Personalized care for your dog or cat - Woodlawn
Highly-rated overnight sitters - Woodlawn
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Simply put, Dwight is everything you’d want in a dog sitter. He works from home, has a yard, and makes sure the dogs have a lot of activity. He is incredibly responsive and sends great photos to keep you updated. Beyond that, he’s just an awesome guy. I have a demanding schedule and he is incredibly flexible and willing to accommodate. Will use over and over again.”
“Kamiah and Casius were great sitters for Bailey. For me, it was a very last minute booking and Kamiah was incredibly accommodating to make it work. She was also very quick to contact us on the first day when Bailey wasn't eating (but everything was fine, as this is how Bailey always is at a new place), and Bailey looked very happy in the photos and videos we got each day. Also, Kamiah's pick-up and drop-off were prompt and efficient. I definitely plan to use them again!”
“My dog was so calm after I picked him up boarding with Kyla. Energetically, I could tell that he was very well taken care of with her - no stress, no anxiety, just peace. TY KYLA!!!”
“Chelsea is such a wonderful sitter !!! My dog absolutely loves her and her family. It’s great knowing that my dog is in great hands when I’m away and Chelsea always takes great care of her. Highly recommend Chelsea !!”
“Bernie’s hosts were wonderful, especially in the unflustered and caring way they dealt with a transportation crisis my wife and I had. They made me feel like they would have happily made extra room in their family for another week as cooly as they did for an extra day. Bernie is an untroubled, self-confident old girl who enjoys human and canine company, and this was a great environment for her with very nice dog-loving people.”
“This is the second time I've worked with Tamara. Both times she provided daily pictures with information on how Frank was doing. He came home well rested and happy. Thanks again Tamara!!🐶”
“I was so nervous about using a dog sitter for my 2 fur babies. I was especially concerned about my youngest dog who we adopted from an animal shelter because she is fearful of people she doesn’t know. MariaJose quickly put my mind and heart at ease. She boarded Prince and Bella for a week. Not only did she send messages to let me know they were doing well, she also sent pictures and videos. My babies were happy and well taken care of. I definitely recommend her as a sitter.”
“Fred was amazing to work with! He kept me updated every day and made sure to keep me in the loop with how my dog was doing. My dog can be a bit stubborn, but Fred handled it like a pro and made sure everything went smoothly. I really appreciated his communication and care.”
“Ebonee was very attentive and knowledgeable about dog behaviors. She kept us informed daily. She sent lots of pictures. I’m very happy with the service she provided and would book her again.”
“Cassandra took great care of my dog Ace during his 4-day stay. I can tell he had a good time hanging out with her dog, Chewy. Cassandra was a pleasure to work with and I hope to use her services again for future boarding.”
“Our Bernie loved staying with Joe. He understands dogs through and through, and maybe even more important, he understands and appreciates the quirks and idiosyncrasies of particular dogs. He kept us well informed and accommodated our schedule. Bernie would go back in a heartbeat, I’m sure, and we would be happy knowing she was in good hands.”
“Danielle took wonderful care of my senior pup while we were away! She was patient and attentive to his needs. Pictures were appreciated as well. I highly recommend Danielle for your pet sitting needs.”
“Katrina is an amazing caregiver. Incredibly thoughtful and caring. Excellent communication. Fun pictures. I felt completely comfortable with Katrina watching my little one 🐶🙏”
“I came back to a happy pup. Steven sent pics and gave me assurance that kelce was happy and comfortable when I was away. I hope Steven has availability next time I go out of town.”
“Ann is awesome! She kept me updated throughout Briggs entire stay and even made him food when he didn’t want to eat his own. I appreciate all the pics and attention she gave him.”
“OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.”
“Craila is our go to dog watcher. We have a high energy dog and he is definitely tired out and content after his vacations with Craila. She does a great job watching him and keeps us updated on how he’s doing which puts us at ease!”
“Ashley, on short notice and later with a cold, accepted my new puppy in her home with great energy. As of this writing, she has spent more time with my Snoopy than me, and I’m jealous. She is professional and skilled at managing multiple animals. She was a caring life saver for my impromptu two week trip out of town. Thank you again. 💜”
“Katie was great! Chloe seemed like she had a fun time with her. Katie sent lots of pictures! We also were really grateful for how accommodating Katie was - our flight was delayed and she was so nice about us having to switch around pickup plans.”
Over 4.1 million dogs curled up for a sleepover in a sitter's home on Rover1
Cat caregivers near you - Woodlawn
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Qutress is an amazing sitter. My cat felt comfortable with her very quickly and loved when she would visit. Qutress sent me thorough updates and lovely photos every time she went to check in on her. If I leave town again I’d definitely want to rebook with Qutress (and so would my cat!).”
