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.

Available this weekend
1. Kelly

Mother of two Pitbulls!

Albany Park, Chicago, IL, 60625

Drop-In Visits, Dog Walking

10 repeat clients

"Kelly was awesome!! I would definitely book her again. She did a meet and greet with Paul first. Kelly also stayed a little bit longer because we just got Pa... (more)"

2. Grace

Raised on a farm with 6+ dogs

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Grace had the ability to "give it her all". She absolutely loves animals and is willing to go the extra mile to ensure the animals are taken care of. I trust... (more)"

3. Michelle

I'll love your pup!

Lake View, Chicago, IL, 60613

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

About: My name is Michelle. I'm a dog lover who will take care of your dog and respect your home! I'm a hairstylist and make my own schedule so I have a l... (more)

Available this weekend
4. Gabby

Ready to make your best friend mine

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

About: Working with animals has always been a part of my life. From raising two dogs on my own to walking dogs for apartment buildings, ive become a dog e... (more)

5. Alexa

Treating your pup as my own!

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Alexa was very responsive via email/text and made our trip worry-free as far as our pup was concerned. Plus, Jazzy looked very happy in all of the daily pho... (more)"

6. Haley

Dogs are my favorite animal!

Edgewater, Chicago, IL, 60640

House Sitting, Drop-In Visits

2 repeat clients

"Haley was great with our mini-schnauzer when she filled in when our regular sitter was out. I would recommend her to others and she takes great care. (more)"

7. Carrie

Home full-time; fenced yard; runner

Rogers Park, Chicago, IL, 60626

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

"Carrie is great with dogs. She grew up with dogs and loves hanging out with dogs when they are around. She actually taught me a lot about dog leases. I wo... (more)"

Available this weekend
8. Barbie

HOME OFTEN- ENERGETIC

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Barbie was great with our pup! She's very reliable and dependable and our pup loved her. She is super nice! I would definitely recommend her for dog walking. (more)"

9. Maie

Trustworthy friend for your pup!

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"She was fantastic and got along really well with my cat! I will be using again in the future! (more)"

10. Andrew

I'll run with your dog!

Lake View, Chicago, IL, 60613

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

1 repeat client

"Andrew is a kind, compassionate and dependable person. He loves all animals, especially dogs. Andrew loves the out doors and so dog walking is a natural fit... (more)"

11. Annie

Energetic, responsible dog lover!

Lincoln Park, Chicago, IL, 60614

Drop-In Visits, Dog Walking

1 repeat client

"Annie was such a champ and wonderful caregiver. She swept in last minute and met me the night before I needed her, showed up promptly, went above and beyond ... (more)"

Available this weekend
12. Rebekah

Close to Lake MI & LP

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Bekah is incredibly responsible and very trustworthy. We share a mutual high-profiled friend and she has been entrusted in the past to dog sit for that indiv... (more)"

13. Sabrina

Your Dog's Best Friend

North Side, Chicago, IL, 60613

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

11 repeat clients

About: To say I love dogs is an understatement! I have grown up with dogs my entire life and have experience pet sitting dogs as small as a 12 year old, 2... (more)

Available this weekend
14. Ashlyn

Home full time - flexible

North Center, Chicago, IL, 60613

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

About: I am an absolute dog lover. I grew up with dogs and was the primary care-giver/trainer in the family. I am now a dog mom to a sweet beagle mix who ... (more)

15. Parker

Ill treat your pet like its my own

Lake View, Chicago, IL, 60613

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

3 repeat clients

"Parker is a super responsible and dependable animal lover. She will treat your dog like her very own. She will be on time and will always follow through. Sh... (more)"

16. Rebecca

Bubbly animal lover/college student

Uptown, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rebecca has significant experience caring for dogs. I can always see how much she loves animals, and she would be an excellent addition to Rover! (more)"

17. Olivia

Me + Your Pets = BFFs!

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Olivia is trustworthy and reliable. On multiple occasions I've had to go on work trips for conferences and have to leave my pugs and cats at home alone. Ever... (more)"

18. Christina

I like Big Mutts and I cannot lie!

Edgewater, Chicago, IL, 60660

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

5 repeat clients

"Christina watched my dog Chloe for a week while I was out of town. I am always worried when leaving her as she is moody. However Christina made me feel so co... (more)"

19. Alexandria

Pup Adventures with Alex

North Side, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"We could not be happier finding Alex to watch our sweet Bennie over the weekend. On Thursday morning I left a request for Alex to see if she was available th... (more)"

20. Eliana

Dream big and love dogs!

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Eliana is my Step daughter. She help me train and raise our German Shepard. She has excellent knowledge of dogs and how to read their temperament. Her pati... (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: