Pet Setting & Drop Ins in Loop, Chicago

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

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

DOGS ARE LIFE

Loop, Chicago, IL, 60607

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

"Nick would be a fantastic and trustworthy dog caregiver. He grew up in house with 2 dogs, so he has experience with dogs. Nick is also straight A responsible... (more)"

Confirmed Holiday Availability
2. Stacy

Only the Best for Your Furry Bffs

Loop, Chicago, IL, 60605

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

About: Hi, I'm a recent college grad living in South Loop with my goldendoodle. My schedule is completely flexible because I work at home most times. I ... (more)

3. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

Confirmed Holiday Availability
4. MP

Cat and dog lover with experience!

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"MP was wonderful and very cooperative. Two of my dogs are elderly and one somewhat neurotic but they were all in great health and happy spirits when I retur... (more)"

Confirmed Holiday Availability
5. Ashland

Not stingy with the belly rubs!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Ashland is amazing with animals. He has always taken care of my "babies" when I go out of town. They get lots of love and attention! I would highly recommen... (more)"

6. Mark

Bark Voyage!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

About: Being away from you is stressful for your dog, so why make it even more stressful by making your furry friend leave home? I am a 26 year old Chic... (more)

7. Megan

Dog Walker Looking for Clients!!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

5 repeat clients

"Megan is AWESOME! Felt so happy receiving so many pictures of my kitties Everyday. Will always look for her to look after them if I'm ever out of town. Thank... (more)"

8. Abby

Experienced Sitter Loves All Pets!

Douglas, Chicago, IL, 60616

Drop-In Visits, Dog Walking

11 repeat clients

"Absolutely excellent! She was available same-day within the hour -- she is awesome. Highly recommended! (more)"

9. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"To whom it may concern, Hailey is a very positive and optimistic person. She is caring and very thoughtful and the positive energy she brings makes her a ... (more)"

Confirmed New Years Availability
10. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Very positive experience with chewy (more)"

Confirmed Holiday Availability
11. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

12. Amanda

Experienced Dog Lover and Owner

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Amanda has watched my dog a couple of times when I have had to go out of town. She has always done an exceptional job watching Teddy! She is loving, warm, ... (more)"

13. Stefani

Dog lover-looking to love your pet

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Stefani is awesome and did a great job! (more)"

14. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"Tatiana did an excellent job of caring for my dog while I was on vacation. Before I left I wanted to see how she and my pup interacted and she was just fanta... (more)"

15. Pamela

Exploring Chi-Town With Dogs in Tow

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Pamela is responsible, caring, and fun! I cannot think of someone more qualified to be a pet sitter and dog walker. Her love of animals and positive energy i... (more)"

16. Sam

Improving lives, one dog at a time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"She's amazing. She had no trouble with my kitten. He isn't used to people but he had no trouble warming up to Sam. She even brought packages inside and manag... (more)"

17. Bernadine

Professional & Caring Dog Sitter

Near North Side, Chicago , IL, 60611

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

About: Hello! My name is Bernadine and I love dogs!! I have always loved animals and grew up with both cats and dogs. I have over 15 years of caring for a... (more)

18. Kellin

Responsible, caring, lover of dogs!

Near North Side, Chicago, IL, 60654

House Sitting, Drop-In Visits, Dog Walking

"Kellin did a great job taking care of our pup for the night and sent us picture updates on his walk. Thanks again! (more)"

19. Mary

Traveling Dog Juggler

Loop, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Mary has watched my dog and helped me walk other dogs on multiple occasions. She is truly a dog lover and I always feel comfortable leaving my dog in her ver... (more)"

20. Shana

Loving. Active. Responsible.

Loop, Chicago, IL, 60605

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

1 repeat client

"Shana was great! Very communicative and responsible in taking care of my elder cat, Phoebe. I would definitely recommend her! (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

When it comes to pet sitting, dog owners in Loop, Chicago, IL love Rover.com. Over 333 owners have reviewed sitters in Loop, Chicago, giving them an average rating of 4.9/5. The cost of pet sitting in Loop 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.

Rover.com is the simple, savvy way to find and book Loop, 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 Loop, 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 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 Loop, 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: