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.

1. Andrea

Student with flexible schedule!

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Andrea was very nice and communicative. She did a great job and left us a detailed report with pictures! (more)"

2. Jacqueline

Dog Lover and Fetch Extraordinaire!

Rogers Park, Chicago, IL, 60626

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jacqueline was easy to communicate with and consistent with her check ins. Being a first time user, I was a little anxious about it but she was quick to put ... (more)"

3. Annie

Large or Small - I Love 'em All!

Edgewater, Chicago, IL, 60660

Drop-In Visits, Dog Walking

7 repeat clients

"Annie was wonderful. She was able to take on watching our cat Freya for the holidays with less than a month's warning. She stopped by each day to take care... (more)"

4. Emma

I love being active with dogs!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Emma was very sweet and responsive! Dexter certainly seemed to enjoy her visits from what I could tell in the pictures she sent me. I will definitely be usin... (more)"

5. Ellie

I only off-fur the best!

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"I can tell Ellie took great care of Lincoln while I was away. I appreciated the check-in updates and pictures during my trip too. Very reliable and attentive... (more)"

6. Georgette

Experienced caretaker for your pet

Rogers Park, Chicago, IL, 60626

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Georgette was wonderful to work with! She took care of my cat while I was out of town & handled all my cat’s quirks with ease. She was reliable and responsiv... (more)"

Confirmed Memorial day Availability
7. Kat

Grad student, full of energy!

Uptown, Chicago, IL, 60613

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"We had such a great experience with Kat, She took wonderful care of our pup Grace. Grace is very shy and takes a little while to open up but by the end of th... (more)"

8. Lanette

Hotel Del Dog!

Rogers Park, Chicago, IL, 60626

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

18 repeat clients

"My kitty needs special care for her condition and age and I was happy to find someone willing to help me out with all of her needs. Lanette did a great job. ... (more)"

9. James

Exploring Chicago one pup at a time

Lake View, Chicago, IL, 60657

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

3 repeat clients

"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)"

10. Amanda

Passionate, Playful and Flexible!

Lake View, Chicago, IL, 60657

Dog Boarding, Drop-In Visits, Dog Walking

12 repeat clients

"Amanda was wonderful! She was extremely accommodating and worked with me about schedules given the short notice of my travel plans. Received tons of pictur... (more)"

11. Michael M. & Brooke

Dog Loving Couple

Lincoln Square, Chicago, IL, 60625

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

3 repeat clients

"Brooke is a loving and caring dog mother! We have sat for her wonderful dog Charlie on multiple occasions, and she has taken care of our dog Milo as well. Sh... (more)"

12. 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)"

13. Monica

Friendly, fun, and loving home

North Center, Chicago, IL, 60613

Dog Boarding, Drop-In Visits, Doggy Day Care

1 repeat client

"Recently, Monica watched our energetic and leash reactive goodledoodle when we traveled for a week. Monica has known Hedwig (our dog) for over two years beca... (more)"

14. Mary

I can't take my cat for walks!

North Center, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"First time using Rover and Mary. Loved the card with pictures and overview of the visit. Mary was also super helpful in the process prior to the visit and a ... (more)"

15. Rachel

Tail-wagging guaranteed!

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

"My name is Amy & I am Rachel's mother. We had dogs all the time when she was growing up. Ever since she was old enough to do so, she has helped take care of ... (more)"

16. Grace

Respectful, cats/dogs/guinea pigs!

Edgewater, Chicago, IL, 60660

House Sitting, Drop-In Visits, Dog Walking

"Grace is one of the best pet sitters I have ever used. She was very attentive the specific needs of my cat and observant of her behavior. Anyone who uses Gr... (more)"

17. Mariah

Purebred dog person

Lincoln Square, Chicago, IL, 60625

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

1 repeat client

"Mariah has been great! She’s been incredibly flexible and is happy to keep you in the loop every visit. Rory loves her new buddy! (more)"

18. Chloe

Professional dog + cat admirer

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

60 repeat clients

"Chloe is 6 stars outta 5!!!! She took care of my 2 cats while I was away and she did a fantastic job. Sent me in update with photos or video everyday. She's ... (more)"

19. Wynette

The WONDERS of WALKING WITH WYNETTE

Uptown, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

20. Chase

Active Pet Owner Home Weekdays

Lake View, Chicago, IL, 60657

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

6 repeat clients

"This was my first time using a dog walking service and I was blown away by how easy it was. Chase arrived promptly on a very chilly winter morning where the ... (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: