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
$65
per night

Kaitie was amazing with Sasha! I had lots of picture updates and great communication. Sasha clearly had a great time and enjoyed all her walks. Kaitie left the house cleaner than when she showed up and was a really great guest. I highly recommend her! Thank you!

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

2. 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

She did a great job and obviously handled our nervous/leash aggressive dog super well! She was really communicative and met all of (our and) Annie's numerous needs!

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

3. 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 was a rock star sitter to my pup. She was responsive, confirmed she arrived, sent timely updates and pics! When I first met her she immediately took notes and was focused on taking in the details to do a good job. I’ll hire her again when the need arrives.

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

4. 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
54 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: 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 was professional and communicative and took very good care of our senior cat and dog. Emily shared many updates and photos and left our apartment the way she found it. I would recommend this sitter!

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

6. 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 kept us updated with cute photos and was so great. Our vacation was better because we had no worries about our pets with Munder taking care of them!

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

7. 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

Saniah is great! She was on time and clearly showed that she cares for animals, asking about our dog’s favorite toys and treats. I felt entirely comfortable leaving our dog with her in our home and we will be using her again!

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

8. 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 is awesome. This was our second time having her watch our two pups so she knew their routine, was great with communication and keeping us updated with messages and pics while we were gone. Once again left the house cleaner than when we left. She’s great- thanks again Allison!

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

9. Ann Marie M.

Star Sitter
In a bind? I’d love to help!
West Town, Chicago, IL, 60482
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
78 reviews
29 repeat clients
from
$90
per night

Ann Marie was great with our boys. She’s communicative, caring, left our house in perfect condition, and followed our instructions! Our boys were so happy under her care! Would 100% recommend and book again. Thank you Ann Marie!

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

10. 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

I had a wonderful experience with Taylor. During this hot season when all local boarding facilities were full, I decided to try the Rover app for the first time to book a dog house-sitting service. And I must say, I am beyond satisfied with Taylor's exceptional service. Taylor not only took great care of Max, but she also kept our house clean and tidy throughout her stay. It was a relief to know that Max had some company during the day as Taylor brought her own adorable dogs, Leo and Sunnie, to our home. Max absolutely loved playing with dogs smaller than him, and the videos and photos Taylor sent us of their playtime brought a smile to our faces. Taylor's regular updates were a huge comfort, as she shared detailed summaries of Max's daily activities, including potty breaks, meals, and even poop schedules. It was evident that Max was happy and thoroughly enjoying his time with Taylor. This first experience using Rover exceeded my expectations, thanks to Taylor's care and dedication. I've decided to forgo external boarding facilities and will confidently use Rover for any future puppy services. Without a doubt, I will be reaching out to Taylor again the next time we travel. Her professionalism, attentiveness, and genuine love for animals have left a lasting impression, and I can't thank her enough for taking such great care of Max.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check
Sitter Profile Image: Elizabeth D.
Verified Enhanced Background Check

11. 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

They were AWESOME! Immediately we hit it off talking about our mutual interests. My dog gets a bit hyper but Levi was able to demonstrate techniques to calm him down and quickly. Once I left they sent me regular updates and I never had to worry about whether or not my kitten and dog were in good hands. I really appreciate the time and effort they put into making sure I was updated. I’ve never used Rover but I definitely will again. I also will definitely be using Levi. Thank you so much for everything!

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

12. 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 was fantastic. She took such great care of Sophie while my wife and I were out of town Araceli provided us with daily updates and texted us with any questions she had. Araceli stayed at our house and when we returned everything was as clean or cleaner then we left it. I would highly recommend Araceli.

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

13. 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.

Sitter Profile Image: Amanda B.
Verified Enhanced Background Check
Sitter Profile Image: Amanda B.
Verified Enhanced Background Check

14. Amanda B.

Headline incomplete
Loop, Chicago, IL, 60605
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
4 repeat clients
from
$35
per night

Amanda took such good care of my kitties and was very communicative! I got updates daily of how they were doing. My apartment was tidy when I got back. Great experience!

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

15. 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 went above and beyond what we could've asked for from a sitter. She stayed at our place for a week and looked after our two boys. Our youngest Vinny had started to have a little bit of diarrhea before we left for vacation, but we thought it would pass with some water and a few extra potty breaks. A few days into her stay, it was apparent it was getting worse, so we got in contact with our vet and arranged for testing and meds. Nicole handled everything with the vet and the boys so fast, and was so communicative and organized. And I know Vinny - he's a handful on his own, but with a tummy ache, you need to keep your eyes on him 24/7, and she did just that. I'm so thankful to have had someone take care of him the way I would. We also have this little ritual we keep with our pup Rusty's memorial (he passed a year ago). She kept up our little routine and gave us updates on him too :) We just off-handedly told her it was a thing we do, and the fact that she kept it up meant so much. I could ramble on forever! Bottom line, Nicole is an exceptional sitter/person and I would 10000% trust her with my boys again.

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

16. 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

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
22 reviews
5 repeat clients
from
$50
per night

Callie was extremely communicative since day 1 of reaching out to her, we did a meet and greet and the dogs seemed instantly bonded with her and she asked a bunch of questions to really get to know their schedules and personalities. During our stay she provided us with updates and pictures and when we came home the house was spotless and the dogs were so happy. She is an extraordinary caretaker and even more talented artist! I’m so glad we went this route instead of the dog hotel this time around because my dogs are so much happier and healthier because of Callie. Anytime I had a special request she was there to help me out. Thank you so much.

Calendar Recently Updated
Sitter Profile Image: Marlena H.
Verified Enhanced Background Check
Sitter Profile Image: Marlena H.
Verified Enhanced Background Check

18. Marlena H.

Star Sitter
Shelter-animal trained pet sitter
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
8 repeat clients
from
$50
per night

I could tell our pup had such a nice time with Marlena. She was punctual, asked good questions, and was quick to respond both when booking and during the stay. And she sent some sweet photos of our camera-shy dog. Would be glad to have her sit again!

Calendar Recently Updated
Sitter Profile Image: Sujae V.
Verified Background Check
Sitter Profile Image: Sujae V.
Verified Background Check

19. Sujae V.

Love and attention for all animals
Chicago, IL, 60608
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
5 repeat clients
from
$60
per night

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

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

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