Windy City Dog Walkers is an awesome company. They are a professional service, extremely reliable, flexible, and accommodating to schedule changes. I have been using Windy City for over 5 years now and never been disappointed. Dog walks occur on time with individuals who care and treat your pet as their own. Our current dog walker, Victoria, is an amazing person. Every day our dog is so excited to see her and she manages to get hime outside in all types of weather and condition to make sure he gets the exercise he needs. We truly appreciate Victoria's lovely care of our pet. Windy City Dog Walkers are truly 5 out of 5. Highest recommendation. read more

The whole team at Windy City Dog Walkers is amazing. You get a dedicated dog walker, and they do a free meet and greet at your place to make sure it is a fit. Jordan is absolutely amazing. Mermaid (my do) gets excited to see them, but Jordan is not hesitant to message in the moment with any issues and/or concerns, such as when Mermaid laid down and refused to leave for a walk. The admin team is also extremely responsive and not just before and right after you commit. The app through which you do communication, scheduling, and payment is intuitive and easy to use. They also provide daily walk report with pictures in the app. Overall, I can't recommend Windy City Dog Walkers more. read more

Windy City Dog Walkers - Dog Walkers Near Me - Chicago, Illinois

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I adopted my puppy, Arthur in June 2025. I saw his picture on the shelter's website and it was love at first sight. However, I did not have all of my ducks in a row. I work at the office four days a week, so it was imperative that I found a dependable dog walker. Frantically making inquiries, I called Windy City dog walkers. Tony answered the phone and let me know one of one of the walkers had new availability. He connected me with Cheryl who generously arranged to meet the next day. Arthur and Cheryl immediately hit it off! They have been taking walks together for a couple months now. And it's a comfort that Arthur walks every day and has formed a bond with her. I love that I receive stories about each walk and photos through their app, Time to Pet. Cheryl is a very talented photographer and storyteller! The app is very user-friendly, and I can easily communicate with the main office and with Cheryl. Windy City Dog Walkers goes above and beyond with additional services when I was going out of town last moment, I arranged a dog set through them. Cheryl stayed at my home and watched Arthur throughout the weekend. I cannot emphasize how much peace of mind they have given me! read more

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For the last three years, I have entrusted my dog to WCDW for dog walks and overnight stays. I can't imagine using anyone else! The dog walkers assigned to my dog have been caring and gentle with him. The highlight of my day is getting an email report on my dog's walk and a picture of him. Communication from WCDW and our dog walker is informative and quick. I have only good things to say about WCDW and its staff! I highly recommend them to anyone looking for reliable, high-quality dog care. read more

We moved to Chicago and needed some help with walks for our boy Mo. My friend Erin referred me and we haven't looked back. My mom (she's 77) stays with him when we travel but we still need to schedule 45min walks for him, twice a day. Ryan is our assigned dog walker and he has been so awesome. He is considerate, he cares and is patient. We have had ZERO issues and only trust Ryan. Walks are so easy to schedule via the Time to Pet app and you get pictures along with a quick report on how your pet did or anything exciting that happened during their outing. Mo is an energetic and excitable boy with a sprinkle of leash reactivity (that has improved immensely) and Ryan knows how to handle him and Mo is super happy to see him when they're out and about. My mom has also said how nice Ryan is and how he cares about Mo. read more

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We have used Windy City Dog Walkers since moving to West Town in 2023, and have been super happy with every aspect of their service. We have two reactive dogs and WCDW has been very accommodating and non-judgmental in ensuring their needs get met. We've had 3 different walkers since we started using them and each one has been 100% trustworthy and reliable. Their office staff are also incredibly responsive - my husband and I have busy, sometimes erratic schedules and they've consistently come through for us. read more

Susan, who walks my dog, is beyond wonderful and has become a member of our family. Every interaction I have had with the staff/office has been professional, responsive and understanding, and I highly recommend Windy City Dog Walkers! read more

Dog walker services through Windy City has been so helpful, especially with an ever changing schedule. I appreciate the easy scheduling and communication, and our dog loves the 1on1 on attention on his walks! read more

I've been using WCDW for 3 years now and every experience has been great! My dogs favorite part of the day is when the team comes to visit him! And my favorite is the pictures they send after each walk! I highly reccomend WCDW to anyone needing dog walking services!! read more

We have been using WCDW for 6+ years and cannot say enough good things about them! The entire team is communicative, dependable and incredibly flexible with last minute changes. Our regular walker Eris takes the best care of our pup! We would highly recommend WCDW to anyone looking for a trustworthy and consistent dog-walking service! read more

