House Sitting Near West Side

Find a loving house sitter to watch over your pets and your home.

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Over 498
pet parents in Near West Side have booked house sitting

Near West Side, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Faith M.
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Faith M.
from
$60
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60622

Faith was able to fulfill a last minute house sitting request for my girls and she did a great job caring for them! Very communicative, sent photos, gave snuggles and love, and was very respectful of our home. Will definitely book her again in the future!

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Rachel H.
Sitter Profile Image: Annie C.
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Annie C.
Star Sitter
from
$60
per night
5.0 out of 5 stars
52 reviews
25 repeat clients
20 years of experience
Chicago, IL, 60607

Annie truly went above and beyond this past week, & I can’t express enough good things about her as a person & caregiver!!! She took such amazing care of my pups & it was abundantly clear they were very loved & cared for every single moment I was gone. I’ve honestly never felt so at ease leaving them with someone (including my own family & friends)! She treats your dog(s) like they’re her own, with boundless love, patience, & consistency, & it made the whole experience completely stress-free for me. She is also just a genuinely kind & wonderful person — I’d be friends with her outside of Rover in a heartbeat! I would absolutely recommend her to anyone, especially if you’re someone who gets anxious about leaving your pets with other individuals for a variety of reasons. She’s the kind of person you can fully trust, is a lovely person to interact with, & means everything wholeheartedly. Thank you for everything, Annie!!!

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Maura K.
Sitter Profile Image: Chloe P.
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Chloe P.
Star Sitter
from
$50
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
4 years of experience
Near West Side, Chicago, IL, 60661

Chloe is amazing! She took the time to get to know my girls and make the experience comfortable, safe, and fun for them. I would 1000% her to any of my dog parent friends!

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Hillary D.
Sitter Profile Image: Jessica S.
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Jessica S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
39 reviews
14 repeat clients
5 years of experience
Near West Side, Chicago, IL, 60607

Jessica was great with watching our 5 month old puppy. She was communicative and did a great job adapting to his behavior. Would not hesitate to work with her again!

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Mike N.
Sitter Profile Image: Omar C.
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Omar C.
from
$60
per night
4.9 out of 5 stars
68 reviews
23 repeat clients
16 years of experience
Near West Side, Chicago, IL, 60661

I appreciate that Omar took the time to meet with me beforehand so my dog could get comfortable with him, that actually makes a big difference. He followed all the instructions I provided. My place was left exactly how I left it which shows he respects my space, and that’s always a plus. I’m booking him again soon!

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Daritza H.
Sitter Profile Image: Eliana B.
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Eliana B.
from
$40
per night
3 years of experience
Lower West Side, Chicago, IL, 60608

About: I've taken care of dogs for my neighbors and family friends throughout middle school and into high school! I have experience walking dogs and taking care of them when their people were on vacation! I am happy to send pictures or videos updates of your pup and will gladly play with them! I am excited to have wide availability to take care of animals! I am open to mornings, evenings, and would be more than happy to stay overnight! I really enjoy spending time with animals! It's important to me to get to know your pet! I would love for you to share with me how you care for your pets, so that I can care for them as well as you do! I love to cuddle, play, and engage with all dogs and cats!

Sitter Profile Image: Dana K.
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Dana K.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
7 years of experience
Near West Side, Chicago, IL, 60654

Dana did a wonderful job watching our two cats while we were out of town. He was available on short notice, which we really appreciated, and even took the time to meet with us beforehand so everyone felt comfortable. While we were away, he communicated regularly and sent pictures, which gave us great peace of mind. When we returned, everything was clean and well taken care of and our cats were clearly happy and comfortable. Dana was reliable, thoughtful, and easy to work with. I would absolutely recommend him to anyone looking for a trustworthy pet sitter! Thanks Dana

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Heidi W.
Sitter Profile Image: Ariana B.
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Ariana B.
from
$65
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
4 years of experience
West Town, Chicago, IL, 60612

Ariana was wonderful taking care of our puppy and home. Great communication and is so very sweet and caring for Animals. We can't recommend her enough

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Marc D.
Sitter Profile Image: Samantha E.
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Samantha E.
Star Sitter
from
$40
per night
5.0 out of 5 stars
141 reviews
61 repeat clients
13 years of experience
Loop, Chicago, IL, 60602

Samantha is amazing. She took care of my two Frenchies for 8 days in my home. She took over new training techniques for the puppy with no problem (with very little notice I might add). She took amazing care of my babes and left my apartment just as I’d left it. Love her!