“Coretta & her daughter were wonderful with our kitties, Charlie & ChaCha! She arrived on time, was sweet to give the boys space to feel comfortable, and spent quality time giving pets as they relaxed. Looking forward to booking her again”
“Haley was very friendly, and kept us well updated each day on how out cat was doing. Gus warmed up to her instantly. We would highly recommend her to anyone who is looking for a pet sitter, and look forward to using her again in the future.”
“Evan did a wonderful job watching our cat for a long weekend. He was communicative and responsive, which made us feel comfortable and confident that our cat was in great hands.”
“Very attentive care for my timid cat. Followed all the care instructions very exactly and made sure to seek out my cat in hiding to confirm all was well. Recommended!”
“Jasmine took great care of our kitties (2yo and 15yo). She provided daily updates and great pictures. Our older cat has a variety of health issues and Jasmine was able to give her medications and gave updates about her eating. Jasmine is fantastic!”
“I had arranged a last minute trip and my regular Rover sitter was unavailable. I got in touch with Maribel and we were able to arrange everything in a day. I got tons of photos while I was away and came home to happy cats. I’d definitely use Maribel again!”
“Dominique was AB-SO-LUTE-LY Fabulous!!! She treated my babies like her very own (even calling them by their "cutesy" baby names when she scratched them under their cheeks and behind the ears). She created a safe, loving and clean space for them... allowing them to thrive. Truth be told, I'm kind of jealous that they "took to her" so quickly and didn't miss me more (our first time separated in 11 years). Knowing Dominique was taking such great care of them, made the stressful time I was going through easier to manage. My babies came back, calm,well feldand clean!!! 👍 I will definitely seek out Ms. Dominique again for any and all future pet needs.”
“Tara visited and gave my cat so much attention while I went to an all-day conference for 4 days. She played with him, and petted and brushed him. Her photos showed a happy and engaged cat. I appreciate Tara’s great flexibility and understanding of my house, schedule, and cat! Thanks for being kind and encouraging, Tara!”
“Me’lia was a godsend, when my original sitter had to cancel last minute. She was communicative and thoughtful, and was super accommodating. And both my cat and my dog loved her. Would recommend and would rebook her again!”
“Grace is the best cat sitter we’ve ever had! She sends timely updates and photos, is super responsive, and our cats seem to be really comfortable around her. She is also really respectful of our apartment and always take the time to take out the trash and recycling and clean up before she heads out. I would trust my cats with anyone else!”
“An amazing cat sitter! It’s clear how much she truly loves animals, and they love her back. Even our very shy and unsociable kitty fell in love with her at first sight, which was a huge surprise to us. We’re so grateful for her care, kindness, and attention.”
“Kelera is so awesome!!! So friendly, professional, and helpful. Not only did she take care of the basics for our kitties while we were gone but she went above and beyond to help them get comfortable around her and communicate how they were doing. Excellent service, communication, and care! Thank you again Kelera, we will be in touch again soon 🙂”
About: My cat Clove (he goes by Miantiao, which means noodle, at home much more) knows how to high five and answers to his name. Cats are smart enough to be trained if you know how to do it and treat them right! I’m here to give them the best care they deserve when you are away :)
“I needed to book a sitter last minute and was so grateful that Kristina was available. This was my first time using Rover, and I lucked out with Kristina! My cats instantly felt comfortable with her and she went above and beyond. If you’re looking for someone reliable, kind, communicative, and responsible, Kristina is the perfect pet whisperer to look after your fur babies!!”
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Perfect for high energy dogs - Woodlawn
Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Fantastic experience with Steven! Very prompt in communication and I could tell he genuinely loves dogs. Mochi was happy during his time with them. Highly recommend”
“This was our first time using Rover, so we were a bit nervous about leaving our two pups for the day (especially a teething puppy). Dwight however made us feel at ease and we appreciated that he sent us several pictures throughout the few hours our pups were with him. He even gave our pups a new toy! Thanks Dwight !”
“Bola came through for me last minute and took great care of Bea!! She sent me picture updates and communicated well throughout the day. Will definitely be booking again with her.”
“Dayana is always so quick to respond to bookings, despite last minute requests. She is always keeping me updated throughout using video. Kitty loves going over because there is usually others dog she can play with. So happy we found Dayana!”
