Pet Setting & Drop Ins In Near South Side Chicago

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

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

2. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

3. Dana

Mother of Dogs for Decades!

West Town, Chicago , IL, 60642

Drop-In Visits, Dog Walking

1 repeat client

"Dana was great! Lots of detailed updates and pics, which I love when I'm away. I definately recommend her! (more)"

4. Sarah

Lots of experience!

Near North Side, Chicago, IL, 60611

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

About: I absolutely love working with dogs! I have about 10 years of dog sitting and dog walking experience. I have also fostered and helped train a servi... (more)

5. Miki

Active dog lover!

Near West Side, Chicago, IL, 60661

House Sitting, Drop-In Visits, Dog Walking

About: I have been caring for my family dogs and have been pet sitting all my life! I currently have a 20 lb cockapoo Cooper who is very active as well. U... (more)

6. Brittany

Grad student dog lover

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits, Dog Walking

About: Hi I'm Brittany! I'm a Physical Therapy student and life long dog lover. I can come to you to play with your dog, care and feed, and take him/her o... (more)

Available this weekend
7. Caraline

Experienced & Certified Pet Sitter

Loop, Chicago, IL, 60606

Drop-In Visits, Dog Walking

3 repeat clients

"Caraline is the ultimate professional and takes such good care of your pet. Kofi loves her to pieces. She is trained in many different pet care skills and is... (more)"

8. Kelly

Running through the summer!

Near North Side, Chicago, IL, 60611

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

3 repeat clients

"Kelly was great! She watched my Australian shepherd for two weeks! I would recommend her to watch my dog any day! I received many photo updates throughout th... (more)"

9. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

10. Nicole

The ultimate dog lover!

Near North Side, Chicago, IL, 60611

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

1 repeat client

"Hello pet parents, I was the Mom to a wonderful Beagle that brought so much joy to our lives until the very day he passed away from old age. Nicole C would ... (more)"

11. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

12. Ashley

Flexible schedule; long walks

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

1 repeat client

"Ashley was absolutely wonderful! She was very thorough in describing her visits with my dog & I almost felt like I was home with them. I returned home from m... (more)"

Available this weekend
13. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Megan did a great job with my cat Helice when I was out of town for one week. She checked in every day by texting me and sending me photos. When I came back ... (more)"

14. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

1 repeat client

"Alex took great care of my cat when I was traveling! She sent pics and kept me updated during my trip. I would recommend Alex to anyone who needs a responsib... (more)"

15. Steven

Trained, reliable dog lover!

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Steven watched our dog for the better part of two weeks while we were on vacation. He gave us a lot of pictures and written updates on our our dog Sydney was... (more)"

16. Margaret

Dog lover with vast experience!

Near West Side, Chicago, IL, 60661

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

1 repeat client

"The best (more)"

17. Rebecca

Home full-time - Love being outside

Near South Side, Chicago, IL, 60616

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

"I have never met anyone that loves and cares for dogs as much as Rebecca does! I have had her walk/watch my dogs many times and she is so good with them. A... (more)"

Available this weekend
18. Betsy

Loop apartment w/ outdoor dog run!

Loop, Chicago, IL, 60601

Dog Boarding, Drop-In Visits, Dog Walking

"Betsy is a loving, caring dog owner for her Bulldog Mac. Not only is she great at caring for her fur-child, but she has watched our French Bulldog who has so... (more)"

19. 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)"

20. Anna

Dog Lover with a Boston Puppy

Loop, Chicago, IL, 60601

House Sitting, Drop-In Visits, Dog Walking

About: Since I have an energetic 10 months old Boston Terrier puppy I am used to taking at least an hour walk everyday. I usually take him for a walk, or ... (more)

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Learn About Premier

Dog owners in Near South Side, Chicago, IL love booking pet sitting with sitters on Rover.com. Over 7,915 pet owners have reviewed pet sitters in Chicago, giving them an average rating of 4.9/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Near South Side, Chicago.

Rover.com is the simple, savvy way to find and book Near South Side, 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 Near South Side, 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 Near South Side, Chicago, 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: