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 availability
Thanksgiving
1. Jade

Experienced Dog Rescue Worker

Edgewater, Chicago, IL, 60660

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

"I’m hesitant to write this review because I don’t want to share Jade! She is the absolute best! Lionel loves her and she treats him as her own. She’s super r... (more)"

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2. Breanna

100% Love & Attention!!!

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Breanna was so sweet, she sent me adorable pictures of my doggy and even took him for a walk. Thank you Breanna! (more)"

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3. Jenna

Caring, Flexible, and Trustworthy!

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Jenna was fantastic! She sent us photos and a video while she cared for our dogs. We will definitely use her again! (more)"

Confirmed availability
Thanksgiving
4. Jonathon

Cat-dad and personalized dog walker

Lincoln Square, CHICAGO, IL, 60625

Drop-In Visits, Dog Walking

"You can tell how much Jonathon loves animals! He treats them as if they were his own. Jonathan is quiet, but loving, gentle, and energetic with my 3 dogs. Wa... (more)"

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5. Gwenna

Animal lover and puppy trainer

Edgewater, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

"Gwenna took awesome care of my pets and was super nice and flexible! Her updates and pictures made my trip unstressful because I knew they were in good hands... (more)"

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6. Conor

Dogs are a man's best friend

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Not does Conor love dogs, he is also an extremely organized and responsible person. You can rely on his timeliness, attention to detail, and attention to ins... (more)"

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7. Kathleen

Cat owner, dog lover and student

Lincoln Park, Chicago, IL, 60614

Drop-In Visits, Dog Walking

"Kathleen was an amazing sitter for our two cats! Organized, responsive and friendly we were so at ease knowing our pets were under good hands. When we go out... (more)"

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8. Erin

Flexible to fit any needs!

Lake View, Chicago, IL, 60613

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

"I have witnessed Erin interact with and care for a number of different dogs ranging from her small and spunky family dog to our friend's large and sensitive ... (more)"

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9. Elena

Woof approved

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

"Once again Elena took great care of my pups! They are always very happy when I return!! (more)"

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10. Meredith

expert belly rub giver

Lake View, Chicago, IL, 60657

House Sitting, Drop-In Visits, Dog Walking

"Meredith watched my dog for one night and when i picked him up he was happier than he's ever been before. i think she cured him of any depression he had. I r... (more)"

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11. Yelyzaveta

Grad ALL PETS overnight sitter!

Lincoln Square, CHICAGO, IL, 60640

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

"Yelyzaveta was awesome with our two kitties! She made sure to give them both plenty of play and affection while we were gone and made sure that they were wel... (more)"

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12. Spencer

Fresh Air and Fur - The Best Days!!

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Spencer has been my sitter for the past 2 yrs and I have nothing but wonderful things to say about him. My dog Sylvie is a puppy mill rescue who has a huge f... (more)"

Confirmed availability
Thanksgiving
13. Chloe

Professional dog + cat admirer

Uptown, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Chloe was amazing with my pet, we both loved her! She is very informative and attentive. Giving lots of attention and care. We are going to be requesting her... (more)"

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14. Cindy

I’ll run, clean, and feed all dogs!

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"There is nothing Cindy loves more than dogs, and it showed when she babysat for my corgi Rocket. She didn't just walk and feed him, but played with him for h... (more)"

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15. Kaylin

I love caring for animals

Lincoln Square, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

"Kaylin is a meticulous, caring and smart person. She took care of my animals when I had to unexpectedly go out of town. She followed all my detailed instruct... (more)"

16. Sarah

I'll put on my walking boots!

Lake View, chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Highly recommend, would definitely book again (more)"

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17. Nicole

Responsible and friendly!

Lake View, Chicago, IL, 60613

Drop-In Visits, Dog Walking

"It's hard finding a walker for my dog breed because of the stigma associated with them. Nicole was never afraid of my dog and spoiled her with love and affec... (more)"

Confirmed availability
This weekend
18. Mia

Must Love Dogs! (& Cats!)

Edgewater, Chicago, IL, 60640

Drop-In Visits, Dog Walking

"Mia was an excellent person to choose for watching our dogs (we have four). I did not worry at all having them in her care. She kept us updated with each one... (more)"

Confirmed availability
Thanksgiving
19. Chris

Here to care when you're not there

Lake View, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"Chis was great! She was able to sit for us last minute with my dog who has separation anxiety and needs company while we are out. Chris was great with my dog... (more)"

Confirmed availability
Thanksgiving
20. Cera

I'm just a girl who loves dogs.

North Center, Chicago, IL, 60613

House Sitting, Drop-In Visits, Dog Walking

"My blue heeler is an absolute handful. His energy is through the roof and he can be a rather aggressive dog besides. Cera did an excellent job of being s... (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: