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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Mirella

Dog & Cat Lover - Quality Care!

Avondale, Chicago, IL, 60618

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Mirella has been wonderful. So kind, patient, communicative and attentive to my needs. I look forward to working with her again! (more)"

2. MC

Canine Loving Law-Student!

Edgewater, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"MC is super responsive, proactive, and generally awesome. She always communicates clearly and takes the best photos. Thank you! (more)"

3. Anna

I just love dogs

Lincoln Square, Chicago, IL, 60625

House Sitting, Drop-In Visits, Dog Walking

"Anna is a strong animal lover with a great history with dogs. She grew up with dogs and is a fantastic mother to her current dog Harvey, whom she rescued thr... (more)"

Confirmed New Years Availability
4. Brittany

Professional Dog Bed

Irving Park, Chicago, IL, 60618

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

29 repeat clients

"Brittany was great! She came twice in one day to take our pup for a walk and we loved seeing the photos and updates. We will definitely use her again! (more)"

5. Hayley

Reliable, Safe, Caring & Energetic!

Lake View, Chicago, IL, 60657

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

"Hayley is so clearly a dog-lover and a wonderful one at that. She dropped in on my 11- week old golden retriever puppy, Kevin, and stuck with him longer than... (more)"

Confirmed New Years Availability
6. Michelle

Puppy loving psychology student

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

About: Hi! I'm Michelle, and I'd love to be your dog sitter! I've grown up with dogs (my first dog was a bichon that my four-year-old self ingeniously nam... (more)

Confirmed Christmas Availability
7. David

Passionate Pet Care Provider

Uptown, Chicago, IL, 60613

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

1 repeat client

"David was amazing and really helped me out yesterday. My flight was delayed and my cats needed to be fed, so I contacted David last minute to see if he coul... (more)"

8. Devin

Social worker and pup lover

Lake View, Chicago , IL, 60613

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"DEVIN is an absolute Pet Favorite! Bentley and Jag are ALWAYS happy to see her. Super dependable and treats my dogs like they are my children (which of cou... (more)"

9. Mark

Bark Voyage!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

About: Being away from you is stressful for your dog, so why make it even more stressful by making your furry friend leave home? I am a 26 year old Chic... (more)

10. Daisy

Lots of experience- Animal Sci Grad

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

1 repeat client

"Daisy is great! She took care of my cat and sent daily updates. (more)"

11. Cooper

WFH & looking for man's best friend

Lake View, Chicago, IL, 60657

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

"Cooper was great! He was super understanding and flexible when it came to my dogs needs. He can be very picky with whom he gets along with and Cooper made hi... (more)"

12. Brenna

Fun, Caring, the Best Puppy Sitter

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Brenna is awesome! She posted me photos of my kitty and the kitty took a liking to her too. I would love to get her services again when I go on a vacation. (more)"

Confirmed Holiday Availability
13. William

Affordable, Reliable, Personal.

Lake View, chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I started working for a small company in Lake View shortly after I moved to Chicago. When they decided to stop offering their dog walking service, ... (more)

14. Sarah

Dog Lover with Flexible Schedule

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is reliable and speedy to answer. I never have to worry about my dog when she's taking care of him. (more)"

Confirmed Holiday Availability
15. Chloe

Professional dog admirer

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Chloe was dependable, trustworthy, flexible and passionate about taking good care of our little dog Sadie. She communicated with us often on Sadie's well-be... (more)"

16. Tara

New city, new fuzzy friends.

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Tara is great! She cared not only for our dog but also gave our cat some love! She came during World Series craziness and we really appreciated that! Tara ... (more)"

17. Nicholas

Barks and Recreation

Rogers Park, Chicago, IL, 60626

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

1 repeat client

"Nick absolutely loves dogs! He grew up in a dog household, so not only does he love them, he also has a very keen sense of how to care for and train dogs to ... (more)"

Confirmed Holiday Availability
18. Sundas

I want to make furry friends! <3 :)

Uptown, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Sundas took excellent care of our babies and was great at keeping us updated. Highly recommended! (more)"

19. Erin

Work from home dog lover & spoiler

Uptown, Chicago, IL, 60613

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

9 repeat clients

"I couldn't possibly ask for a better dog sitter than Erin. I have left my dog, Callie, with her on numerous occasions and it always brought me a sense of eas... (more)"

20. Mollie

I love dogs more than everyone else

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Not only did I own a rowdy black lab of my own for 8 years, I also had a part time job in college that included house sitting and pet care for two ... (more)

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

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: