House Sitting in Chicago

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Calendar Recently Updated
Sitter Profile Image: Kaitie G.
Verified Enhanced Background Check
Sitter Profile Image: Kaitie G.
Verified Enhanced Background Check

1. Kaitie G.

Star Sitter
Miss Rachel for pets 🐾 she/her(s)
West Town, Chicago, IL, 60622
4.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
8 repeat clients
from
$75
per night

Kaitie took great care of our pup and our home while we were away. She was communicative and shared plenty of photos which put us at ease so we could enjoy our trip. She made sure she had all of the important details about our dog's needs and was very thoughtful about her care. Usually our dog is a bit out of sorts after we've been away. This time he was is normal happy self when we got home which speaks volumes about how much he enjoyed Kaitie's visit :)

Calendar Recently Updated
Sitter Profile Image: Sarah M.
Verified Enhanced Background Check
Sitter Profile Image: Sarah M.
Verified Enhanced Background Check

2. Sarah M.

Star Sitter
We’ll have fun in the paw-ffice!
Chicago, IL, 60651
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
39 reviews
12 repeat clients
from
$57
per night

Sarah did great with our two dogs, including a high anxiety dog who needs medication and extra care on walks. We came home to a spotless apartment and two tired and happy pups.

Calendar Recently Updated
Sitter Profile Image: Megan W.
Verified Enhanced Background Check
Sitter Profile Image: Megan W.
Verified Enhanced Background Check

3. Megan W.

Star Sitter
Megan W. Of Chicago area
West Town, Chicago, IL, 60622
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
60 reviews
16 repeat clients
from
$65
per night

Megan was an excellent sitter for my boys! I was able to leave my 2 boxers home while I travelled for a day long business trip. Megan sent pictures, notes and kept me informed throughout the day. I returned to 2 happy pups and a neat & tidy home. Thank you Megan!

Calendar Recently Updated
Sitter Profile Image: Lindsay J.
Verified Enhanced Background Check
Sitter Profile Image: Lindsay J.
Verified Enhanced Background Check

4. Lindsay J.

Star Sitter
Cat mom and animal lover
Chicago, IL, 60642
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
45 reviews
10 repeat clients
from
$64
per night

Lindsay is great! I travel regularly for work and she is always willing and able to accommodate the early departures and late arrival. She’s very respectful of my place and sends constant updates. My dog loves her and I book her regularly.

Calendar Recently Updated
Sitter Profile Image: Emily N.
Verified Background Check
Sitter Profile Image: Emily N.
Verified Background Check

5. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
118 reviews
36 repeat clients
from
$55
per night

Emily has stayed in my home with my dogs many times now and she has always done an amazing job. Extremely trustworthy, clean, and my dogs are always well taken care of.

Calendar Recently Updated
Sitter Profile Image: Otis B.
Verified Enhanced Background Check
Sitter Profile Image: Otis B.
Verified Enhanced Background Check

6. Otis B.

Dog's Best Friend
Near West Side, Chicago, IL, 60612
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
25 repeat clients
from
$65
per night

I highly recommend Otis as a Rover sitter! He was very punctual and professional during our meet and greet. During his stay in my home, he followed all instructions - including correctly using a type of leash that was new to him - and sent lots of updates and photos. I will definitely book Otis again in the future!

Calendar Recently Updated
Sitter Profile Image: Munder S.
Verified Enhanced Background Check
Sitter Profile Image: Munder S.
Verified Enhanced Background Check

7. Munder S.

Star Sitter
Your pet needs some me time too
West Town, Chicago, IL, 60642
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
129 reviews
47 repeat clients
from
$66
per night

Munder was awesome. Extremely kind, caring and respectful of our home and kitten while we were gone. He sent daily updates and was very communicative. We will definitely have him stay with our kitten again

Calendar Recently Updated
Sitter Profile Image: Saniah I.
Verified Enhanced Background Check
Sitter Profile Image: Saniah I.
Verified Enhanced Background Check

8. Saniah I.

Star Sitter
Saniah: Your pets, my love!
Chicago, IL, 60605
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$50
per night

Arrived in time and take care of my dog perfectly, great communication all the time, definitely recommend her and super happy with the service provided.

Calendar Recently Updated
Sitter Profile Image: Eduardo N.
Verified Enhanced Background Check
Sitter Profile Image: Eduardo N.
Verified Enhanced Background Check

9. Eduardo N.

Loving Care When You’re Not There
Chicago, IL, 60654
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
4 repeat clients
from
$45
per night

Eduardo did a wonderful job watching Obi! Our neighbors commented that it seemed like Obi seemed to be out often with him and they seemed to have fun adventures together. When we came home, he had left the place just as clean as we left it, including washing our sheets for us.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check
Sitter Profile Image: Crystal R.
Verified Enhanced Background Check

10. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
41 repeat clients
from
$65
per night

Crystal did an absolutely wonderful job taking care of our senior dog. She went above and beyond to make sure our Ollie was happy and well taken care of. She sent pictures and updates daily. We plan to use her services again, and highly recommend her!!

Calendar Recently Updated
Sitter Profile Image: Allison J.
Verified Background Check
Sitter Profile Image: Allison J.
Verified Background Check

11. Allison J.

Star Sitter
Previous Veterinary Technician
Near West Side, Chicago, IL, 60608
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
24 repeat clients
from
$80
per night

Allison was fantastic! This is the first time we’ve used Rover for in-house sitting and Allison put our minds at ease right away at our meet & greet. We love that she has extensive experience as a vet tech and felt comfortable leaving both of our dogs (one that can be pretty anxious and take a bit to warm up) in her care. She was flexible, communicative and kept us updated with texts and photos during her stay. Also left the house super clean. Looking forward to booking again!

