The whole team at Windy City Dog Walkers is amazing. You get a dedicated dog walker, and they do a…read morefree 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.

I adopted my puppy, Arthur in June 2025. I saw his picture on the shelter's website and it was love…read moreat 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!

We're so grateful to have found Jerry! He watched our two dogs for a week right after our move to…read moreChicago, and we couldn't have asked for a better experience. The dogs came back calmer, happier, and clearly well cared for. We weren't worried for a second while we were away -- Jerry was incredibly kind, reliable, and accommodating of all their little quirks and routines. Truly gave us peace of mind during a hectic time, and we're so thankful to have someone we trust with our pups. Highly recommend! Attached Nala getting hugs and Simba being a cutie!!

We can't say enough good things about Jerry! He's been so awesome with our 1.5 year old lab mix…read moreRuby and we feel lucky to have found him. I am very particular about who we leave her with and I always know she's in the best hands with him. It's been a great alternative to traditional boarding because Ruby isn't confined to a crate/room and gets ton of love and attention. He's super communicative and flexible with scheduling plus Ruby gets SO excited to see him when we drop her off. He's been very attentive to any specific needs (special diet, medication) and always sends check-ins while we're away. Would highly highly recommend Boy Meets Dog anyone!!

I can't recommend Green Paws enough! The office staff are so helpful, flexible, and responsive, the…read morecare team is so caring, transparent, and thorough - it's been so great to have people I can completely trust take care of our pets while we're at work or away for the weekend. Our pets have lots of needs and everyone has followed our detailed instructions so well. We're moving and we're going to miss everyone at Green Paws so much!

We love Green Paws! They may be a little more expensive than other dog walking businesses, but the…read morelevel of care and attention they provide is unparalleled. They are attentive to detail, responsive, available on short notice in a pinch, and they do so much more. Having an established relationship is great, we always know the pet care specialists and they introduce us any time someone new will be coming around. Excellent service, we recommend them to all our friends

Out-U-Go staff are great with my pups (4) who all have a disability of one type of another. They…read moretreat them like family and I feel confident that they are getting what they need when I am not there! It is very easy to work with them for scheduling and they have been very responsive when I have had to address special or last minute circumstances. I have used Out-U-Go South-loop for 16 years and before that used Out-U-Go Oak Park for several years. Never a problem and highly recommend for both dog walking and pet sitting.

I love this place! They're super dependable, super flexible, super great with my pup and I would…read morerecommend them to anyone. The office staff has been helpful and collaborative. All the walkers have been great; shout out to Ally as her feedback on the visits always make me laugh/smile and she deals well with my diva of a dog. :)

We just had our first Chicago Pet Sitters experience and we are beyond thrilled with their service…read moreand relieved that we found a pet sitting company as detail oriented, friendly, and reliable as they are. We went on a long weekend and Rachel came 3 days in a row to watch our cats. Here's what I loved: An app notification when they arrived The ability to chat with the sitter separately from the admin team A very detailed report of the visit Tons of pictures - not just of the cats but of their water bowls, food bows, and litter box Rachel went above and beyond by bringing some packages up to our apartment - we live in a 4th floor walk-up so that was totally appreciated I have pretty bad anxiety so travel has always been tough because I worry about everything going wrong while I'm gone but that is all out the window because now we've found Chicago Pet Sitters. Not sure how we've survived without them before. A+. 5 stars. 100% recommend.

We have been clients of Chicago Pet Sitters for 3 years now. We moved to a new home recently and…read moretransitioned to a new dog walker for our Corgi Leia. We have always had amazing dog walkers and I have written multiple positive reviews. Kellyn, Leia's current walker, is so amazing too ! I can't say enough wonderful things about her. She does not just take Leia on daily walks, she takes her on adventures!Whether it's to the fire station, to visit other doggie friends, or to make a new friend who happens to be walking by, Leia is in such good hands with Kellyn. Our son even calls her Leia's best friend! Kellyn even filled in and checked in on our 13 yo cat Archie while we were on vacation recently! She does it all!! Many thank to Kellyn and the Chicago Pet Sitters Team for taking such good care of our girl, Leia and kitty, Archie.

My two little doggies have been with DDI for many years and the quality and care they have…read moremaintained throughout the years has been exemplary! Dogs Deserve It, is a professional service. They have back up plans when a walker is out and their website and technology is top notch - I get daily pictures of the pups, a summary of what they did on their walk! Highly recommend DDI! Thanks for taking such good care of my furbabies

We've used this dog walking and pet sitting service for the past 2yrs since getting our pup Wanda…read more Wanda and I really love the service each dog walker brings and the communication from the company and respect of our property is top notch.

My girlfriend and I brought home an 8 week old puppy and knew we'd need a dog walker to join our…read morelittle family once we had to go back to the office. (we were lucky enough to get nearly a month of puppy leave.) It was hard finding someone we felt we could trust, but Jack and his crew came highly recommended from my best friend. And sure enough, as soon as I met Jack I knew he was the one for us. We work in social media so we have weird hours and our schedules change day to day. Jack is always flexible and incredibly accommodating. We literally couldn't raise Theo without him and his team. A BIG plus for us is that Jack and co. only take one dog out at a time, so I know that Theo is safe and getting one on one attention. I know "wag" is a thing, but I see those walkers with 4 dogs at a time and I shudder. What if one dog turns on the other? Also, we love that a quick text and picture is standard and included in the incredibly reasonable pricing. Spencer seems to be the walker who takes Theo out the most, and his pictures are always amazing. We cannot thank this crew enough for taking care of our little guy. It's such a relief knowing we have them in our lives.

I really can't say enough good things about Uptown Pet Services! Jack is such a gem, and I know our…read morecat is in great hands with him. The people who work for him (Spencer, Josh, and any others who I don't know) are also great, and our cat loves them (and she is a VERY picky judge of character!) They're very flexible, have helped us out on very short notice before, and have even helped us out with special requests. I could go on and one, but these folks are the best!

I have a 8 month old puppy who is my baby! I wouldn't trust him to just anyone. I love Green Dog!…read moreThey update you with pictures often. They have great hours and the staff is very friendly. He was recently boarded for a whole week and came back happy and healthy!

Very friendly I am vision impaired, and they helped me to find my Uber when it arrivedread more

Robin and her team are fantastic! Leaving your loved animal for anything can always be stressful…read more When we all went back to into work following COVID, I needed an inexpensivetrustworthy option to walk my pug while I was gone. Robin came in and coordinated a great walker that had also formed a good relationship with my pug, Ted. Robin follows up and even comes in on a crunch during those unexpected times when you just can't bring your dog along. Can't come more recommended!

We've been a happy client for a few years and would 100% recommend this company. They are…read moreresponsive and very accommodating to scheduling needs. Our walker Brendan is absolutely wonderful with our dogs.

Our family has been extremely satisfied with the quality of our regular (and substitute) walker as…read morewell as the responsiveness and professionalism of the administrative team at Windy City Paws. 10/10 recommendation!!

The pet sitters are amazing and extremely diligent about following pet care instructions. They go…read moreabove and beyond for their clients.