Windy City Dog Walkers has been walking my pup Daisy for years, and their service is great! Her current walker, Kat, is fantastic, and it's worth every penny knowing that my sensitive and leash reactive dog is comfortable and well cared for while I'm at work. The company itself is friendly and reliable, and it is reassuring to know that, if my walker is out for the day or I need a last minute walk scheduled, someone else will be able to step in and take care of her. I will say, too, that I had to switch to a different service after moving to the North Side because I was temporarily out of Windy City Dog Walkers' service area, and I had a very lackluster experience with the other company. I am very glad that they now have a walker assigned to my neighborhood! read more

We have had an incredible experience with Windy City dog walkers. We moved here from out of state and for the first time my husband and I both had to work on site and leave our pup at home all day. He has anxiety and can be a little reactive with other dogs so day care was not an option. We found Windy City dog walkers and they have been incredible from day 1. The team as a whole has always been responsive, up front with policies, and has very fair pricing. We love that they prioritize having the same walker each day, and Richard has been absolutely amazing. He is great with communication and sending updates with each walk. We can tell he loves our dog Winston. We can't recommend them enough! read more

I've been using WCDW for 7+ years for regular walks and vacation care for my girl JJ. Her regular walker, Rob, is so patient with her and all her quirks - and I trust him 100%! I appreciate the communication from the office - always transparent and timely with information about walk schedule changes, weather related issues, etc. I'm a big fan of WCDW and Rob! read more

Windy City Dog Walkers - Dog Walkers Near Me - Chicago, Illinois

I had a three month need for dog walking services for Birdie (my 5 year old dog). I wanted Birdie to be walked twice a day, mid-morning and mid-afternoon. Windy City Dog Walkers and Sam Taylor were spectacular. Sam always arrived on time. Sam always cleaned Birdie's paws and dried her off in the event of snow or rain. But most important of all, Birdie loved Sam, her tail would wag like crazy when he came to the door. Windy City and Sam have my highest recommendation. read more

Treats customers poorly/ poor customer service. Dog walker mentioned taking my dog to the park and dogs surrounding her. To avoid any issue, I text just to be safe and nicely ask to please make sure ruby stays on a leash. Gave him $70 dollar birthday tip week before. The dog walker cancels services going forward. I ask for my keys back he doesnt respond. I call the company and end up getting keys back hours later. Then owner calls today, is accusatory towards me and honestly pretty rude. I spent a lot of money for two walks a day to be treated poorly and with little respect for the customer itself. read more

I moved to the city recently and due to my work schedule needed help with my fur baby. It's always nerve racking because I love my dog so much and hard to trust just ANYONE with her. Windy City dog walkers were very thorough when asking about how to care for my dog which put me at ease. They also set up a meeting before you hire them to meet with your dog walker and introduce them to your dog. It made me feel so much more comfortable. Upon hiring them I have had no issues. They email you right after the walk with a detail of the visit and a picture which I loved. They are also flexible with you on if you need to add on a walk or cancel one. read more

We started working with Windy City Dog Walkers a couple months ago and we couldn't be happier with our experience! Our pups Mila and Jet love their afternoon walks with Ryan, and we get peace of mind knowing they're taken care of so well under his watch. read more

Incredibly happy with Windy City Dog Walkers. I have two ten year old dogs and we've worked with at least 5 walking companies over the years. WCDW is definitely the best. The app makes everything super easy to schedule/pay and the office is extremely responsive - even during the Christmas holidays they found a vacation sitter for me for an upcoming trip almost immediately. I've had the pleasure of meeting four of their walkers in person and they've all been incredibly attentive, adaptable, and diligent with providing updates, especially during overnight stays. read more

I could not recommend Windy City Dog Walkers enough. We have used both their dog walking and overnight stay services and always have had positive experiences. Their dog walkers and office managers are friendly, responsive, and trustworthy. The app also makes scheduling, payments, and communication super easy. read more

Windy City Dog Walkers provides great service. The dog walkers like dogs (and cats, my dog had feline siblings) and are very reliable. My favorite part of the workday was receiving a photo of Izzy on her walk. My regular dog walker Tamara was very kind and the occasional substitute walkers were very nice too. Tony, the owner, and the managers were great about communication and flexible when I need to deviate from the regular schedule. read more

Windy City walkers is the best dog walking company in Chicago! My dog absolutely adores his walker, Ali. Management is kind and organized. The daily report cards make my day! read more

We have been with a few walking services over the years and Windy City Walkers is by far the best. Pricing is reasonable/expected, but here is what stands out for me: 1 - Everything is managed through an app - its very convenient and easy to schedule, pay invoices etc. 2 - Communication/response times are frequent and fast which is super appreciated 3 - Flexibility to move my schedule around - in the post covid world I'm not in the office as regularly and my schedule can change. Its nice to not be penalized for that. 4 - We love our walker Darcy! Shes the best and sends tons of updates and pictures. Highly recommend Windy City! read more