About: I’ve grown up with dogs in my home my entire life, so caring for dogs has always been a big part of who I am and I truly love spending time with them! I have experience walking, feeding, playing with, and caring for dogs of different ages, sizes, and personalities. I know how important it is to have someone you trust caring for your dog, so I treat every pup like they’re my own. Whether your dog is staying with me for the day or just needs a walk, I’ll make sure they get plenty of attention, exercise, playtime, and, of course, lots of love and cuddles! I’m dependable, patient, and attentive, and I’m always happy to follow your dog’s normal routine and any specific instructions you provide. My goal is for both you and your pup to feel comfortable, safe, and happy while they’re in my care! 🐾 I currently have a very flexible schedule and am available for pet care throughout the week! I’m happy to provide daytime care, walks, drop-ins, and plenty of attention throughout the day. As a teacher, my schedule may change once the school year begins, but I plan to continue offering pet care before and after school, in the evenings, and on weekends. I’m flexible and happy to work with you to find a routine that works best for your pet! Your pet’s safety and comfort are always my top priorities. I’ll follow your pet’s normal routine, feeding schedule, walking preferences, and any specific instructions you provide. When caring for dogs in my home, I’ll make sure they have a comfortable, safe environment with plenty of attention, playtime, walks, and opportunities to relax. I’m also happy to accommodate crates, special routines, or other needs to help your dog feel as comfortable and at home as possible.
“Anna was an amazing dog sitter! She sent us great pictures and updates throughout the day, was very communicative, and Moose seemed to have an amazing time with her! 10/10 would use her again!”
“When I first saw Jennifer I knew right away that I could safely leave my dog to her. Cola had a great time with Jen and her family while we had a whole day trip in Chicago city. It’s very convenient that her place is only 15 mins away from the downtown area. Thank you Jen and family -Ryan from Minnesota”
“I have an unexpected conference to attend in Chicago. I needed someone to watch my baby for me. Pamela was quick in her response, flexible and very caring. She literally save me. Thanks again”
About: I’ve taken care of dogs ever since I was a young kid. When I was in college, I cared and trained a puppy to its adult years all by myself! He is now 6. I am a professional in Tech that is fully WFH! I am looking to work around my flexible schedule to spend time with your pet. I will always treat your home with respect and leave it the way it was before I got there. I have walked many kinds of dogs as well.
“Demetra was great! She took care of buzz so well that we’d like to book her again in the near future. She was super responsive, flexible and took our little furry boy for nice/long walks. I definitely recommend Demetra!!”
About: I grew up taking care and even sitting some of my mom's friends dogs. In my teens I would take care and sit a few family members dogs. I then volunteered at a puppy adoption center in Mexico. I am currently only attending school on Friday mornings from 8am to 12pm. I will update my schedule once I go back to tutoring or when my classes change. I will ensure that your pets get the care they need and the exercise they need. I will also pay attention to any requests your pets may need.
“Jaclyn was super prompt in her responses, kind, and super sweet for my dog! Communication was excellent, and she made sure that Billie not only was taken care of but that she met her social and physical exercise for the day with enrichment time at the farmers market! I would definitely rebook her again and recommend Jaclyn to anyone!”
“We were in a pinch while visiting Chicago! Our dogs decided to howl while we were out the very first light and the condo sent two warnings….third time- we were out! I contacted Michael in desperation to see if he could help take care of the dogs while we explored the city. He was very quick to respond! And he said yes! Why did i chose him out of all the pet sitters in Chicago? He had a friendly face and i just felt that he would be a total buddy to the dogs. And he was great! He is located in a central location, communicated throughout the day (and sent pics of my dogs totally taking advantage of the opportunity to be comfortable) explored the city with them and seemed to enjoy having them for the two days! He even got a kiss on day two from Rooney! It is so hard to leave your dogs with someone you don’t know- but Michael did a phenomenal job with my pups. I highly recommend him to anyone visiting Chicago as a trustworthy person to care for your furry friends.”
More than 1.6 million pets enjoyed cuddles and care from sitters on Rover1
Adventure-ready dog walkers - Woodlawn
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Artiss has walked my pup multiple times, and he has always been happy to see her! She has done a great job managing his high energy level, sent wonderful photo updates, and always made sure he went to the bathroom.”
“Roxy is the best. If I could, I would give her 10 stars. Amber has had 3 walks with Roxy now and she loves it. Amber is a 8 month old puppy who is not easy to handle. Roxy takes her time to make my pup comfortable and happy. She gives out a gist at the end of each walk and it really gives me a collective idea on how to train my dog. We are really happy with Roxy and we are planning to be her repeat client.”
