Pet Sitting & Drop Ins In Near North Side 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.

Search Results

Confirmed availability: Memorial Day
Eva A.
1.
Eva 
Verified Enhanced Background Check
Flexible and loving pet-sitter!Near North Side, Chicago, IL, 60611
Drop-In Visits

Eva is the absolute best! My cat has anxiety when I am not with him but Eva clearly knows how to handle the situation, she spent a long time playing with my cat… (more)

from
$17
per visit
Kari T.
2.
I love dogs, plain and simple!Near North Side, Chicago, IL, 60611
House Sitting, Drop-In Visits, Dog Walking

Kari was wonderful with my headstrong pittie, Ava. She was very flexible and understanding with my silly schedule that changed often. Definitely recommend her! (more)

from
$25
per visit
Calendar Recently Updated
Tori G.
3.
PA student who loves to dog sit!Near North Side, Chicago, IL, 60654
Drop-In Visits, Dog Walking

Tori was great! Very friendly, responsive and my Great Dane pup loved her! (more)

from
$20
per visit
Calendar Recently Updated
Shannon O.
Animal Care: Dogs, Cats & AquaticsNear North Side, Chicago, IL, 60610
House Sitting, Drop-In Visits, Dog Walking

Shannon is a gem! She always showed up with a smile, sent me great photos and updates everyday during her walks. My dog loves her! She’s super easy to communica… (more)

from
$15
per visit
Confirmed availability: Memorial Day
Sharon G.
5.
Dog lover and owner my whole life!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Thank you Sharon for your superb hospitality. Boots and Sadie enjoyed your visit. I highly recommend Sharon as a professional and reliable dog sitter/walker. (more)

from
$17
per visit
Confirmed availability: Memorial Day
Active dog snugglers and walkers!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I ran my own pet-sitting business for five years in high school. I have owned dogs my whole life! My husband I are flexible and both work from home a… (more)

from
$30
per visit
Calendar Recently Updated
7.
Dog/Kitty caretaker full time!Near North Side, Chicago, IL, 60610
House Sitting, Drop-In Visits, Dog Walking

Our first time having Rose as our cat sitter, but definitely not the last. Rose took extra time to get to know our less-than-open-to-new-people cat. Thank you, … (more)

from
$22
per visit
Confirmed availability: Memorial Day
Let me share my love with your pup!Lincoln Park, Chicago, IL, 60614
Drop-In Visits, Doggy Day Care, Dog Walking

Stephanie is fantastic with dogs of all breeds and sizes. She has the cutest mini golden doodle that she spoils. She has also taken care of my pit/ boxer mix an… (more)

from
$24
per visit
Confirmed availability: Memorial Day
9.
I want to meet your furry friends!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Ethan has three dogs of his own. He’s great with our dogs and our neighbors. He frequently takes dogs for walks around Streeterville and is always at the dog pa… (more)

from
$15
per visit
Calendar Recently Updated
10.
Fun and active dog lover!Near North Side, Chicago, IL, 60611
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 repeat client
5 years of experience

About: Love spending time with dogs of all ages and nothing means more to me than seeing them happy and smiling! I have lots of toys and live right by two d… (more)

from
$20
per visit
Calendar Recently Updated
11.
Experienced dog owner :)Near North Side, Chicago, IL, 60610
Drop-In Visits, Dog Walking

We treat our dog like another kid and it’s hard for us to leave him with just anyone. Kaleigh was AMAZING and we were able to relax and enjoy our weeklong vacat… (more)

from
$20
per visit
Calendar Recently Updated
12.
Work from home/flexible pet sitter!Near North Side, Chicago, IL, 60654
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I've been around dogs for the past 25 years whether it's caring for my own or watching a neighbors dog. Whatever your dog needs will be provided! M… (more)

from
$25
per visit
13.
Put your pet in good handsNear North Side, Chicago, IL, 60654
Drop-In Visits, Dog Walking

We loved Andrew as our sitter for our senior dogs! It's easy to tell he's a true dog lover, and our dogs loved him from the moment they met him. He sent lots of… (more)

from
$25
per visit
Confirmed availability: Memorial Day
14.
Amy 
Verified Enhanced Background Check
Home full-time, active, responsibleNear North Side, Chicago, IL, 60610
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Amy was amazing with our 9 week old puppy. It was a relief that someone so reliable and caring was able to give our puppy some play time during the day! (more)

from
$28
per visit
Calendar Recently Updated
15.
Available to watch your furballNear North Side, Chicago, IL, 60610
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

If you’re looking for a reliable, caring pet sitter, look no further than Steve. Steve is great with my blind 10.5 yo pup. He’s accommodating and so patient wit… (more)

from
$20
per visit
Confirmed availability: Memorial Day
16.
Love your pet as my ownNear North Side, Chicago, IL, 60610
Drop-In Visits, Dog Walking
20 years of experience

About: I grew up in a household with dogs of all sizes. I’ve taken care of my own dogs growing up as well as dogsat/walked friends’ and neighbors’ when they… (more)

from
$15
per visit
Calendar Recently Updated
17.
I give dogs so much attention :)Near North Side, Chicago, IL, 60610
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I took care of others’ dogs all through college. I just moved to Chicago and would be so happy to watch yours for you :) I work remotely Mondays, Tu… (more)

from
$17
per visit
Calendar Recently Updated
18.
Highly available and dependable!Near North Side, Chicago, IL, 60654
Drop-In Visits, Dog Walking

I would highly recommend Teri as a cat sitter. My cat became a little sick while I was away and Teri was able to get her back to good health and kept me updated… (more)

from
$20
per visit
Confirmed availability: Memorial Day
19.
dog mom, swiftie, coffee loverNear North Side, Chicago, IL, 60654
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
2 years of experience

About: I have a beautiful 8 year old golden retriever who is excited to share her home! We have a 3000 sqf dog park in the building and I’ll make sure to gi… (more)

from
$25
per visit
Calendar Recently Updated
Caring and Kind sitterNear North Side, Chicago, IL, 60610
Drop-In Visits, Dog Walking

Christine did a great job looking after my cat while I was away! She was communicative and my cat seemed to love her. I would highly recommend booking Christine… (more)

from
$25
per visit

Dog lovers in Near North Side, Chicago, IL love pet sitters on Rover.com. Over 521 pet owners have reviewed pet sitters on Rover in Near North Side, Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Chicago can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

Rover.com is the simple, savvy way to find and book Near North Side, 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 Near North Side, 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 Near North Side, Chicago, 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: