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Pet Setting & Drop Ins In Near West Side Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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1. Kelsey

Cat and dog lover!

West Town, Chicago, IL, 60622

Drop-In Visits, Dog Walking

"My parents are veterinarians, I have one cat who is my WORLD, and there’s no reason to look at any more pet sitter profiles—choose Kelsey! She did a PERFECT... (more)"

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2. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Karolina is the best! She house sitted for a long weekend and I'm pretty sure our pup was sad we were back and she had to leave. She walked him a LOT and sen... (more)"

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3. Alexa

Quality care for your fur kids

Near North Side, Chicago, IL, 60654

House Sitting, Drop-In Visits, Dog Walking

"Alexa was amazing. This was my first time using Rover and am sold. Alexa provided great updates with each visit and made me feel good that my pet was being ... (more)"

Confirmed availability
4th of July
4. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

"Megan responded quickly and was very easy to coordinate with about the cat sitting I needed. She took lovely photos and my cats were very relaxed and comfort... (more)"

Confirmed availability
4th of July
5. Jacob

Full time dog lover

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Jacob is awesome! I left my dog with a friend, who informed me last minute that they would be home some hours later than expected and wanted to know if I cou... (more)"

6. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Payal was great with our cat - gave lots of attention, was prompt woh texts and photos, and was always sure to let us know our little girl was doing well! (more)"

7. Alina

flexible schedule & friendly

West Town, Chicago, IL, 60622

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

"Alina was the best! I needed someone to drop in on my recent rescue, Daisy, while I was working long hours. It was such a relief to get so many cute photos o... (more)"

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8. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"She was very timely and sent me pictures of the dog which eased my mind while I was gone! I will definitely rebook Ivana! (more)"

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9. Sarah

Huge Dog Lover Home Full-Time :)!!!

West Town, Chicago, IL, 60612

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

"Sarah was great with our puppy Emmie! She came by twice to let Emmie out during the day and was very prompt, and kept us very informed how our puppy did. Tha... (more)"

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10. Lauren

Any and all dogs!

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Lauren is very professional and takes great care of our dog. She is patient with our puppy and we greatly appreciate it. I'm so glad to have her as a trusted... (more)"

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11. Brian

Brian and Sheila's Humboldt Bark

West Town, Chicago, IL, 60622

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

About: Hi our names are Brian and Sheila! We have over 15 years of experience with all types of dogs and would love to meet your cuddly bundle of happines... (more)

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12. Sophia

Near lots of dog parks!

Lower West Side, Chicago, IL, 60608

Drop-In Visits, Dog Walking

"Sophia was awesome! She made going out of town for a long weekend stress free. She watched our dog for four days, and always made sure to send us updates and... (more)"

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13. Claire

Always room in my heart for a pup

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Claire is a responsible, reliable, and energetic dog-lover! She treats all pets like they were her own. You’d be lucky to have her as a dog sitter! (more)"

14. Emily

Student with a love for dogs

Near North Side, Chicago, IL, 60610

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

"Emily was incredible! She was punctual, caring, and my dog absolutely loved her. She wrote detailed notes and took super high quality pictures. It was such a... (more)"

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15. Ashleigh

DOG LOVING STUDENT IN CHICAGO

West Town, Chicago, IL, 60642

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

"Our dog Babs had emergency surgery over the Christmas holiday, and we needed someone last minute to look after her while at work and give her some medicine d... (more)"

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16. Madalyn

Graduate Student Who Loves Dogs

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Maddie has cat sat for me several times in the past and has always been super helpful/flexible. She gave me updates, sent pics, and followed my cats normal r... (more)"

17. Billy

Fenced yard with Puppy Pool!

West Town, Chicago, IL, 60622

Drop-In Visits, Doggy Day Care, Dog Walking

"My dog Chicken is a 2 year old hound mix who loves to play and get pets. I trust Billy with Chicken more than anyone else. I lived with Billy when he first... (more)"

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18. Todd

Home full-time - will love your pet

West Town, Chicago, IL, 60622

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

"Todd grew up with a dog and had daily expectations to feed and care for his dog. Todd had cared for my dogs under the worst Chicago weather conditions. He is... (more)"

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19. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel has taken care of a number of our family dogs on multiple occasions. Her gentle, patient manner have been much appreciated due to our dogs' anxious nat... (more)"

Confirmed availability
4th of July
20. Stephanie

Teacher w/ Flexible Summer Hours

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

"Stephanie was a great sitter! She followed my instructions to a tee and checked in often. (more)"

When it comes to pet sitting, dog owners in Near West Side, Chicago, IL love Rover.com. Over 09 owners have reviewed sitters in Near West Side, Chicago, giving them an average rating of 5.0/5. The cost of pet sitting in Near West Side may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Near West Side, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Near West Side, Chicago who can provide the care your pet needs, when they need it.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Near West Side, 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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.