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C A.
Sitter Profile Image: Emily N.
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Emily N.
Star Sitter
from
$68
per night
5.0 out of 5 stars
234 reviews
66 repeat clients
10 years of experience
Chicago, IL, 60605

Emily was great with my senior pup, Bailey! She kept me updated and sent great photos the entire time I was out of town. On top of the great care she took with both Bailey and my place, she was amazingly flexible and able to extend her stay when we had to stay out of town an extra day. Definitely recommend Emily and plan to book again with her!

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Annie H.
Sitter Profile Image: Mairead M.
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Mairead M.
Star Sitter
from
$65
per night
5.0 out of 5 stars
26 reviews
4 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

This was my first time booking with Mairead so I was a little nervous, but she quickly put my mind at ease. She took the time to do a meet & greet and made an effort to learn my pup’s routine beforehand. She consistently kept me updated while I was away. I never had to wonder how my pup was doing because she was very proactive with communication. She also went above and beyond with his meals, knowing he doesn’t usually like to eat when I’m away and made great effort to ensure he was comfortable and eating. I also came home to my place exactly as I left it. I highly recommend Mairead to anyone looking for a reliable and caring sitter.

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Daritza H.
Sitter Profile Image: Jorie S.
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Jorie S.
from
$70
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
15 years of experience
Chicago, IL, 60605

Jorie was absolutely amazing! This was my first time using Rover for an overnight stay, and she made the entire experience so easy and comforting. We met in person for a meet-and-greet, and she was incredibly friendly and truly engaged in getting to know my pup, which meant so much to me. I left detailed instructions, and she followed everything perfectly. She also left my home exactly how she found it, which I really appreciated. Jorie kept me consistently updated with texts, photos, and messages after every walk, which gave me so much peace of mind. Leaving my puppy is always hard, and the worry is real but Jorie completely eased my anxiety. I’m so grateful for her care and would absolutely recommend her to anyone looking for someone trustworthy, attentive, and kind. ❤️

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Azure D.
Sitter Profile Image: Christopher W.
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Christopher W.
from
$55
per night
4.9 out of 5 stars
62 reviews
30 repeat clients
8 years of experience
West Town, Chicago, IL, 60622

Sage was great! He provided updates and photos daily and I was able to enjoy my vacation without worrying about my lil fur baby. Would recommend!!!

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Mai S.
Sitter Profile Image: Stephanie O.
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Stephanie O.
Star Sitter
from
$75
per night
5.0 out of 5 stars
44 reviews
8 repeat clients
13 years of experience
Near West Side, Chicago, IL, 60608

Stephanie was awesome! She arrived on-time and was very professional. I would highly recommend Stephanie. We plan to rebook her services again.

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Nicole B.
Sitter Profile Image: Dominique P.
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Dominique P.
Star Sitter
from
$76
per night
5.0 out of 5 stars
84 reviews
44 repeat clients
7 years of experience
West Town, Chicago, IL, 60622

Dom was great with Rani and made us feel comfortable leaving her for the weekend! She sent daily updates and made sure to adhere to the guidelines we had for her. Dom was clean, prompt, and communicative - would definitely work with her again!

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Sanjana R.
Sitter Profile Image: Carolyn P.
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Carolyn P.
from
$65
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
13 years of experience
Chicago, IL, 60642

Carolyn did such an amazing job housesitting. I had to book last minute due to an emergency and she was at my place within an hour. My apartment looked just as it was when I left it, and Carolyn followed instructions perfectly. She was very communicative and very thoughtful with my anxious dog. I am so glad to have found her in such a pinch and will definitely be booking with her again!

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Olivia R.
Sitter Profile Image: Anthony A.
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Anthony A.
from
$50
per night
5.0 out of 5 stars
7 reviews
3 repeat clients
6 years of experience
West Town, Chicago, IL, 60622

Anthony has quickly become our favorite pet sitter in Chicago! Very reliable, communicative, and takes great care of our elder dog with quite a lot of needs while we are at work. Thank you!

