House Sitting in Armour Square, Chicago

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

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

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I grew up with two dogs, a Doberman and a mixed breed, and I am very comfortable and experienced around all types of dogs and all types of dog pers... (more)

Confirmed New Years Availability
2. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Cherise is a great dog/house sitter. Our dog Bentley is shy and timid but he took a liking to at their first meeting. Cherise was also very flexible to accom... (more)"

Available this weekend
3. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

4. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Krystina stayed at our apartment over the weekend to take care of our two dogs. She did a wonderful job with the boys in our home. We were very happy and sat... (more)"

5. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

6. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Hailey was great! I trusted leaving Tula with her for a few days over the holiday weekend. She gave me updates, sent me a pic, and my house looked untouched... (more)"

7. Cristina

Ideal human:Active,fun, friendly.

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Cristina was great! Prompt communication, flexibility in her schedule, and a love for my puppy - what more could I ask for. She sent a number of pictures t... (more)"

8. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was fantastic and was my first sitter via Rover. She took a last minute job with me (same day for a 3 day long overnight) and was great! I was comfortab... (more)"

9. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Catherine has been an animal lover since I've known her. She volunteered at a dog rescue shelter while away at college and continues to volunteer with a Chic... (more)"

10. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

11. Eliana

I am friendly, punctual, and ready!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana took good care of our dog and cat while she stayed in our home for an extended week trip. She provided timely updates when I inquired about them throu... (more)"

12. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Christina is terrific! She has become our regular dog-sitter when we are away for the night. She shows up on time, confirms everything upon arrival, sends no... (more)"

Confirmed Holiday Availability
13. Jordin

Caring, Warm-hearted and Active

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Jordin is always great - makes traveling easy. She is on time, provides pictures and updates, and is quick to respond. I absolutely recommend her. (more)"

14. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is an angel! She loves my sweet baby Ray like one of her own. Sarah has watched Ray on multiple occasions. During their time together she often takes h... (more)"

15. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

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

1 repeat client

"Erin is an excellent sitter! She's very clearly an animal lover, and I feel completely at peace when I leave Rumi with her. (more)"

16. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Thank you Emily for taking care of Cali while we were gone! Emily was flexible with the hours we needed and gave us an update or two each day. We came home t... (more)"

Confirmed Holiday Availability
17. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

18. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

2 repeat clients

"Alexis took great care of my golden retriever puppy and adult Chihuahua! Her response time was very fast and she was flexible and able to stay at my home to ... (more)"

19. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Collin Sanderson is s very responsible dependable young man. He is also very loving, sincere and compassionate in every aspect of his life. I would trust him... (more)"

20. Kayla

For the Love of Dogs!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Kayla is very sweet and my dog and cat loves her. I received pictures and details of each day. It was great seeing the details of their days. (more)"

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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.

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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.