Pet Sitting & Drop Ins in Loop, 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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Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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1. Katie M.

Star Sitter
Long time animal lover
Near North Side, Chicago, IL, 60610
2.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
173 reviews
58 repeat clients
from
$20
per visit
Profile image

Katie was punctual, easy to communicate with, and very professional! She did a stop by for our puppy and was amazing with her! Would absolutely use Katie again!

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

Star Sitter
Ensuring your pets safety/happiness
Lower West Side, Chicago, IL, 60616
1.6 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
45 reviews
28 repeat clients
from
$22
per visit
Profile image

Niko is awesome, definitely made sure my kitty was comfortable and taken care of. I had some bad experiences with sitters and am glad to find someone dependable!

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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
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
159 reviews
28 repeat clients
from
$20
per visit
Profile image

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: Joris V.
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Sitter Profile Image: Joris V.
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4. Joris V.

Patient and energetic animal lover!
Chicago, IL, 60607
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$10
per visit

The best thing about Joris is he has a bit of the personality of a dog: loyal, sociable, and affectionate. These make him the most reliable person for me to lean on when I need someone to take care of my pet. Not only does he do a wonderful job at taking care of your pet's needs, but he also truly enjoys it. A walk? Of course. A run? No problem! Attention? Say less.

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Sitter Profile Image: Abigail R.
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Sitter Profile Image: Abigail R.
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5. Abigail R.

Here to care like they’re my own!
Chicago, IL, 60661
1.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$10
per visit
Profile image

Abigail was amazing in taking care of Rosie and provided great communication throughout. Had no worries in leaving Rosie with her as she went above and beyond. Highly recommend.

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Sitter Profile Image: Jean T.
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Sitter Profile Image: Jean T.
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6. Jean T.

Star Sitter
Your pet’s new best friend!
Chicago, IL, 60601
0.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
4 repeat clients
from
$19
per visit
Profile image

Jean looked after our two cats for three days during the holidays. He was communicative, professional and attentive. I definitely recommend his service and will book him again.

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Sitter Profile Image: Shannon M.
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Sitter Profile Image: Shannon M.
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7. Shannon M.

Star Sitter
All Animals Welcome!
Loop, Chicago, IL, 60601
0.7 mi. away
Drop-In Visits
5.0 out of 5 stars
34 reviews
10 repeat clients
from
$20
per visit
Profile image

Shannon was great with our cat! She came home and didn’t even seem like she missed us. She treated our home as her own and we came home to a clean house and a very happy kitty. Will definitely be booking with Shannon again!

Sitter Profile Image: Emily A.
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Sitter Profile Image: Emily A.
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8. Emily A.

Star Sitter
South Loop pet expert!
Near South Side, Chicago, IL, 60605
1.0 mi. away
Drop-In Visits
5.0 out of 5 stars
176 reviews
62 repeat clients
from
$20
per visit
Profile image

We have used Emily twice so far, and we LOVE her! She is very accommodating, and is so good to our fur babies. We have been blessed to have found her!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Yingyue L.
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Sitter Profile Image: Yingyue L.
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9. Yingyue L.

Star Sitter
Seasoned sitter 🐕 🐈 Full-time WFH
Chicago, IL, 60611
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
3 repeat clients
from
$22
per visit
Profile image

Yingyue is amazing. She accepted my last minute request, and she’s super responsive and communicative as well. She followed my instructions, asked all the appropriate questions, and kept me updated throughout the entire visit. I definitely recommend Yingyue and felt comfortable putting my pup in her care.

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Sitter Profile Image: Toni P.
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Sitter Profile Image: Toni P.
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10. Toni P.

Rover 101
Star Sitter
Professional pet care
Chicago, IL, 60601
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
52 reviews
17 repeat clients
from
$24
per visit
Profile image

Thank you Toni for your outstanding support to my two precious cats Jacks and Lulu! Toni was able to step in at the last hour to support an urgent need to check on my babies when I was having travel delays getting back home. What a feeling of relief and surety knowing that I had someone reliable and a real cat whisper who is a natural at putting my two anxious, YOUNG cats at ease. Although they are super lovable and friendly, they are very timid around new people. Toni was able to break them out of their shell really fast and made them super comfortable around her during the first drop-in, which is underheard of, lol! After loads of attention, treats and food, she had them purring in delight. I am appreciative of Toni especially going the extra mile to clean of the mess they made in my absence. Broken ornament glass can lead to cuts and injuries, so I appreciate her for making their safety a priority. If she is free next time we need a drop in or sitter, she'll be the first one I call. Jacks and Lulu really do love her :-) !!!

Sitter Profile Image: Grace T.
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Sitter Profile Image: Grace T.
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11. Grace T.

