House Sitting in 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.
Calendar Recently Updated
Pablo V.
1.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

We left our pup with Pablo at our house for the weekend and he was just incredible. He sent a ton of updates and we just felt so relaxed knowing our dog was in … (more)

from
$52
per night
Calendar Recently Updated
Melissa G.
Undergrad Pet Sitter!Lincoln Park, Chicago, IL, 60614
House Sitting, Drop-In Visits, Dog Walking

My Growlithe was very pleased to meet and spend time with Melissa! I Appreciated the picture updates of their play dates while I was away. Highly recommend her … (more)

from
$38
per night
Confirmed availability: Memorial day
Annie X.
3.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Annie has been a great sitter for my little girl. Always responsive and easy to deal with. You won't regret having Annie to take care of your furbabies (more)

from
$65
per night
Calendar Recently Updated
Ashley O.
4.
I Love PupsWest Town, Chicago, IL, 60622
House Sitting

Ashley took great care of my dog and house over a long weekend. She was very responsive, sent cute pics and left the house in great condition. Will definitely … (more)

from
$40
per night
Calendar Recently Updated
Kat O.
5.
Kat 
Verified Background Check
Quality care for our fur babiesBrighton Park, Chicago, IL, 60632
House Sitting

I highly recommend Kat! She promptly answered all of our questions prior to booking and even came by for a meet and greet to get acquainted with our dog Mo befo… (more)

from
$50
per night
Calendar Recently Updated
6.
Dog lover and always punctual!Loop, Chicago, IL, 60607
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Peyton has been a tremendous help with our dog. She happily walks our Buddy and gives him the attention and exercise he needs. He loves his time with her. (more)

from
$40
per night
7.
Trying to pay for flight schoolNear North Side, Chicago, IL, 60611
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

On time and reliable. No complaints, will book again! (more)

from
$60
per night
Calendar Recently Updated
Pilsen Dog Walker/Cat Sitter!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting

Anthony did a great job house sitting and taking care of our dog while we were away. He sent us daily updates and photos, and we came home to a clean house and … (more)

from
$40
per night
Confirmed availability: Memorial day
9.
Love comes in four legged packages!Near West Side, Chicago, IL, 60661
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Lexi is a wonderful doggy caregiver! I have left my pooch with her a number of times and she is clearly very affectionate and passionate about the animals she c… (more)

from
$42
per night
Confirmed availability: Memorial day
10.
will treat your fur baby like mine!Loop, Chicago, IL, 60606
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I grew up in a household of three dogs. I have such a love for dogs. I have worked with large and small dogs. Currently, I raise a 6 year old papillo… (more)

from
$44
per night
Calendar Recently Updated
Care your baby like my ownNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Chanakarn was great! Super responsive and left me with no concerns while she was watching my pets. I came back to them happy and content. I’d definitely use he… (more)

from
$50
per night
Passionate Pet Care ProviderLoop, Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking

Edie did a great job with playing with Phoenix indoor and walking him outdoors but keeping in mind the hot weather. He gave him medication and fed him as needed… (more)

from
$50
per night
Calendar Recently Updated
13.
Amazing Animal CaregiverLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Emma is a very close friend of mine and she is a great pet owner! She has watched my dog and cats before and I’ve always been more than satisfied with her servi… (more)

from
$80
per night
Calendar Recently Updated
14.
Trustworthy, respectful, and fun!Near South Side, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Nikki was a great sitter for my pup. She was very communicative throughout, sent photos of her with my dog playing in the park, and left the house in better sha… (more)

from
$40
per night
Calendar Recently Updated
15.
Pet lover with park nearby!Lower West Side, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Andrea was everything we could have asked for in a pet sitter. We have one, crazy puppy and two cats. The dog and cats do not get along well and Andrea was able… (more)

from
$49
per night
Confirmed availability: Memorial day
16.
I will love pet like my own :)Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

He was so chilled when I arrived. She was ❤️ (more)

from
$60
per night
17.
There’s no place like home!❤️❤️❤️Lower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Erica did great with our dog! She was very friendly and you can tell that she is a natural animal lover. Erica sent a lot of photos and videos of our dog and he… (more)

from
$30
per night
Confirmed availability: Memorial day
18.
Flexible schedule, adore dogs!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

There are only a handful of people out there that I wholeheartedly trust with my pup - and Angie is one of them. She and I trade off with another friend of our… (more)

from
$40
per night
Calendar Recently Updated
19.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emily is great! Very professional and communicative. A++++ will definitely have her dog sit Niall again ! (more)

from
$34
per night
Confirmed availability: Memorial day
20.
Experienced with dogs and catsLower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

I am so glad that I decided to find a sitter to stay with my dog while we were on vacation and that we chose Dana. Dana is a laid back person which was great to… (more)

from
$34
per night

Check out the House Sitting in your neighborhood:

Rover also offers House Sitting in:


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.