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
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Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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1. 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
Profile image

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 dog’s potty schedule and play routines. Our apartment was also so clean when we got home from our trip. We will definitely work with Emily again in the future!

Sitter Profile Image: Lindsay J.
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Sitter Profile Image: Lindsay J.
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2. 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
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Lindsey is wonderful! She took great care of a cats and our place while we were traveling. She was great at keeping us in the loop and making us aware of any issues. She'll be our go to cat sitter!

Sitter Profile Image: Megan W.
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Sitter Profile Image: Megan W.
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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
61 reviews
17 repeat clients
from
$65
per night
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Megan was great with barrel. Barrel is a little timid with new sitters but Megan gave her space to come out on her own. Once barrel opened up, she was very playful and had a great time.

Sitter Profile Image: Kaitie G.
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Sitter Profile Image: Kaitie G.
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4. 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
10 repeat clients
from
$75
per night
Profile image

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 :)

Sitter Profile Image: Pablo V.
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Sitter Profile Image: Pablo V.
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5. Pablo V.

Rover 101
Fun walks
Chicago, IL, 60642
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
243 reviews
96 repeat clients
from
$66
per night
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Pablo stayed at our home for over a week to watch our dog Bently and we were so impressed. He went above and beyond and Bently absolutely loved him. He provided us with frequent updates, took care of our plants and cleaned up a mess when Bently got sick. We would strongly recommend Pablo for anyone considering him.

Sitter Profile Image: Otis B.
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Sitter Profile Image: Otis B.
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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
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Otis did a great job with Bonita, she was happy and healthy after 15 long day away. There was lack of communication but overall I recommend him to take care of your doggy.

Sitter Profile Image: Ann Marie M.
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Sitter Profile Image: Ann Marie M.
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7. 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
30 repeat clients
from
$90
per night
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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!

Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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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
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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.

Sitter Profile Image: Munder S.
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Sitter Profile Image: Munder S.
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9. 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
130 reviews
47 repeat clients
from
$66
per night
Profile image

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!

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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10. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60616
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
42 repeat clients
from
$65
per night
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Crystal did a great job with our Monty. She was even ready to extend when our flights were cancelled and we were struggling to get back in time. Lots of check-ins and photos - all very reassuring!

Sitter Profile Image: Allison J.
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Sitter Profile Image: Allison J.
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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
Profile image

Allison is a fantastic sitter! She stayed overnight with our lab-shepherd mix, Luna, while we were out of town for a wedding. She was communicative throughout the process, sending regular text and photo updates, and she did a great job taking care of our rather grumpy old dog.

Sitter Profile Image: Taylor M.
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Sitter Profile Image: Taylor M.
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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
Profile image

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.

Sitter Profile Image: Nicole C.
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Sitter Profile Image: Nicole C.
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13. Nicole C.

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

Nicole is awesome. She stayed with our pups over 6 days in our home. She followed all our instructions and treated the pups like her own. She catered to their individual personalities and needs. Awesome communication and lots of photos. Nicole continued caring for the dogs even though she got sick that weekend. She left our place spotless. Highly recommend!

Sitter Profile Image: Reshunda B.
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Sitter Profile Image: Reshunda B.
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14. 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
3 repeat clients
from
$30
per night
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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!

Sitter Profile Image: Jasmine V.
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Sitter Profile Image: Jasmine V.
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15. Jasmine V.

Rover 101
Star Sitter
Animal lover! :)
Lower West Side, Chicago, IL, 60608
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
6 repeat clients
from
$60
per night
Profile image

Jasmine kept my dog and cat over a long weekend and stayed in my home. She was polite, kept me updated often with notes and photos, she was prompt in our meeting and left my house spotless. Most importantly - my pets were well cared for and happy when I returned. 100% would book again!

Sitter Profile Image: Johnathan W.
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Sitter Profile Image: Johnathan W.
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16. Johnathan W.

A friend that cares
Loop, Chicago, IL, 60642
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
15 repeat clients
from
$88
per night
Profile image

Jonathan took such good care of our dog while we were away! They went on long walks and our dog looked super happy in every picture he sent. Jonathan sent descriptive updates and communicated as needed. We never worried about our pup while we were away. Thanks, Jonathan!

Sitter Profile Image: Amanda J.
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Sitter Profile Image: Amanda J.
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17. 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
31 reviews
11 repeat clients
from
$50
per night
Profile image

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

Sitter Profile Image: Becca C.
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Sitter Profile Image: Becca C.
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18. Becca C.

Looking for pups to take care of!
Near West Side, Chicago, IL, 60607
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
5 repeat clients
from
$45
per night
Profile image

Snoopy loves spending time with Becca. I can see his excitement in the update pictures I receive! I appreciate the open communication, flexibility and consistency. :)

Sitter Profile Image: Callie L.
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Sitter Profile Image: Callie L.
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19. 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
6 repeat clients
from
$50
per night
Profile image

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.

Sitter Profile Image: Marlena H.
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Sitter Profile Image: Marlena H.
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20. 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
Profile image

Marlena was flexible and responsive. Our dog was relaxed when we returned home later than scheduled and it was apparent that he had fun hanging out with her. We hope to be able to schedule her for dog sitting again in the future!

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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.

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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.

Want to learn more? Check out reviews from pet owners who have used Rover.

House Sitting