL, 60608
1.1 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 always does an amazing job caring for my cats and ensuring that I don’t have to worry about their well-being when I’m not home. They have grown to love her and climb all over her at every visit.

Sitter Profile Image: Addy T.
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Sitter Profile Image: Addy T.
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18. Addy T.

Experienced with cats and dogs!
Chicago, IL, 60616
0.8 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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19. Olivia F.

Pet Lover, Used to High Need Dogs
Near South Side, Chicago, IL, 60616
1.0 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.

Sitter Profile Image: Zoe K.
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Sitter Profile Image: Zoe K.
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20. Zoe K.

Hello. My name is Zoe Kinser.
Armour Square, Chicago, IL, 60616
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
35 reviews
12 repeat clients
from
$16
per visit

As usual, Zoe is phenomenal. One of my cats got sick (from eating too much of a new brand of food that I had left them before going out of town) while Zoe was watching them recently, and Zoe immediately took care of it, let me know, cleaned up the mess, and monitored how much they ate afterward-- which is really above and beyond. Unlike other sitters I've booked through Rover, Zoe would always leave detailed reviews, including multiple pictures and videos. She'd always let me know how my cats were behaving each day she stopped by and if anything was off. I never worry when I'm traveling, because I know my babies are in good hands.

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

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Pet parents in Armour Square, Chicago, IL love dog sitters on Rover.com. 7915 owners have reviewed sitters in Chicago, giving them an average rating of 4.9/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Armour Square pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Armour Square, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Armour Square pet sitters and avoid the kennel.

Drop-In Visits