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Pet Setting & Drop Ins in West Town, Chicago

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

Tip: Contact sitters now to confirm availability.
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1. Caroline

Keeping up with dogs at any speed

Lincoln Square, Chicago, IL, 60640

House Sitting, Drop-In Visits, Dog Walking

"Caroline did great with our Jazzy! She was very thorough during the whole process. She made sure to update us with great photos and details of walk/visits a... (more)"

Confirmed availability
4th of July
2. Cris

mindful & fun + trustworthy & tIdy

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"Cris was wonderful with our puppy. She was very diligent about arriving on time and even stayed longer to make sure he did his business. Before she left she ... (more)"

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3. Alyssa

Fetch & long walks to the dog park!

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Alyssa was amazing with our dog, Omar! She went above and beyond to make sure our attention seeking dog got as many pets/walks/snuggles as he wanted. He had ... (more)"

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4. 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)"

Confirmed availability
4th of July
5. Sooze

Flexible schedule; Love fetch

Logan Square, CHICAGO, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"Sooze was really patient with my dog Randy! I asked Sooze for a drop in visit so that I could work on getting Randy used to having strangers in our house. So... (more)"

Confirmed availability
4th of July
6. Katy & Edinson

Caring & Fun Friend to All Animals!

Logan Square, Chicago, IL, 60647

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

"Katy and Edinson have been wonderful. They are timely, professional, and Archie loves them! I know I can count on a quick response to messages and requests. ... (more)"

Confirmed availability
4th of July
7. 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)"

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8. Sarah

Dogs are life

Humboldt Park, Chicago, IL, 60647

Drop-In Visits, Dog Walking

"Sarah treats Lady like family and, we are convinced, that Sarah is Lady's favorite human. Sarah keeps us informed on any detail of Lady's behavior and energy... (more)"

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9. Michaela & Cody

Patient & Fun Dog Owner in Logan Sq

Logan Square, Chicago, IL, 60647

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

"Michaela and Cody are amazing with their pup, Gizmo. They are caring and attentive with Gizmo, and the most loving parents. They always make sure to plan aro... (more)"

10. Samantha

Creative Dog Lover!

North Center, Chicago, IL, 60618

House Sitting, Drop-In Visits, Dog Walking

"Samantha was excellent! She was great at sending us a "rover card" for every stay, played with our dog, took him on walks, and was very professional. Would d... (more)"

Confirmed availability
This weekend
11. Clarissa

I won't cancel when it's raining!

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"We asked Clarissa to check in on our cat when we were out of town for a 10 day vacation. We were flexible on times for her to visit as well as number of dail... (more)"

Confirmed availability
4th of July
12. Robbie

I’ll have more energy than your pup

Near North Side, Chicago, IL, 60610

Drop-In Visits, Dog Walking

"Robert is an incredibly responsible and reliable dog lover. He absolutely adores his 2 rambunctious dogs, and treats all dogs with the same love and care. As... (more)"

13. 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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14. Cynthia

Dog & Cat Lover / Maybe Whisperer

Logan Square, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

"I have had Cynthia cat-sit twice for me now and she has done a fantastic job! She's super friendly and easy to work with and my kitties love her. Definitely ... (more)"

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15. 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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16. 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)

17. 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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18. Rachel

Dog-lover who works from home!

Logan Square, Chicago, IL, 60647

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

"Over the years i have had many dogs. The only person i trust to care for them while i'm out of town or while i'm at work is Rachel. Shes responsible, reliabl... (more)"

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19. 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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20. 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)"

In West Town, Chicago, IL, dog lovers trust Rover.com for their pet sitting needs. Over 520 pet owners have reviewed pet sitters in West Town, Chicago, giving them an average rating of 5.0/5 stars. Booking pet sitting in West Town can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book pet sitting in Chicago on Rover? Check out our average pet sitting rates to get an idea before reaching out and beginning a conversation with a sitter.

Rover.com is the simple, savvy way to find and book West Town, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in West Town, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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 West Town, 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.