Calendar Recently Updated
Sitter Profile Image: Taylor M.
Verified Background Check
Sitter Profile Image: Taylor M.
Verified Background Check

12. Taylor M.

Rover 101
Loving, meticulous sitter!
Loop, Chicago, IL, 60001
1.8 mi. away
House Sitting, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
19 reviews
7 repeat clients
from
$50
per night

Taylor is a DREAM dog sitter! She exceeded every single expectation by a landslide and left me with zero worries. Taylor was incredibly communicative, sent tons of sweet updates, and genuinely cared about my pup while I was out of town. I could tell in pictures and videos that my pup was having the best time, getting lots of snuggles, and was calm. She even gave my pup a bath before leaving! Taylor also exceeded expectations by taking excellent care of my apartment. On top of Taylor being completely wonderful, her two pups, Sunny and Leo, were adorable and played really well with my dog. I can’t recommend Taylor enough!

Calendar Recently Updated
Sitter Profile Image: Reshunda B.
Verified Enhanced Background Check
Sitter Profile Image: Reshunda B.
Verified Enhanced Background Check

13. Reshunda B.

Paws-itively
South Lawndale, Chicago, IL, 60608
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$30
per night

Reshunda was prompt and attentive to our care instructions for our special needs pets. She’s a great sitter and I definitely will be booking with her again!

Calendar Recently Updated
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check

14. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$33
per night

Elizabeth was so great! We were able to meet before the house sitting and went over the specifics of my dog. She gave me daily updates and let me know he was doing well which I really appreciated!! I would definitely book again ?

Sitter Profile Image: Deven S.
Verified Enhanced Background Check
Sitter Profile Image: Deven S.
Verified Enhanced Background Check

15. Deven S.

Star Sitter
Nothing better than a happy dog! :)
Near West Side, Chicago, IL, 60607
1.7 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
44 reviews
12 repeat clients
from
$48
per night

Deven is great! He took care of Lilith for more than 3 weeks and kept us updated regularly. He sent photos and FaceTimed us, took her on walks and got her pup cups. Made our time away from our baby better and less worrisome. We definitely recommend Deven! He even stayed late on the last day cause my flight was delayed and I needed him to take care of Lilith a bit more.

Calendar Recently Updated
Sitter Profile Image: Nicole C.
Verified Enhanced Background Check
Sitter Profile Image: Nicole C.
Verified Enhanced Background Check

16. Nicole C.

WFH, responsible, reliable 🧘🏻‍♀️
Near South Side, Chicago, IL, 60616
1.2 mi. away
Boarding, House Sitting
5.0 out of 5 stars
15 reviews
2 repeat clients
from
$72
per night

Nicole was phenomenal with my big, excitable, very opinionated pitbull - Juniper. I was gone for a full week and it was the first time I’d met Nicole. We did a meet and greet and she asked fantastic questions. She checked in a few days before my trip and arrived right on time the day I flew out. Throughout the week I was comforted by little updates and FANTASTIC pictures of Juni (honestly I don’t know how she did it because I haven’t been able to get a good pic out of Juni in months). She asked good questions throughout the week when needed and was super communicative. I got my times mixed up on the Rover app in regards to when I’d be returning and Nicole stopped by the house outside of the agreed upon times to make sure June got her dinner and a final pee. She also changed my bedsheets and folded my laundry??? Truly above and beyond - Juni (and my home and space) were well taken care of. Cannot recommend Nicole enough!

Calendar Recently Updated
Sitter Profile Image: Callie L.
Verified Enhanced Background Check
Sitter Profile Image: Callie L.
Verified Enhanced Background Check

17. Callie L.

I love caring for animals!!
Near West Side, Chicago, IL, 60607
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$50
per night

We were gone a week and knew our Marley and house were in great hands. We have had Callie come see our baby several times before and this time house sit and we don't want to have anyone else take care of her. Our house was well taken care of and my girl is happy, what else could we ask for. I am a hover Mom and Callie just rolled with it and let me know she was doing fine and sent pics and I was able to relax. We can't thank you enough. Callie.

Calendar Recently Updated
Sitter Profile Image: Araceli G.
Verified Background Check
Sitter Profile Image: Araceli G.
Verified Background Check

18. Araceli G.

caring & responsible pet sitter
Near West Side, Chicago, IL, 60607
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
7 repeat clients
from
$50
per night

Araceli is the best!! My dog was recovering from an injury and needed to be watched closely and given medicine while we were gone and she went above and beyond to make sure he was resting and healing and that I felt reassured while being away. She even picked up more medicine when needed. She was responsive and flexible as our travel plans changed. Araceli will take the absolute best care of your pet! She makes a stressful situation much less. Can’t recommend her enough!!

Calendar Recently Updated
Sitter Profile Image: Amanda J.
Verified Enhanced Background Check
Sitter Profile Image: Amanda J.
Verified Enhanced Background Check

19. Amanda J.

Star Sitter
Graduate student who loves animals!
Chicago, IL, 60607
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
11 repeat clients
from
$50
per night

I was going abroad and my friends watching my 7 month old puppy had a 2 day gap. Tyko had only

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Salena V.
Verified Enhanced Background Check
Sitter Profile Image: Salena V.
Verified Enhanced Background Check

20. Salena V.

Will love your babies as my own
Chicago, IL, 60608
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$60
per night

Salena took care of my dog Taffy. It was such a relief to have someone I trusted and he loved when she took care of him and as he aged he let her put meds in his eyes and wiping him down without being a grouchy old dog.

Search Map

Connect anywhere with the Rover app

Chicago House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Chicago are rated on average 4.9 out of 5 stars based on 17,944 reviews.

Check out the House Sitting in your neighborhood:

Rover also offers House Sitting in:

Rover also offers other services in Chicago:


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.

House Sitting