About: I have experience caring for both energetic dogs who need structure and movement, as well as more sensitive pets who benefit from patience, gentle routines, and clear communication. I’m organized, responsive, and great at managing schedules—skills I use every day in my professional work and bring directly into pet care. I pay attention to details, follow instructions carefully, and make sure owners feel fully informed while they’re away. I’m a reliable and attentive weekend pet sitter based in Boston, and I take pride in creating a calm, safe, and caring environment for every animal I look after. I work a full-time remote job during the week, but on weekends I’m fully dedicated to pet care—whether that means long walks, dedicated playtime, or simply keeping your pet company and relaxed at home. As someone who values consistency and trust, I make sure every pet gets thoughtful, individualized attention. Whether your pet needs slow, steady walks, a playful activities, or lots of affection, I’m here to help your weekend feel stress-free. If you’re looking for a sitter who is responsible, communicative, and truly loves spending her weekends with animals, I’d love to support you and your pet!
“Tamara has been walking my dog Blowe daily since this summer, and I honestly couldn’t ask for better care. Blowe genuinely looks forward to his morning walks with her and always comes back happy and relaxed. Having someone I trust with him every day gives me real peace of mind.”
“Ryann was great with our puppy who has tons of energy and can be a handful at times! She sent plenty of updates and was very respectful and responsive in communications. Definitely will book again!”
“Lillian has been great with my dogs and very communicative throughout the walks. She took the time to make sure they were comfortable, shared updates and photos, and went above and beyond with their care. I really appreciated her flexibility and willingness to work with my schedule, especially while I was out of town. I felt confident knowing my dogs were in good hands, and I would absolutely recommend her to other pet parents.”
“Me’Lia was absolutely wonderful! She took great care of our Sandy! Me’lia was punctual very patient with handling Sandy. Will definitely rebook in the future!”
“We have been consistently using Beverly since our pup was 3 months old. Beverly does weekly walks for us as well as daycare and overnight stays. Charley loves her Beverly and she has quickly become part of our family.”
“Kim did a fantastic job handling and walking my very active yellow Labrador. She was very friendly, communicative, prompt and she followed some of the direction we had left her. Really appreciated her last minute help in caring for our dog! Highly recommend”
“Teddy finished his first week with Sonya & Bobby. He let his hair down as usual and was his goofy, snotty self. Hats off to you guys for giving Teddy a chance. He needs the walks & attention. You are so professional & pleasant. You must love dogs because Teddy is hard to reach. But he's happy.”
About: I have taken care of friends and clients dogs. The longest I watched a dog was 2 weeks. She is an Australian Shepherd and Boxer mix (high energy and very smart). Others breads I have taken care of are Doberman, Labradoodle, French Bulldog, Pit Bull, and Bulldog. Long walks and playtime are no biggie! Just a note, my household is just me and my boyfriend. I wake up at 6:30-7am, go on a walk, breakfast, play time, snack, nap (if needed, walk or play, relax, and dinner. I adjust to the needs of the dog, especially with physical activity. I am comfortable with high energy and low energy dogs. They will get a lot of love and encouragement the whole time. I live in a condo in a 12 story building. It is a dog friendly building with fenced in a play area. It is small but an easier way for any dog that needs to be let out. There are a couple of dog parks to walk to but can avoid and just walk if that is more comfortable for them.
About: I’ve taken care of cats and dogs for the past 7 years. I’m currently the go to cat and dog sitter in my apartment building! I am trusted to handle a pet’s feedings, walks, and playtime. I work full time, Monday through Friday, 9-5. After work and on the weekends I love to take a break to hang out with furry friends! It’s important to me that your pets are well loved and cared for! I follow pet owner’s care instructions carefully to ensure pets and their parents are happy!
“Manuela did a great job! My dog Ella really enjoyed walking with her. Manuela is punctual, reliable. My dog doesn't trust people easily but with Manuela, it was easy. Amazing! Thank you so much. ?”
“Victoria was able to be there for my puppy when I needed her in a pinch! I’m so grateful for her! She was great with him during a busy season of my life! Thank you Victoria!!”
About: Hi! My name is Arie and I can not wait to meet your furry family members! I have spent my whole life caring/loving dogs, so I understand what it means to say that doggies are a part of the family. This is why I promise to treat your baby with the exact same love and patience that I treat my own. I offer a variety of personalized services to keep your pet happy, healthy, and safe, such as dog walking, house sitting, and frequent photo updates so you never miss your furry friend too much! I'm currently in school and working online, with this, your pet will rarely be left alone and will receive lots of attention throughout the day. I can take dogs out every 1 to 2 hours for quick backyard play or bathroom breaks. Additionally, I am available for early morning walks, midday check-ins, overnight stays, and weekend care. flexible with caring for your doggie. I have a fenced in yard and my own doggie named Pinky. She is very playful and loves to meet new dogs. If you prefer for me to come to your home, I would be happy to do so.