Dog Lover!
Loop, chicago, IL, 60605
0.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
63 reviews
31 repeat clients
from
$20
per visit
Profile image

Grace has been a regular dog walker for us for a couple months now and we're really happy to continue working with her. She's professional, easy to communicate with, and does a great job spending time with our dogs. We appreciate her greatly. I would recommend her highly.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Daniela B.
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Sitter Profile Image: Daniela B.
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12. Daniela B.

Dog lover 🐾
Loop, Chicago, IL, 60601
0.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$19
per visit

Daniela is the best! I have known her for a while, and she is a true dog lover. She always takes cares for Millie (my greyhound) when I'm gone, and I can go peacefully because she loves her. Every time Millie sees Daniela starts to jump and bark of happines, and start to bring her toys and I just love to see her so happy. Daniela is very responsible, methodical, and kind, so she is the best dog sitter. I can put my hands on fire for her. The best part about when I'm gone is that she sends me pictures of Millie so I can see her calm face. I can't get that of any other person. Thanks Daniela for all your help! Bárbara A.

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Sitter Profile Image: Cathie v.
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Sitter Profile Image: Cathie v.
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13. Cathie v.

Rover 101
Star Sitter
I love animals!
Loop, Chicago,, IL, 60601
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
5 repeat clients
from
$25
per visit
Profile image

Cathie is amazing and would certainly book regularly. She gives such personal care and attention and I felt significantly more comfortable with her watching over my pet with drop in visits.

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Sitter Profile Image: Jillian T.
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Sitter Profile Image: Jillian T.
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14. Jillian T.

Flexible work from home dog mom!
Near North Side, Chicago, IL, 60654
0.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
32 reviews
7 repeat clients
from
$20
per visit
Profile image

Although I ended up not needing Jillian, she was very polite and responsive and I look forward to using her for future dog sitting/walking services.

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Sitter Profile Image: Meghan H.
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Sitter Profile Image: Meghan H.
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15. Meghan H.

Quality & Cuddly Cat and Dog Care
Near South Side, Chicago, IL, 60605
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
6 repeat clients
from
$20
per visit
Profile image

Meghan was fantastic! This was my first time with Rover and she made the process comfortable and easy! She sent me daily updates and pictures of my cats and I came home to happy kitties. Highly recommend Meghan!!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Darcy P.
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Sitter Profile Image: Darcy P.
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16. Darcy P.

Ace Ventura for pets 🐶😻
Chicago, IL, 60605
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
163 reviews
85 repeat clients
from
$23
per visit
Profile image

Darcy was great! She was very communicative, shared many pictures and details of her check on my kitty. She even cleaned up an accident she had - really went above and beyond! I will definitely try to book with her again!

Sitter Profile Image: Jason C.
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Sitter Profile Image: Jason C.
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17. Jason C.

Star Sitter
Friendly dog walker from the UK
Loop, Chicago, IL, 60605
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
90 reviews
27 repeat clients
from
$18
per visit
Profile image

Jason is such a wonderful asset for our family’s lifestyle! The pups love him, he’s flexible, extremely communicative and dependable! There’s a reason he has so many Rover clients, he’s the best!

Sitter Profile Image: Sandra T.
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Sitter Profile Image: Sandra T.
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18. Sandra T.

Rover 101
Star Sitter
Love and care given as I do my own!
Loop, Chicago, IL, 60602
0.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
414 reviews
122 repeat clients
from
$22
per visit
Profile image

Sandra was phenomenal with our two cats, one young and one old. We are so happy to have found her. Plus, when our flight home was cancelled and we were delayed overnight, Sandra made herself available at the last minute for an additional visit. Sandra is the best.

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Sitter Profile Image: Alyssa L.
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Sitter Profile Image: Alyssa L.
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19. Alyssa L.

Star Sitter
Animalshelter staff ready for walks
Loop, Chicago, IL, 60605
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
10 repeat clients
from
$22
per visit

Alyssa makes a great pet sitter because she has lots of experience walking all types of dogs. She is very knowledgeable about reading dog behavior and very alert about any potential dangers or threats when passing other people or dogs. Alyssa is very punctual and will always show up when she says she will. Alyssa is hard working and honest. Your pets will be in great hands with Alyssa.

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Sitter Profile Image: Sylvia W.
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Sitter Profile Image: Sylvia W.
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20. Sylvia W.

Star Sitter
Flexible Schedule, cats and dogs!
Chicago, IL, 60605
0.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
7 repeat clients
from
$18
per visit
Profile image

Sylvia always dropped in around the agreed upon time, took pictures, and gave detailed updates on how TC was doing. It was a great and easy experience and I highly recommend!

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When it comes to pet sitting, dog owners in Loop, Chicago, IL love Rover.com. Over 333 owners have reviewed sitters in Loop, Chicago, giving them an average rating of 4.9/5. The cost of pet sitting in Loop 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.

Rover.com is the simple, savvy way to find and book Loop, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Loop, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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