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Windy City Dog Walkers

4.9 (212 reviews)
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Services - Windy City Dog Walkers

Dog walking

Pet sitting

In-home pet sitting

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Paulina A.

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.

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24 days ago

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11 months ago

Business owner information

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3 years ago

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

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Ask the Community - Windy City Dog Walkers

Review Highlights - Windy City Dog Walkers

It has been a breath of fresh air and stress-free working with Tony, Dustin, Joe, Chris and the rest of the team.

Mentioned in 42 reviews

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City Pets

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I have been very reluctant to write a review on City Pets, perhaps because I feel so sick and…read moreguilty for having taken Cooper here to get groomed just because their rates are less than at Kaiser's (two blocks away) - a good lesson to "buy nice or buy twice". Grooming: I initially took Cooper here for doggie day care since I was working and going to part-time business school. I noticed they offered grooming and decided to try them out since their rate was less than at Kaiser's. The second time I took Cooper for grooming, he came home with such a close shave! Lisa told me they had to take extra fur off since it was matted. I thought it wasn't a big deal until a year later when my husband and I noticed that Cooper's fur was not growing back. We took him to the vet to confirm it wasn't due to a medical reason, and she told us that his fur had been cut down too short that it destroyed his fur follicles. Please see the attached before and after photos. We are distraught that his beautiful fur has not grown back (his neck especially remains bare). Doggie Daycare: The dogs are not given walks during the day. Instead, there are just pee pads on the floor so that the dogs can relieve themselves inside. This can be very counter-intuitive for a puppy who has just learned to be house-trained.

Loved it here, very nice groomer , made my Elvis look super handsome and get lots of compliments…read morealso was very fast took about 1 hour and 30 mins for this haircut meanwhile other groomers were telling me it'll take more than 3 hours . Also affordable $75 plus tip for this specialty poodle haircut

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I needed to get a new pet sitter for my two cats after moving outside the service area of my…read moreprevious pet sitter. I researched a bunch of pet sitters on Yelp and contacted a couple. Stephanie was very responsive and immediately set up an introductory call to get to know my needs and everything about my cats. Stephanie and her team took great care of my cats while we were out of town for a week. The app that Chicago Urban Pets uses allows you to include all the information, and pictures, of your pets. When the sitters come to visit, it lets you know when they have entered your home and after the visit the sitter sends you a detailed report and pictures. It truly allowed us to enjoy our vacation and know that our babies were being very well taken care of. Thank you Stephanie, Abbi, Oliver and Victor!

Chicago Urban Pets Review…read more We called Chicago Urban Pets in advance of our arrival to Chicago. We requested their services for 1 hour with our dog in our hotel room while we would be gone for less than 2 hours. This is what happened. Text message to company: Stephanie, Unfortunately, we aren't very satisfied with the services of the sitters. They arrived late, at 11:00 am, for a one hour visit due to "transport issues." We made it clear we were checking out of the hotel at 12:00 pm. We also made it clear we needed a one hour visit between 9:30-11:30 am. We left at 9:10 am and returned at 11:30 am while the sitters were still present. They said they had just gotten back to the room with Ivy. By our calculations Ivy's walk was very short. Additionally, as a result of the sitters showing up late, Ivy had an accident in the hotel and the hotel is charging us a $250 deep cleaning fee and a $100 annoyance fee. One of the two hours that we were gone was dedicated to your services that we did not fully receive and it also cost us an extra $350. I never want to poorly review any company, especially a locally owned company. But I feel I have no choice in this case. Is there anything I am missing regarding your policies for sitters showing up late? Jodi Watson Text response from company: Hi Jodi I am very sorry to hear about these unforeseen's. Additional costs from the hotel is no one's idea of a good time. Looking over our notes and communications it looks like you had expectations that were different from the nature of our policy and I will make sure Sophie calls you Monday so we can clears things out. Best Stephanie, owner Resolution: I spoke with Sophie on Monday, Jan 30th. The company felt a fair resolution would be to charge us $40 for a 45 minute stay, instead of $48 for a one hour stay, although the sitters were alone with Ivy for 30 minutes. The other 15 (ish) was with us present upon our return to the hotel. Sophie stated the policy is that if you book a sitter from 9:30-11:30, they can arrive at any time between those hours. So, technically, they could have arrived at 11:30 and stayed til 12:30 - even with our hotel check out at 12:00. Had we known this, it would have changed our timing of events and it certainly would have changed who we chose for an agency. The Gwen Hotel recommended we use their Consierge service when choosing a pet agency in the future. We feel this is a good idea.

Windy City Dog Walkers - dogwalkers - Updated July 2026

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