Over 980,000 dogs traded couch time for play time with Doggy Day Care on Rover1
Large dog specialists near you - Woodlawn
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Chelsea is such a wonderful sitter !!! My dog absolutely loves her and her family. It’s great knowing that my dog is in great hands when I’m away and Chelsea always takes great care of her. Highly recommend Chelsea !!”
“Bernie’s hosts were wonderful, especially in the unflustered and caring way they dealt with a transportation crisis my wife and I had. They made me feel like they would have happily made extra room in their family for another week as cooly as they did for an extra day. Bernie is an untroubled, self-confident old girl who enjoys human and canine company, and this was a great environment for her with very nice dog-loving people.”
“This is the second time I've worked with Tamara. Both times she provided daily pictures with information on how Frank was doing. He came home well rested and happy. Thanks again Tamara!!🐶”
“I was so nervous about using a dog sitter for my 2 fur babies. I was especially concerned about my youngest dog who we adopted from an animal shelter because she is fearful of people she doesn’t know. MariaJose quickly put my mind and heart at ease. She boarded Prince and Bella for a week. Not only did she send messages to let me know they were doing well, she also sent pictures and videos. My babies were happy and well taken care of. I definitely recommend her as a sitter.”
“Fred was amazing to work with! He kept me updated every day and made sure to keep me in the loop with how my dog was doing. My dog can be a bit stubborn, but Fred handled it like a pro and made sure everything went smoothly. I really appreciated his communication and care.”
“Our Bernie loved staying with Joe. He understands dogs through and through, and maybe even more important, he understands and appreciates the quirks and idiosyncrasies of particular dogs. He kept us well informed and accommodated our schedule. Bernie would go back in a heartbeat, I’m sure, and we would be happy knowing she was in good hands.”
“Danielle took wonderful care of my senior pup while we were away! She was patient and attentive to his needs. Pictures were appreciated as well. I highly recommend Danielle for your pet sitting needs.”
“Gus has stayed with Iwona countless times, each one better than the last! He is so loved and cared for in Iwona’s home, he pulls me to her front door! Cannot recommend her enough”
“I came back to a happy pup. Steven sent pics and gave me assurance that kelce was happy and comfortable when I was away. I hope Steven has availability next time I go out of town.”
“Craila is our go to dog watcher. We have a high energy dog and he is definitely tired out and content after his vacations with Craila. She does a great job watching him and keeps us updated on how he’s doing which puts us at ease!”
“Katherine and her partner did a wonderful job taking care of my Aegon and I'd be delighted to have him stay there again! Cuddles and trips to the dog park, frequent communication and even a stuffy that my pup loved while he was there to take home! A great relief to have my boy cared for while I was away.”
“Ashley, on short notice and later with a cold, accepted my new puppy in her home with great energy. As of this writing, she has spent more time with my Snoopy than me, and I’m jealous. She is professional and skilled at managing multiple animals. She was a caring life saver for my impromptu two week trip out of town. Thank you again. 💜”
“Christine did an absolutely amazing job watching our 5-month old puppy! She sent photos and updates throughout the day, had lots of supplies so we didn’t have to pack too much, and even sent him home with an adorable Polaroid and treat bag. 100% your pup is in the right hands with Christine!”
“Katie was great! Chloe seemed like she had a fun time with her. Katie sent lots of pictures! We also were really grateful for how accommodating Katie was - our flight was delayed and she was so nice about us having to switch around pickup plans.”
“Ashley was great and took great care of our dog. She was communicative and sent a bunch of photos to make sure we were updated on how he was doing. Took him to the dog park, on walks, etc. Made us feel completely at ease while we were on a trip.”
“Shayna was excellent! We were very nervous leaving our overly anxious labradoodle for a few days and Shayna put all of those nerves to rest. She is clearly a professional. Thank you so much for everything Shayna!”
“Keri and her family were amazing! We were driving in from out of town and she worked with us on drop off and pickup times and gave our Rooty soooo much love. If I could give 6 stars, I would!”
“I had a great experience with Scott as always. He took wonderful care of Bambi and kept me updated throughout the stay. It was clear Bambi was comfortable, happy, and well cared for.”
“Randall was having stomach issues before being dropped off to Angel. He kept me updated and gave great care. Happiest dog ever after Angel watches him.”
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1Global data from Rover (November 2025)