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Richard C.
Sitter Profile Image: Tammy G.
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Tammy G.
Star Sitter
from
$40
per night
5.0 out of 5 stars
14 reviews
8 repeat clients
5 years of experience
North Center, Chicago, IL, 60613

Had a great experience with Tammy, who provided in-home dog-sitting for our two dogs while we were away for a couple of weeks. She was kind, professional, communicative, and took very good care of the fur babies. We returned to a tidy house and a couple of happy, healthy doggos. Will definitely ask her to sit for us again, and would recommend her to others!

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Meghann C.
Sitter Profile Image: Allison D.
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Allison D.
from
$75
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
11 years of experience
Near West Side, Chicago, IL, 60661

My goodness Alli is seriously THE BEST sitter I've ever had on this platform!! Her communication style is unmatched and exactly what I'm looking for when it comes to providing updates on my little one while I'm away. She provided detailed check-ins at/around the same time each day, which gives me so much peace of mind (I can still enjoy my time away while also knowing I'll receive a check-in at specific times that day). She followed all care instructions to the letter, kept my home spotless, and overall had an awesome time with Atlas. Without a doubt I will be booking her services again in the future! Thank you Alli!!

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Rachel W.
Sitter Profile Image: Laughlin C.
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Laughlin C.
from
$45
per night
4.7 out of 5 stars
4 reviews
2 repeat clients
22 years of experience
West Town, Chicago, IL, 60622

About: I'm a lifelong dog lover and would love to share some time with your furry friend! I love exploring the area with leash in tow and will make sure your dog gets ton of attention, activity, and love. About this sitter: I am a life-long dog lover who has always had a dog. I'd love to visit with your pup, take some walks, and keep them company while you are away. I have lived with large dogs and small dogs (Newfoundlands to a Papillon) and was the care-taker for my school's mascot, Jack the Bulldog. Why I love dog sitting I have always had dogs in my life, from the days of resting my two-year old head on our Samoyed at nap time to running around San Francisco, Chicago and LA with my four legged friends. I am yet to meet a pup that I can pass up without a quick pet or pat on the head. I am a fully remote employee for my "day job," so that allows me the flexibility to tailor my schedule to each dog's needs. My living space provides plenty of space for pups to stretch out and relax. I am a push over for allowing dogs up on the couch and have dog beds on the floor as well.

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The median cost per night for house sitting in Near West Side is $50

Pet parents share their Rover experiences - Near West Side

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5.0 out of 5 stars

Gabriela was such a blessing to us during an unexpectedly busy week. She stayed with our dog for one day and did a fantastic job walking her and keeping her company. We have a chihuahua mix whose personality is quite spicy — Gabriela handled her with ease. 100% would book with Gabriela again.

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Elizabeth G.
House Sitting
5.0 out of 5 stars

Linh has been taken care of my cat for a couple of months now and is super trustworthy, reliable and communicative.

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Kelsie M.
House Sitting
5.0 out of 5 stars

Victor was truly an amazing sitter and we could not recommend him more! He took such great care of both our dog and cat while we were away, including administering our cat’s meds 2x a day, and they both absolutely loved him. He communicated with us multiple times a day with updates and pictures, which made it so easy to relax and enjoy our vacation knowing they were happy and well cared for. He was also incredibly respectful of our apartment, and we came back to a spotless place and two very happy animals. Victor is kind, calm, reliable, and clearly really great with pets. Truly everything you could want in both a pet sitter and house sitter. We will 100% be booking him again :)

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Annie F.
House Sitting
5.0 out of 5 stars

Zhanna is absolutely wonderful! She has been taking exceptional care of my Maine Coon, Onyx, and I’m so impressed by how patient, gentle, and attentive she is with him. Onyx is a big boy with a LOT of fur and definitely has his own opinions about literally everything, but Zhanna somehow knows exactly how to handle him. She takes her time and always pays attention to the little things. What I appreciate most is how much she genuinely seems to care about the animals she works with. That kind of personal attention is hard to find! Having someone I completely trust with Onyx means so much to me. Zhanna is professional, reliable, kind, and truly exceptional at what she does. Five stars without hesitation! ❤️🐾

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Violeta B.
House Sitting
5.0 out of 5 stars

Tylisha was great! Very responsive, prompt, lots of photos shared and Airlie seemed very happy when I got home. House was clean and tidy. Highly recommend!