Windy City paired us with one of our dogs favorite people. The app is so smart and easy to use, everyone is incredibly communicative and our boys are always so excited to see our same walker. The intake interview was so comforting as someone with a leash reactive dog, I never felt unsure handing him over to anyone from Windy City. Highly recommend! read more

We've been using Windy City Dog Walkers for about 2 months, ever since we had to go back to work on site. We tried Rover a few times, but weren't able to find a trustworthy walker who could guarantee a regular daily schedule. Windy City was an amazing find and we are so thankful to have them. We started with a 30 min phone call with Tony, the owner, and later had a 30 min meet-and-greet with Ric, a dog walker. The intake was suuuuper thorough. You can tell they take their job seriously and care about the quality of their service. Because of COVID, we did our meet-and-greet with Ric outside, but I would recommend doing it inside. I think it would make your pup more trusting of the walker. But who knows if that would've really help our nervous cavapoo, Charlie, who is only 1.5 years old and hasn't interacted with many people due to the pandemic Ric is amazing! When we first started, Ric asked about the commands and routines we use with Charlie. We've done many training classes with Charlie and we really appreciate that Ric tries to be consistent so Charlie doesn't learn bad habits. It took some time for Charlie to understand Ric's role, but Ric was patient and stuck with it. When Charlie would run away and Ric couldn't get him out the door, Ric would play with Charlie and let him out to pee in our backyard. Now, they're able to go on regular walks and Ric is able to get Charlie to walk back into his crate afterwards. We also like that Ric comes regularly, rather than having a different walker every time, but also like that if Ric can't come, Windy City will arrange for another walker to come. You make appointments using an app (or on the apps website). I still get to work from home every few weeks and it's really easy to cancel and book walks as needed. The app is user-friendly and you usually get confirmation responses within 24 hours. You also use the app to pay the weekly invoices. Overall, we really like the professionalism, communication, and reliability from Windy City Dog Walkers and would definitely recommend them to others! read more

It's never easy finding a new dog walking service, but I could not be happier with Windy City Dog Walkers. They are very friendly, have a very easy portal for scheduling etc., and most importantly, Casey, Tucker's walker is AMAZING. Tucker is a senior citizen with some special needs and Casey is so caring and gentle with him. And I love the notes and pictures that Casey sends. I cannot speak highly enough about Windy City Dog Walkers and Casey!! read more

10/10 for sure! I love that I can book the day prior or early morning the day of to ensure that my pup is taken care of when a long day presents itself. The dog walker provides cute pictures and a thorough review of how the walk went. Finally, the prices are really reasonable for Chicago which is refreshing! read more

I have been using WCDW for about 6 months now. Their communication is great and the dog walker is extremely friendly. They have also been extremely accommodating when I need to cancel or need to add a last minute walk. I can't recommend Windy City Dog Walkers enough, our pup loves them! read more

Windy City Dog Walkers - Photo of Nola from Dog Walker - Dog Walkers Near Me - Chicago, Illinois

Windy City walkers is the best! I love my dog walker, Gabby!! They are great at quick communication, and I've never had a problem scheduling walks on short notice when I'm in a bind. Overall, everyone I have interacted with at the Company is extremely friendly and are great with my dog. Would definitely recommend! read more

It took me a while to decide if I wanted to leave a public review or not because I respect small businesses but I thought that it was important to share my experience with Windy City Dog Walkers. I interviewed three different companies but really liked WCDW. The staff was friendly, they background check their walkers and they claim to have a thorough training program. I trusted them. When I hired them I told them that door locking was a priority. They assured me that this was standard practice and part of their training protocol. I even reiterated this with my dog walker that they assigned to me. On the first day that he arrived I was alerted from my porch camera that my dog walker was there, so I monitored the interaction. It was day 1 with him so I was checking in. What I saw, was quite upsetting. I'm sure many people don't have porch cameras, so they just might not know what actually goes on. What I saw was that as my dog walker was leaving with my dog, he did not lock my front door. I paid for a 25 minute walk, and the timestamp from the camera showed an 11 minute walk. When he came back, he made no effort to try to unlock the door which meant that he knew that he left it unlocked and did it intentionally. The crazy thing is he didn't leave my house for another 15 minutes. When I turned on my dog camera inside, he wasn't with my dog. Strange all around. This was upsetting so I called the company. It took several hours for the owner to call me back. When he did he made no effort to make the situation right so I fired them. I explained that this was even more upsetting because I now had no one to walk my dog and I had to go to work the next day. They did not offer to send a manager nor did the owner offer to walk my dog until I could find a new dog walker. Had they done that I would have not written this review. Additionally, I was told that they were not going to fire this walker. Rather just shadow him. I understand that people make mistakes. We all do, but intentionally leaving a home unlocked and not fulfilling a service is a problem. If I didn't have a camera I would have never known that my house was left unsecure. I've since found a very reliable dog walking service that I'm beyond happy with. Management is solid and their staff cares. You can message me for a referral. read more

