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.

1. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 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)"

2. Madalyn

Graduate Student Who Loves Dogs

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"My 110lb Doberman Poodle mix ADORES Madalyn! He is so happy to see her. Highly suggest introducing your furry child to their soon to be favorite human! Mada... (more)"

3. Corbin

A happy dog, makes a happy world!

West Town, Chicago, IL, 60642

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

1 repeat client

"Corbin is a trustworthy and caring human that your pup will love! I'm so lucky to have him in my and my pup's life. He is my go-to whenever I need anyone to ... (more)"

4. Laura

Capable, Caring Dog Lover

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Laura is friendly, kind and very experienced with dogs. She is so thoughtful around making each individual dog feel comfortable and happy. We met her a few w... (more)"

5. An

Pets deserve LOVE - they’re family!

Near North Side, Chicago, IL, 60611

Drop-In Visits, Dog Walking

3 repeat clients

"An has been a lifesaver as I take on a new puppy. We have great communication which is super helpful as I try to get my puppy into a schedule. I trust An com... (more)"

6. Holly

Graduate Student and Dog Lover!

Near North Side, Chicago, IL, 60610

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

7 repeat clients

"Holly was fantastic with my pup Minnie and provided great summaries about her check-ins. Minnie is pretty stubborn pup, so I really appreciate Holly's patien... (more)"

7. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 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)"

Confirmed Memorial day Availability
8. May

Always home cuddling :)

Near North Side, CHICAGO, IL, 60611

Dog Boarding, Drop-In Visits, Doggy Day Care

"May is a very kind and caring person. She has a dog and she put much effort to take care her dog. Since we are neighbors, she sometimes help me take care my ... (more)"

Confirmed Memorial day Availability
9. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

43 repeat clients

"Me and my dogs loved Megan! She was very responsive, flexible, and gave great updates with pictures. We had her come three times a day while we were gone for... (more)"

10. Sara

Always home to tend to your doggy!

Lower West Side, Chicago IL, IL, 60608

Dog Boarding, Drop-In Visits, Dog Walking

"Sara is one of the most responsibly caretakers for dogs that I know, and her genuine love of dogs specifically makes her an excellent candidate as a dog sitt... (more)"

11. Tori

Will love on and exercise your dog

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

"My two Golden Retrievers absolutely LOVE it when Tori spends time with them!!! She is so loving and affectionate with them! They can be a lot to handle on wa... (more)"

12. Alexis

Your dog will miss me when I'm gone

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"I have known Alexis since she was 9 yrs old!! She was my neighbor for 10 yrs!! She always had a houseful of animals!! She would walk her 3 little dogs around... (more)"

13. Austin

Your Dog’s Other Best Friend

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

"Austin was amazing with my dogs and they loved him. He makes sure they were safe and played with as much as possible. He also loves them and treats them lik... (more)"

Confirmed Memorial day Availability
14. Jennifer

I brush my dogs teeth everyday!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Jennifer made me feel comfortable booking on Rover for the first time. We love her!! (more)"

15. Kelyn

The Dawg Whisperer!

Near North Side, Chicago, IL, 60611

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

"Kelyn is an amazing dog-sitter. He's caring, responsible, and always very attentive to pets. He thoroughly enjoyed playing with my dog and made sure he got h... (more)"

16. Christie

Responsible dog handler

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"She has watched all 3 of my dogs at once! I completely trust her with them! I know that they are a hassle but she makes taking care of them look easy! She cr... (more)"

Confirmed Memorial day Availability
17. Ashley

You'll get ALL the puppy pics! :)

West Town, Chicago, IL, 60642

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

3 repeat clients

"This was my first time using Rover and Ashley exceeded all my expectations. I have 2 very social cats so just leaving food and water doesn’t quite cut it. As... (more)"

18. Maddi

Love to walk, watch and run dogs!

Near North Side, Chicago, IL, 60610

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

"Maddi has grown up with dogs all her life. she has experience with all size breeds and is a huge dog lover! Maddi understands what they need and can adapt ... (more)"

19. Laura

Exercise and TLC - Dog Lover!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Laura did such a great job taking Daisy out. It looks like they both had loads of fun from the photos that she sent. She was incredibly reliable with respond... (more)"

Confirmed Memorial day Availability
20. Ashley

Compassionate & Reliable Walker

Near North Side, Chicago, IL, 60610

Drop-In Visits, Dog Walking

4 repeat clients

"Ashley was great! My dog Parker really took to her and she sent cute pics and detailed updates. Highly recommend and will use again! (more)"

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:

* 5 FREE WALKS codes may be used only by new On-demand dog walking users.