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Dane C.
House Sitting
5.0 out of 5 stars

I cannot recommend Ariana enough! She is SO sweet and my sometimes shy baby immediately was drawn to her at the meet and greet. I was so nervous leaving her for the first time since moving and was so relieved to have her in such great hands. Ariana sent lots of pictures, spent time playing and cuddling my stage 5 clinger. She went above and beyond with cleaning the litter box and taking out the trash without me even asking which was such a nice thing to come home to. We love Ariana!!

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Kenzie H.
House Sitting
5.0 out of 5 stars

Elissa is an absolute dream! I am a very nervous pet owner, and she was so communicative and helpful. Our dog immediately fell in love with her, and we were able to enjoy our weekend because of Elissa's diligence. We cannot wait to use her again!

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Niko Z.
House Sitting
5.0 out of 5 stars

Meg did a great job taking care of Finn and Maisie! Communicated updates on how their days were going and left my place super clean! Would not hesitate to book Meg again!

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Michaela S.
House Sitting
5.0 out of 5 stars

Chelsea did a phenomenal job watching Finn and Maisie! She was great with proactive updates and photos. I would not hesitate to book her again! She also left my home super clean.

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Michaela S.
House Sitting
5.0 out of 5 stars

As usual, Jena was amazing. She has stayed at our place twice now with Gus and he’s always very happy and relaxed when we return home, as if we hadn’t left at all. Our place looks great and we trust Jena to be in our home and take care of Gus. We hope to have her back again in the future!

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Ashley B.
House Sitting
5.0 out of 5 stars

Kai’s communication was great, our house was just as clean as we left it, and most importantly, our baby TT was well cared for. Highly recommend Kai!

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Mary H.
House Sitting
5.0 out of 5 stars

Stefanie could not have been better with my dog, Dino. She was attentive and loving. I got many updates and photos, which made me feel at ease. She left my house so clean and tidy. I’d love for her to watch Dino anytime I need help!

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Julie W.
House Sitting
5.0 out of 5 stars

Kaia did a great job with my particular pup Bear! She was attentive and patient, respecting his boundaries and paying attention to his needs. She house sat for me while I was out of town, responsive with communication and kept my house clean!

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Sindhu S.
House Sitting
5.0 out of 5 stars

Samantha is the best! It’s always sad to leave our pup but knowing he’s in such great hands is very comforting.

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Mary A.
House Sitting
5.0 out of 5 stars

If I could give Caline a million stars I would. She is so friendly, communicative and caring. My dogs absolutely adored her and seemed so happy and content in all the pictures. I wouldn’t hesitate to recommend her to anyone. She’s great and I’m excited for her to look after the pups again.

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Anna B.
House Sitting
5.0 out of 5 stars

Polina is amazing. She stayed at our house for 8 days and our shy cat was so comfortable with her. Not only is she a great cat sitter, but also a great house guest. We will have Polina back anytime we can.

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Julianne B.
House Sitting
5.0 out of 5 stars

Milena did a great job watching Charlie. She's stayed over for us twice now, and Charlie loves her. She has also been responsive, concise, professional and timely - which is very appreciated.

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John M.
House Sitting
5.0 out of 5 stars

Dom took such amazing care of Goose, a two year old energetic golden retriever, while I was away for the weekend!

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Olivia G.
House Sitting
5.0 out of 5 stars

Anastasiia is so thoughtful and takes such good care of my dog Biscuit! Biscuit was injured and she handled her meds and routine with the utmost care, and even brought her a little toy to make her feel better. I am so grateful to have Anastasiia take care of my pup!

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Lauren W.
House Sitting
5.0 out of 5 stars

Cabella loved snuggling with Teresa. She's very knowledgeable and I was comfortable leaving my spicy dog with her. Thank you!

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Andrei I.
House Sitting
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