Pet Setting & 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.

Confirmed President's Day Availability
1. Annie

Large or Small - I Love 'em All!

Edgewater, Chicago, IL, 60660

Dog Boarding, Drop-In Visits, Doggy Day Care

5 repeat clients

"We traveled with piece of mind knowing that Annie was taking care of our Cat! She was responsive, timely, and most importantly wonderful to our pet. Cannot t... (more)"

Available this weekend
2. Jacqueline

Dog Lover and Fetch Extraordinaire!

Rogers Park, Chicago, IL, 60626

House Sitting, Drop-In Visits, Dog Walking

"Jackie watched our home and our 8 year old bull terrier mix, Max, for 8 nights & 9 days. our home was well kept and Max had a great time. Santa Jackie brough... (more)"

3. Chloe

Professional dog + cat admirer

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

53 repeat clients

"Chloe did a great job keeping me informed of what was going on with my cat Molly while I was out of town. My cat is very shy and hides for basically everyone... (more)"

Confirmed President's Day Availability
4. Elizabeth

Seeking pups in need of snuggles!

Lake View, Chicago, IL, 60657

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

31 repeat clients

"Elizabeth is awesome!! She took great care of my cat, and was very easy to schedule and communicate with. Also, the pictures from her drop-in were some of th... (more)"

5. Alexandra

Full Time Pet Care Provider

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

23 repeat clients

"Alex was fantastic. I was really nervous about getting a dog walker since I hadn't before and my dogs were not used to anyone else taking care of them. My li... (more)"

6. Anthony

Great with high energy dogs!

Albany Park, Chicago, IL, 60625

House Sitting, Drop-In Visits, Dog Walking

"I hired Anthony to care for my senior dog while I was out of town for 5 nights. He was fantastic! I could tell right away at our "Meet and Greet" that he has... (more)"

Confirmed President's Day Availability
7. Ali

Home Full-Time & LOVE dogs

North Center, Chicago, IL, 60618

House Sitting, Drop-In Visits, Dog Walking

"Ali has such a kind heart and love for all dogs. She is an awesome friend for our family's puppy - he looks out for her each day waiting for his play time. (more)"

8. Amy

Energetic dog and cat buddy

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I wish I could give more stars. Amy is simply the best! Amy stayed in our home and watched our two yellow labs and our two new kittens for a week. They loved... (more)"

9. Holly

Love Dogs More Than (Most) Humans!

Uptown, Chicago, IL, 60640

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Holly has been watching my dog, Penny, for over a year and I cannot recommend her enough. She is responsible, caring, and reliable and I feel 100% comfortabl... (more)"

10. Shamoyita

Dogless dog-lover

Edgewater, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

About: My first experience with dogs (aside from meeting them on the street and playing with friends' dogs) was when we got a family dog when I was 7, and... (more)

11. Emily

Will gladly run with your dog

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

About: Hi, I'm Emily and I've been a lifelong lover of dogs. I've owned multiple dogs throughout the years and grew up around primarily large breed mutts.... (more)

Confirmed President's Day Availability
12. Amber

Energetic, adventurous, dog care

Uptown, Chicago, IL, 60613

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"There is no doubt Amber would excel in performing this service. Amber has not only been around pets her entire life, but also a proud owner of almost every ... (more)"

13. Christina

DogSafe Certified dog lover

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Christina has always been compassionate towards animals. She is very patient and provides the best care possible. She's very understanding and consistent wit... (more)"

14. Natalie

I am a dog's best friend!

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

About: I sincerely believe that best friends come with four paws, fur, and wags their tail when you come home. I have two dogs of my own: a tiny little c... (more)

15. James

Exploring Chicago one pup at a time

Uptown, Chicago, IL, 60640

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"James has been walking my 2 dogs for quite a long time. I trust him with the key to my house, to walk and play with the animals, to give them fresh water, a... (more)"

Available this weekend
16. Ashley

home full time, fenced yard

Lake View, Chicago, IL, 60613

Dog Boarding, Drop-In Visits, Doggy Day Care

"Not only is Ashley an incredible, loving dog mom to her pup Enzo, she is an all around great person. As a former toddler/preschool teacher, Ashley is as resp... (more)"

17. Wynette

The WONDERS of WALKING WITH WYNETTE

Uptown, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

"To fellow animal lovers, It is with pleasure that I am writing to highly recommend Wynette Carmony as a most trusted pet sitter. I have known Wynette f... (more)"

Confirmed President's Day Availability
18. Leah

Loving pet care is here!

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Leah took great care of my cat! She was very friendly and communicative throughout the whole process. (more)"

19. Liz

Depenedable Dog Lover

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Liz was simply awesome! I had great peace of mind knowing that my dog was taken care of while I was at work. Liz sent me updates after each visit and was alw... (more)"

20. Laquita

I really love dogs and enjoy them

Uptown, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

About: As a kid growing up I had a little puppy that I really loved. It ran away and I was so sad. We never found midnight that was her name. So when I ... (more)

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: