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.

Search Results

Calendar Recently Updated
Holly R.
1.
WFH Seasoned SitterWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Holly is really incredible! I have two chihuahuas with very big personalities. They typically are really distrustful of people they don't know, and one of them … (more)

from
$45
per night
Calendar Recently Updated
Pablo V.
2.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo took excellent care of our dog while we were gone. Our dog has lots of energy and anxiety issues and after meeting Pablo and seeing how he responded to ou… (more)

from
$59
per night
Calendar Recently Updated
Sydney R.
3.
Leave your dog in safe hands!Near North Side, Chicago, IL, 60611
House Sitting

Sydney is a good family friend who we have known for years. We have a golden retriever and when we needed someone to watch her during a vacation we felt very co… (more)

from
$60
per night
Calendar Recently Updated
Anna R.
4.
Fall in love with every dog I meet!Near West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking

I have used Anna to watch both of my new puppies while we were away at work. She is absolutely amazing with pets, my dogs just love her! She's very reliable and… (more)

from
$45
per night
Calendar Recently Updated
Kevin J.
5.
West Loop pet lovers! WFHNear West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking
20 years of experience

About: I have always grown up with dogs and loved them. My first dog was a cocker spaniel with lots of energy so I am used to taking multiple walks/playtime… (more)

from
$65
per night
Calendar Recently Updated
6.
Reliable, trustworthy & loving!Bridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Sarai is very sweet and Hugo loves her. She sticks to the schedule and cleans everything up before leaving. I highly recommend her. And… Hugo loves her. (more)

from
$80
per night
Calendar Recently Updated
7.
$20 off for new Rover users!Near West Side, Chicago, IL, 60607
Dog Boarding, House Sitting

Charae was amazing with our needy and demanding French Bulldogs over a four night stay. Charae was a strong communicator, wonderful with the many unique quirks … (more)

from
$150
per night
Calendar Recently Updated
8.
Let me give your pet love and care!Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

I love Riss and her updates while sitting my mini doxies was just what I needed. Its hard as a pet parent to find reliable and trustworthy sitters but I would r… (more)

from
$30
per night
Calendar Recently Updated
9.
I'll love your dog like my own!Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Andrea is super nice and friendly, my German shepherd loves her and is surprisingly super calm after they hang out. I have a pretty busy work schedule and Andie… (more)

from
$75
per night
Calendar Recently Updated
10.
Parent of Jojo the BorgiNear West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We've used Natalie twice now, and both times have been wonderful! Tater - our 7 year old lab - can be a handful, but he is calm and so happy around Natalie. Tat… (more)

from
$95
per night
Calendar Recently Updated
11.
Pet Lover with 10yrs Dog ExperienceLoop, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Aubry was great with our anxious senior dog! She took great care of her, giving her lots of walks and snuggles. She also left our house clean and ready for us t… (more)

from
$65
per night
Calendar Recently Updated
Experienced vet assistant & fosterLower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Stephanie was an awesome house sitter for my energetic pit mix. She was very easy to communicate with and took great care of my dog and apartment. I will defini… (more)

from
$28
per night
Calendar Recently Updated
Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Masheika was great! With manolo she is sweet and patient and loves to cuddle him I think she even spoiled him a little bit with all the cuddles :-) I appreciate… (more)

from
$75
per night
Calendar Recently Updated
14.
Enthusiastic CaretakerDouglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

About: I've taken care of dogs of every kind since I was 6. My parents and family have always had dogs so I have a great affinity towards dogs. I love the c… (more)

from
$75
per night
Calendar Recently Updated
Nurturing Care Giver & Animal LoverLower West Side, CHICAGO, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

About: I am a nurturing, care giver who loves animals! I have been taking care of beloved pets; walking, in home & drop in sitting for 30+ years. I have rai… (more)

from
$100
per night
Calendar Recently Updated
16.
addictive dog lover with open armsDouglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
2 years of experience

About: Although I changed my career goal from being a veterinarian to a food journalist because of my love for food, dogs continue to be my FIRST LOVE! … (more)

from
$40
per night
17.
Dog dad for hireNear West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Evan is the best dog sitter ever! He responds quickly on the app and is organized and efficient with his sitting schedule. He is responsible and trustworthy and… (more)

from
$75
per night
Calendar Recently Updated
18.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emily was absolutely fantastic. She watched our dog for five days and stayed in our apartment- she sent us great updates and did a wonderful job sticking to our… (more)

from
$40
per night
19.
Love and attention for all animalsBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Sujae did a great job carrying for my furry crew when I had to travel! (more)

from
$50
per night
Calendar Recently Updated
20.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits

Annie watched our French Bulldog, Fiona, for 7 days. It was also a holiday weekend which is a big deal. She did a great job with Fiona! She would send pictures … (more)

from
$70
per night

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.