I use Windy City for my dog's weekly walks and I've had nothing but positive experiences. My dog, Rocky, is always happy and well cared for when I get home. All of his walkers have been very sweet and send me cute updates after their visits. The price is also very reasonable. Also, I've never had any issues getting my last minute weekend walks covered. Highly recommend! read more

I've been using Windy City Dog Walkers for over a year now and the service has been TREMENDOUS. Every single walker has taken such great care of my dog. The app is incredibly easy to use and makes it easy to adjust my walk schedule based on my work schedule. Also, they leave the most heartfelt messages each day showing me pics of my precious pup and I know she is in great hands with their walkers. Cannot recommend this service enough! read more

We've been using windy City Dog Walkers for almost 2 years. We love the walkers and they are very friendly and take care of our dog Noodle. They are really good at communication and are always on time. The owner Tony is super nice and he knows what keeps his clients happy. When our walker is on vacation they will find a substitute to walk our dogs. When we need to change our schedule it's easily done via the app. Payment and add new service request can also be done by the app, which makes my life easy! read more

Windy City Dog Walkers - My dog Noodle - Dog Walkers Near Me - Chicago, Illinois

My experience overall has been excellent. Audrey is wonderful with my 11 month old pup -- great communication, very reliable, patient, and professional. I highly recommend Windy City Dog Walkers! read more

They have been so great to work with! Easy scheduling. Making sure I have a consistent dog walker so my dog is comfortable with them. Always make sure to give my dog lots of pets and treats before they leave I know they take good care of my dog! read more

Margo, Tony and Windy City Dog Walkers are the best. We recently moved to Chicago and had to find a new dog walker after having really good experiences with NYC walkers. Windy City Dog Walkers is just as great, if not better! The onboarding process with Tony was extremely thorough and gave me peace of mind that my dog was going to be in great hands. After the initial call, our walker Margo, came over for a quick in-person introduction which I really appreciated. Scheduling and comms occur via their app which is quite easy and intuitive to use. They also have an office team which is available to answer any questions and very quickly responds to scheduling inquiries. I can't say enough about how great Margo is with my dog, Winnie. Winnie can be a bit particular and finicky but Margo fully understands this and watches for her cues. The updates Margo sends after the walk are the highlight of my day and always contain some of the best photos of Winnie I've seen. Overall, Windy City Dog Walkers is extremely professional, reliable and I would recommend to anyone needing a regular dog walker. read more

Windy City Dog Walkers - Dog Walkers Near Me - Chicago, Illinois

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I have Matt walking my dog and he has done an amazing job with her! She was recovering from a surgery and took extra good care of her to help her get strong again. I love the communication, pictures, and strong organization! I never thought we would be using a dog walker but I'm so glad we found them! read more

Omg this company is amazing! When I first got my golden retriever puppy Logan I was super nervous to leave him with walkers when I went to work, but my Fiancé and I are both teachers so our summer had to come to an end at some point.... I had it all planned out, I was going to use Wag/Rover and have a long term sitter. My first sitter got COVID and my second canceled last minute so I was left doing on demand walks which was a real pain. Not ever meeting the person who was going to take care of my dog and having to find a new person each day. Then I switched to Windy City Walkers. There rates were cheaper and I got to meet our Walker, Adam, before ever paying for a walk. Adam and Logan get along beautifully and Adam always sends the best pictures. Probably some of the best pictures of Logan on my phone even though there are thousands that I took!! Over all I really appreciate the walkers that have worked with Logan and the Owner Tony. They are incredibly flexible and always can cover a late night or weekend walk. Please give them a try!!! read more

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Super happy my friend referred me. Ease of booking, great communication and my sitter Jackie is a dream.

I've loved working with the staff from Windy City Dog Walkers! They are extremely professional, responsive, and most importantly to me, they love my pup just as much as I do. My dog is always so excited when his walker comes over, and he looks forward to seeing her. Thank you for taking such good care of my fur baby! read more

Windy City is a great caregiver for our furry loved! They are very responsive, attentive and timely. Emilio has been great to my bulldog, Murphy, as she has had some limitations with the heat this summer. Great service, competitively priced and consistent--couldn't ask for more! read more