Pet Sitting & Drop Ins in West Town, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Justin L.
1.
Active dog lover with free timeWest Town, Chicago, IL, 60642
Drop-In Visits, Dog Walking

Justin was so friendly and communicative! He checked in on my cat and even stayed to play. Highly recommend. (more)

from
$17
per visit
Confirmed availability: Memorial day
Autumn F.
2.
Gentle, Engaging, and Hard to FazeNear West Side, Chicago, IL, 60607
Drop-In Visits, Dog Walking

autumn was professional, punctual and all around showed great attention and patience with beare. i loved the update she gave and appreciate her flexibility and … (more)

from
$25
per visit
Confirmed availability: Memorial day
Maureen K.
Compassionate and reliable!West Town, Chicago, IL, 60642
Dog Boarding, Drop-In Visits, Dog Walking

Maureen was amazing! Our cat is usually pretty shy, but warmed right up to Maureen. We got incredibly detailed reports each day, along with the most beautiful p… (more)

from
$22
per visit
Calendar Recently Updated
Amy B.
4.
Amy 
Verified Enhanced Background Check
Home full-time, active, responsibleNear North Side, Chicago, IL, 60610
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

My fiance and I had a great experience with Amy's check-ins while we were away for a weekend vacation. My cat usually takes a little time to warm up to new peop… (more)

from
$27
per visit
Confirmed availability: Memorial day
Kevin C.
5.
Pawsitively the bestWest Town, Chicago, IL, 60642
House Sitting, Drop-In Visits, Dog Walking

As a owner of two rough riders (pit-bulls), it was difficult for me to find a dog sitter who was capable of handling them whenever I travel. They are times wher… (more)

from
$25
per visit
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Loving dog mom and dog aunt!Logan Square, Chicago, IL, 60647
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I’ve raised and trained my brother’s Weimaraner since she was 6 weeks old. Now I have a 1.5 year old German Shorthair Pointer heartthrob of my own. I… (more)

from
$19
per visit
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7.
Extra Care and LoveWest Town, Chicago, IL, 60622
House Sitting, Drop-In Visits, Dog Walking

Ashley was wonderful dropping in to take care of my cats for a few days. I appreciated all the pictures and texts to let me know things were going fine! She was… (more)

from
$16
per visit
Confirmed availability: Memorial day
8.
Dogs are amazing. Mic drop!West Town, Chicago, IL, 60647
House Sitting, Drop-In Visits, Dog Walking

I wish I could give Ania more stars! She was very responsive and came over short notice to check in on my puppy. She sent lots of pictures and was very respectf… (more)

from
$25
per visit
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I cannot wait to meet your dogs!Logan Square, Chicago, IL, 60647
House Sitting, Drop-In Visits, Dog Walking

We couldn’t have picked a better match for us and our 3 kitties! Shannon was phenomenal. She went above and beyond. I now know who will be babysitting our cats … (more)

from
$24
per visit
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10.
Wherewoof & KatzWest Town, Chicago, IL, 60622
Drop-In Visits, Dog Walking

This was my first time using Rover and I will definitely be booking through here again! Ariel was so lovely to work with and I came home to happy cats and a re… (more)

from
$20
per visit
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Dog lovers seeking more company.West Town, Chicago, IL, 60622
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Alex and Lupe are great! They have watched my pup Leon on multiple occasions. They’re always great with Leon and send me frequent updates and cute pics! Leon an… (more)

from
$20
per visit
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Operation: Fun with meWest Town, Chicago, IL, 60622
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Stephanie was incredible!!! She kept me in constant contact and was so sweet by providing tons of pictures of my baby and even videos! I came home to the happie… (more)

from
$25
per visit
Confirmed availability: Memorial day
13.
Nurse & Animal lover!West Town, Chicago, IL, 60622
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Monique and I have been friends for 20 years, she's an amazing lady. She has a brilliant mind, a caring heart and peaceful soul. She a loyal and trustworthy fri… (more)

from
$15
per visit
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14.
Certified dog lover!West Town, Chicago, IL, 60622
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Leaving your dog is never easy, but leaving them with Rebecca feels like family! She will give your pup all the love and attention they deserve and give you pea… (more)

from
$30
per visit
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15.
Liz 
Verified Background Check
Rover 101
I can’t wait to meet your pup!West Town, Chicago, IL, 60622
House Sitting, Drop-In Visits, Dog Walking

Ok, Liz is amazing. She took care of my border collie who was quite the handful. He once ripped the pocket off of my pants when I had the leash in my pocket, … (more)

from
$20
per visit
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16.
Caring for pets is a passion!West Town, Chicago, IL, 60622
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Laura is one of the most caring pet lovers I know! She's watched my dog, Murphy many times over the last 3 years. She's walked Murphy and had overnight visits w… (more)

from
$17
per visit
Confirmed availability: Memorial day
17.
Warrior Cat/Dog Fan @ your service!West Town, Chicago, IL, 60612
House Sitting, Drop-In Visits, Dog Walking

Adriana is the best cat sitter we have found in Chicago! We’ve been utilizing her services for the past year when we leave for weekend trips and vacations. Alwa… (more)

from
$16
per visit
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18.
Dog Walker for 4 YearsWest Town, Chicago, IL, 60622
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Rachel was amazing! Our kitties and dog really loved her. We were out of town for a week and it's kinda nerve-wracking to leave pets at home. But we were totall… (more)

from
$20
per visit
19.
Pro Dog Lover Ready to Serve!!!West Town, Chicago, IL, 60622
House Sitting, Drop-In Visits, Dog Walking

Dakota is a great and loving individual, and dogs have a special place in her heart. She is highly responsible and would be a perfect dog sitter. (more)

from
$25
per visit
Confirmed availability: Memorial day
20.
Meet your pets new best friend.West Town, chicago, IL, 60622
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

To sum it up best, if I were a dog I will KILL to come back as a dog, (or any animal for that matter) Roger had. He is BEYOND loving and does make the very best… (more)

from
$20
per visit

Rover also offers Pet Sitting & Drop Ins in:

In West Town, Chicago, IL, dog lovers trust Rover.com for their pet sitting needs. Over 520 pet owners have reviewed pet sitters in West Town, Chicago, giving them an average rating of 5.0/5 stars. Booking pet sitting in West Town can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book pet sitting in Chicago on Rover? Check out our average pet sitting rates to get an idea before reaching out and beginning a conversation with a sitter.

Rover.com is the simple, savvy way to find and book West Town, 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 West Town, 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 pet sitter or dog walker. 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 West Town, 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: