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
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Presidents' Day Weekend
Mandy M.
1.
I will love your pets like my own!Near North Side, Chicago, IL, 60611
Drop-In Visits, Dog Walking

Mandy is my go-to sitter. She gets my kitty to come out of his shell and he clearly really enjoys her company! Very responsive, always does a great job. (more)

from
$25
per visit
Confirmed availability: Presidents' Day Weekend
Munder S.
2.
Your pet needs some me time tooWest Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking

Munder is the sweetest. They’re reliable and made me feel at ease using this service for the first time. They followed my instructions exactly and communicated … (more)

from
$34
per visit
Confirmed availability: Presidents' Day Weekend
Anna L.
3.
Dog + Cat Care • Sr + Special NeedsNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

Anna was so great!! We couldn’t recommend her more. She watched our cat for the weekend and was so communicative and cared so much about Snickers (more)

from
$50
per visit
Confirmed availability: Presidents' Day Weekend
Kyla H.
4.
Miss having pets in my home, share?Chicago, IL, 60610
Drop-In Visits, Dog Walking

Kyla is so amazing with my pups! She is incredibly reliable and always makes me feel so at ease when she’s with my boys. Could not recommend her enough! (more)

from
$20
per visit
Calendar Recently Updated
Lindsay J.
Cat mom and animal loverNear North Side, Chicago, IL, 60610
House Sitting, Drop-In Visits

Lindsay was great with the cats! She was very timely, and communicated everything with me. Would definitely use her again. (more)

from
$25
per visit
Calendar Recently Updated
Extra caring pet lover!Loop, Chicago, IL, 60605
Drop-In Visits

Always dependable, and always willing to help out last minute if available. Came through for me after I lost one of my kitties right before Thanksgiving and wan… (more)

from
$24
per visit
Confirmed availability: Presidents' Day Weekend
7.
Caring, attentive pet lover!Loop, Chicago, IL, 60605
Drop-In Visits

Sophie did such a great job watching my cat Ashe over the holiday. Her updates were detailed and included several photos! I will definitely rebook with Sophie a… (more)

from
$20
per visit
Confirmed availability: Presidents' Day Weekend
8.
Downtown, Loving pet sitterChicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Cody took an amazing care of my dog while I was out of town. Great communication, always prompt responses, showed up on time and took lots of pictures! I highly… (more)

from
$25
per visit
Confirmed availability: Presidents' Day Weekend
9.
Dogs are the Best!Chicago, IL, 60605
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Shawn has been a friend of mine and my dogs for over 20 years. My dogs jump up the second he walks in the door. Over the years Shawn has been the first friend I… (more)

from
$20
per visit
Calendar Recently Updated
10.
Your pet’s new best friend!Chicago, IL, 60601
Drop-In Visits, Dog Walking

Jean is such a great person. He is so friendly with dogs, he used to help me take care of Croissant(my dog) and Croissant loved him so much. He is pretty famili… (more)

from
$20
per visit
Confirmed availability: Presidents' Day Weekend
Active and outdoorsy animal loverLoop, Chicago, IL, 60601
House Sitting, Drop-In Visits, Dog Walking

Mackenzie was timely, professional, and took amazing care of my fur baby even for the short amount of time that I had her come! So grateful for her help and I’l… (more)

from
$20
per visit
Calendar Recently Updated
12.
The Dog-Loving Law StudentLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Sharon walked our pup Montgomery this evening, relatively last minute. She sent multiple photos from start to finish, and then sent a wonderful "report card" t… (more)

from
$39
per visit
Calendar Recently Updated
13.
Loves all cats in West Loop!Near West Side, Chicago, IL, 60661
Drop-In Visits

Adam to the rescue once again! He is my favorite rover by far. He take time to get to know our pets and caters to their every desire! He is always prompt and th… (more)

from
$20
per visit
Confirmed availability: Presidents' Day Weekend
I am a girl who loves animals!Loop, Chicago, IL, 60605
Drop-In Visits, Dog Walking

Amazing job went above and beyond what was expected (more)

from
$25
per visit
Confirmed availability: Presidents' Day Weekend
15.
Here to love your fur babies!Chicago, IL, 60601
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Meghan is fantastic with cats and dogs alike and truly shows her care by going the extra mile. She sends updates along with pictures to keep you in the loop and… (more)

from
$40
per visit
16.
Friendly dog walker from the UKLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Jason was able to stop by on super short notice when I saw that our cats hadn't eaten from their automatic feeder all day. I couldn't see the cats via the petc… (more)

from
$18
per visit
Confirmed availability: Presidents' Day Weekend
17.
I love all animals!Near West Side, Chicago, IL, 60661
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Alexa did so great and was very responsive prior, during, and after the visit with my dog. Would 100% recommend to anyone who needs animal help! (more)

from
$27
per visit
Calendar Recently Updated
Your fur babies are my #1 priority!Loop, Chicago, IL, 60605
Drop-In Visits, Dog Walking

Lilianna did a wonderful job watching over my dog Luna while I was away for the week on vacation. She made sure to really care for Luna as if she were her own! … (more)

from
$20
per visit
Calendar Recently Updated
19.
Work from home⚖️ | Treats. Play. ❤️Loop, Chicago, IL, 60607
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

We contacted Alison for the first time. She was amazing. She came early to meet Dezzy, sent photos on each visit and spend good quality time with him. She to… (more)

from
$50
per visit
Calendar Recently Updated
20.
Love and care given as I do my own!Loop, Chicago, IL, 60602
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

We are so grateful for Sandra! We have booked multiple times and she always provides great care and attention for our cat. She is a excellent and frequent commu… (more)

from
$22
per visit

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.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Loop, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including:

Drop-In Visits