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House Sitting in West Town, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
1. Cris

mindful & fun + trustworthy & tIdy

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"Cris was EXCELLENT! We have never used a dog walker before or any overnight service for our pets so we were initially worried to try it out. She stood out am... (more)"

2. Alexa

Experienced and Trustworthy

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Alexa stayed with my rambunctious puppy and two cats. I knew when I met her at our meet and greet that she would do a great job! She is super sweet and kind,... (more)"

3. Alyssa

Fetch & long walks to the dog park!

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Alyssa was great! I’ll definitely ask her to come by to walk my pup or watch her and my cats while I’m out of town. She asked lots of good questions during t... (more)"

Available this weekend
4. Clarissa

I won't cancel when it's raining!

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"Our original sitter had an unexpected emergency and wasn't able to watch our two dogs over a holiday weekend. What would have been a nightmare was fixed when... (more)"

5. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel stayed with my two pups for the weekend and she was awesome! I left a ridiculous amount of notes and instructions and she followed everything without a... (more)"

6. Alina

flexible schedule & friendly

West Town, Chicago, IL, 60622

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

"Alina has watched my dog at least 30 times over the last two years. I get a little nervous with how small my Chihuahua is with people watching him, but I kno... (more)"

7. Morgan

I love dogs & dogs love me!

Lower West Side, Chicago, IL, 60608

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

"I would highly recommend Morgan as she has taken care of my dog on several occasions and he just adores her. She treats your dog as if they were her own givi... (more)"

8. Madalyn

Graduate Student Who Loves Dogs

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Madalyn clearly has a special love for dogs. She took great care of Henry while we were away!! She also went out of her way to clean our home which was not i... (more)"

9. Cynthia

Dog & Cat Lover / Maybe Whisperer

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"We love Cynthia!!! She is Dolly’s favorite and always send me pics of snuggles. She’s been so flexible with my new work schedule. I’m not sure what I would d... (more)"

10. Jess

I can bring your dog to work!

Logan Square, Chicago, IL, 60622

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

"If you are looking for someone who is going to spend ACTUAL time with your pup while you are away, look no further! As new doggie parents to one hyper corg... (more)"

11. Angela

Dog-Lover Med Student w/Yard & Love

Logan Square, Chicago, IL, 60647

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

"Angela did a great job with our little ones. It was wonderful to keep them at home to minimize change, especially since we have an older pup. I loved the pho... (more)"

12. Daisy

Lots of experience- Animal Sci Grad

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

"Daisy recently stayed in our home with our two dogs, Chopper and Tiki, while we were away for the weekend. Our dogs are different ages and they have very di... (more)"

13. Hailey

Experienced ASPCA volunteer!!

Loop, Chicago, IL, 60601

House Sitting, Drop-In Visits, Dog Walking

"Hailey did a great job with my Dogs. And even gave special attention to my puppy, because he’s still in the training stages. Thanks for taking my last minute... (more)"

14. Jake

Active Bucktown walker & sitter

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Jakes has stayed with our dogs now three times, and he's been a wonderful find. He did a chemistry check and they immediately felt at ease with him (and my d... (more)"

15. Veronica

Pet Lover with a big heart.

Humboldt Park, Chicago, IL, 60651

House Sitting, Drop-In Visits, Dog Walking

"Great with the dogs and very caring. She even washed the sheets and cleaned up the apartment before leaving! I would definitely recommend, and I'm pretty pro... (more)"

16. Jose

Your dog's favorite sitter

Hermosa, Chicago, IL, 60639

House Sitting, Drop-In Visits

"Jose was great with my pups! I have 2 senior dogs, and one has some minor health issues, so I wanted to be sure they were in good hands while I was out of to... (more)"

17. Rachel

Dog-lover who works from home!

Logan Square, Chicago, IL, 60647

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

"Rachel loves dogs and they "sense it" and respond to her. She is energetic and dogs love that about her too. She is playful just like them and yet she knows... (more)"

18. Robert

All furry friends welcome!

Lake View, Chicago, IL, 60657

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

"Robert was absolutely fantastic in taking care of our pet when we were away. He was very honest and provided regular updates. I would definitely use him in t... (more)"

19. Amanda

Lots of time to walk your fur baby

West Town, Chicago, IL, 60642

House Sitting

"Amanda was amazing! She took such good care of our dog and he absolutely loved her. We got tons of adorable pictures and just could not have asked for a more... (more)"

Confirmed 4th of July Availability
20. Jacob

Full time dog lover

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Jacob was great with our two french bulldogs, one of which can be difficult to take out. He was willing at the last minute to come and stay with them for a ... (more)"


The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving 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 house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. 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 house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.