Pet Sitting & Drop Ins In Uptown 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
Joy D.
1.
Joy 
Verified Enhanced Background Check
Rover 101
Extra caring, loving, soft spokenUptown, Chicago, IL, 60640
Drop-In Visits, Dog Walking

Joy was fantastic! Her communication was excellent and I felt confident that she was taking very good care of my cat. Would definitely recommend her and book he… (more)

from
$35
per visit
Melissa P.
Reliable and professional - always!Uptown, Chicago, IL, 60613
House Sitting, Drop-In Visits, Dog Walking

Melissa was great! She was on time and made sure to get all the info on what Peanut liked and needed during her visit. Melissa was communicative throughout the … (more)

from
$20
per visit
Confirmed availability: Memorial Day
Samaah A.
3.
I have Sa-Much experience!Lincoln Square, Chicago, IL, 60640
Drop-In Visits, Dog Walking

Samaah did a wonderful job looking after my fur baby. She was reliable, and went above and beyond cleaning up after a few pet mishaps. Working with Samaah allow… (more)

from
$20
per visit
Calendar Recently Updated
Rocio S.
4.
Searching for a furry friendUptown, Chicago, IL, 60613
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ro was a great fit for Oreo. She would take care of him during family trips and walk him during the workweek when he needed to go out. Rocio loves dogs. She wou… (more)

from
$17
per visit
Confirmed availability: Memorial Day
Gina C.
5.
Experienced pet care provider :)Uptown, Chicago, IL, 60640
Drop-In Visits, Dog Walking

Gina is amazing! She has a lot of experience with dogs, and she treats my Max and Josie like one of her own! They just love her and look forward to every visit … (more)

from
$15
per visit
Calendar Recently Updated
Missing my dog- ready to meet yoursLake View, Chicago, IL, 60613
Drop-In Visits, Dog Walking

Shelley was great while we were out of town taking care of our Sadie who was only 5 months at the time! She was very attentive and sent lots of pictures. Sadie … (more)

from
$17
per visit
Confirmed availability: Memorial Day
7.
Lifelong animal loverUptown, Chicago, IL, 60640
House Sitting, Drop-In Visits, Dog Walking

Jenie is really great! She has helped take care of my dog many times and takes extra care to follow all instructions given. I would definitely recommend her to … (more)

from
$17
per visit
Calendar Recently Updated
8.
Every dog is my favorite dog.Lake View, Chicago, IL, 60613
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sarah Guinan is an extreme dog and animal lover. She incredibly gentle with all animals and has several years of professional dog walking experience. She treats… (more)

from
$17
per visit
Confirmed availability: Memorial Day
For the Love of DOG!Uptown, Chicago, IL, 60640
Dog Boarding, Drop-In Visits, Dog Walking

Highly recommend Savannah. She went out of her way to take care of our dog over the holidays. She provides fantastic updates and communication, and you can tell… (more)

from
$28
per visit
Confirmed availability: Memorial Day
10.
Pet Sitter AvailableEdgewater, Chicago, IL, 60640
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Carmen is an amazing person who cares for both people and animals alike. She is incredibly loving and caring for her own pup, Stella, and they are two peas in … (more)

from
$17
per visit
Calendar Recently Updated
11.
Active and ready to play and train!Uptown, Chicago, IL, 60640
House Sitting, Drop-In Visits, Dog Walking

Theresa’s cat is very well mannered and friendly to all guests, reflective of her excellent caretaking abilities. I frequently trust Theresa to watch my own dog… (more)

from
$17
per visit
Calendar Recently Updated
12.
I love your pet already! ❤️Lake View, Chicago, IL, 60613
House Sitting, Drop-In Visits, Dog Walking

Cori was extremely communicative and sent the most adorable pictures of my cats at each visit. She played with them a bunch and I know they had some good pets. … (more)

from
$17
per visit
Confirmed availability: Memorial Day
13.
U.S. Secretary of DogsUptown, Chicago, IL, 60640
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I highly recommend Will! He's a very friendly, responsible, and conscientious guy, as well as a genuine dog lover. Rest assured your dog will be in excellent ha… (more)

from
$30
per visit
Calendar Recently Updated
14.
Seasoned Pet Owner & Caregiver!Lake View, Chicago, IL, 60613
Drop-In Visits, Dog Walking

Ellie was absolutely amazing! I was very nervous about leaving my 4 kitties for the first time since I moved to Chicago but Ellie made sure I always had a full … (more)

from
$25
per visit
Confirmed availability: Memorial Day
Dogs are angels !Uptown, Chicago, IL, 60640
House Sitting, Drop-In Visits, Dog Walking

Priscilla is AWESOME with Atom. She's always very attentive and there to play. She always sends updates. She's absolutely the best and Atom adores her. She is d… (more)

from
$20
per visit
Confirmed availability: Memorial Day
16.
Experienced, Passionate Dog LoverUptown, Chicago, IL, 60640
House Sitting, Drop-In Visits, Dog Walking

Nadia did a wonderful job. Pepe sure enjoyed the walks with her. Nadia sent us pictures and highlights of each visit. I highly recommend her services. she is a … (more)

from
$16
per visit
Calendar Recently Updated
17.
Great with animals of all sizesUptown, Chicago, IL, 60640
House Sitting, Drop-In Visits, Dog Walking

Sara was great! Link is a very active dog and isn’t always the easiest to watch after as he is still learning to calm himself at 1 year old. She provided tons… (more)

from
$25
per visit
Calendar Recently Updated
Loving all petsUptown, Chicago, IL, 60640
Drop-In Visits, Dog Walking

Alejandra had great communication with is throughout our experience! We were nervous at first, since we’ve never used this type of all before, but after meeting… (more)

from
$25
per visit
Calendar Recently Updated
19.
Reliable and loving pet sitter!Uptown, Chicago, IL, 60613
Drop-In Visits, Dog Walking

Jayne does such a great job! She is quick to respond and has been able to help out last minute! She sends lots of photos and gives lots of love while we’re alwa… (more)

from
$20
per visit
Calendar Recently Updated
Dogs make the best friends!Uptown, CHICAGO, IL, 60640
Drop-In Visits, Dog Walking

Salvador is a reliable and trustworthy dog sitter. He loves spending time with dogs and often says they are his best friends in life. Salvador knows how to conn… (more)

from
$25
per visit

Pet parents in Uptown, Chicago, IL love dog sitters on Rover.com. 10 owners have reviewed sitters in Uptown, Chicago, giving them an average rating of 4.7/5. 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 Uptown 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 Uptown, 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 Uptown pet sitters and avoid the kennel.

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 Uptown, 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: