House Sitting in Armour Square, Chicago

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

1. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Ashleigh was awesome. It was our first time leaving our pup with a dog sitter so we were naturally a bit concerned as to how our dog would react. We were ver... (more)"

2. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Catherine did an exceptional job dog sitting. I came home to a happy dog and my house in the same condition I left it in. Thank you so much!! (more)"

3. Gabrielle

Pup-loving Medical Student.

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Gabrielle is a hard-worker and a devoted animal lover. She has watched my animals many times and have nothing but positive things to say about Gabrielle! My ... (more)"

4. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Sidney was fantastic, provided me photos daily of Roro, and she was responsive and alerted me to issues. I hope to work with Sidney in the future and would r... (more)"

Available this weekend
5. Julia

Empathetic and dedicated pet lover

West Town, Chicago, IL, 60622

House Sitting, Drop-In Visits, Dog Walking

"Julia is a trust worthy loving person! Her goal is to have her own dog in the near future. She has watched my dog many times, and also has a childhood dog th... (more)"

6. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Penelope has fast become our go-to dog sitter. She has a great, patient, calming approach with dogs that is especially important with little, skittish ones,... (more)"

7. Samantha

Life is ruff! Let me make it easier

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits

4 repeat clients

"Samantha was amazing. We needed someone to sit with Apollo at the last minute and she came through! Apollo loved her and had so much fun playing and sleepin... (more)"

8. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is my first experience with Rover and I couldn't be more pleased. Using Rover came with short notice and I worried that would create a problem. Coll... (more)"

9. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Edilberto was great with Shadow from the first moment. We found a really happy dog when we returned. Edilberto was also really accomodating with out late hou... (more)"

10. Liz

Flat rate for any number of pets!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits

2 repeat clients

"First off, just want to say how much we appreciate Liz being available on such short notice and for a holiday weekend!! My bf and I decided to try and make a... (more)"

11. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

12. Kate

Experienced Dog Lover!!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"I have known Kate for the past 3 years. I have always admired the love and care she gives to her dog, Marshie, and any animal she comes across. Kate is a ver... (more)"

13. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

4 repeat clients

"Allison is hands down the best pet sitter! We had her stay in our home over a long weekend with our two senior pups. She provided excellent communication and... (more)"

14. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Krystina did an awesome job with house sitting our 2 year old mini schnauzer! We had her for multiple days at our house and we couldn't be more satisfied! ... (more)"

15. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

16. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

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

6 repeat clients

About: Ever since I was a child, I have had a passion for dogs and animals of all sorts. Growing up in the Philippines, my relatives found it strange to h... (more)

17. Caitlin

Experience and love combined!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Caitlin is a wonderful person. She is very trustworthy and honest. I have left my dog, Luke, in her care on many occasions. Not only does she watch him and t... (more)"

18. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"Lexy was great! She kept me informed and updated on how Tula was doing. We felt very comfortable leaving Tula with her and trusted Tula would have a great ti... (more)"

19. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

Available this weekend
20. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor has taken care of my blue heeler Winston twice while I've been on trips out of the city. She followed my care instructions excellently and I came hom... (more)"

Experience exceptional service and a personalized match

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Learn About Premier

Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

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.