Dog Walking Jobs in Chicago

Being a dog walker is a highly rewarding job with many exciting challenges.  At Highrise Pet Care, we select dog walkers whom we believe are capable of consistently delivering the high-quality experience that our clients, both pet and human, deserve.

We love dog walkers with experience

We love reaching out to perspective dog walkers who have a track record of success, so we always ask ourselves: Do they have professional experience working with pets? Do they have a customer service background? Our Caregivers communicate with customers on a daily basis, so having customer service skills and pet care experience is essential. Do they appear dedicated? A high grade point average is a helpful indicator that a candidate has focus, but so is a successful background in athletics or the arts.

Chicago’s unpredictable weather

Punctuality is critical because it’s a must-have in the pet care business. We pay close attention to nonverbal cues: did they dress up for the interview? Do they appear enthusiastic and engaged? Additionally, we ask: “Would you be willing to walk dogs for several hours in frigid temperatures?” Nobody loves being in a blizzard, but this way we can evaluate their willingness to go the extra mile, even when the circumstances are tough. We ask this because our Caregivers have to truly love the pets they’re entrusted with. If they don’t, they’ll likely quit first time they’re faced with Chicago’s unpredictable weather. Asking straightforward questions right off the bat efficiently narrows the field of candidates.

Dog walker for a day

If the interview goes well, we then ask the candidate to join us for a full day on the job. Seeing how the potential candidate interacts in the working environment is often more definitive than the traditional interview setting. For example, anyone can tell us that they love animals, but seeing how one of our candidates actually interacts with one is far more valuable to us. We often take this post-interview process one step further and assign the candidate a project with no deadline. If they’re up until 3:00am working on it, we can safely assume that this dedication will remain once they’re hired.

Takeaway Points:

  • We select only qualified and dedicated candidates to interview
  • We ask essential, job-specific questions to make sure they’ll fit in with our business
  • If all goes well, we invite the candidate to join us for a full day in our work environment

Holiday Gift Ideas for Dog Lovers


Furbo Dog Camera: Treat Tossing, HD Wifi Cam, and 2-Way Audio: Toss a treat to your dog through the free Furbo iOS/Android app. HD Camera & Night Vision: Discover your pet’s secret life when you’re not at home. With 720p HD video streaming, a 120° wide-angle view and night vision, Furbo lets you see your entire room, day or night.


Underwater DogsPhotos of dogs are heartwarming and fun, but when the dogs go underwater, look out! Nobody has more fun swimming than a dog. Enjoy all the splashing, sloppy, wet fun in the hardcover book, Underwater Dogs. This 144 page photo collection from Seth Casteel is a great coffee table book for dog lovers of all ages.

The Dogist: Photographic Encounters with 1,000 DogsPhotographed by Elias Weiss Friedman, aka The Dogist, every portrait in the book tells a story and explores the dog’s distinct character and spirit. Themed sections include Puppies, Cones of Shame, Working Dogs, and Dogs in Fancy Outfits, giving every dog lover something to pore over.


ThunderShirt Classic Dog Anxiety JacketThe ThunderShirt design applies gentle, constant pressure to calm anxiety, fear, and over excitement. Calms during fireworks, thunder, separation, travel, vet visits, and much more with no training and no medication so your dog stays drug-free. Great for rescue dogs.


Aikiou Interactive Dog BowlEncourages your dog to eat more slowly, which reduces digestive problems, discomfort and helps prevent weight problems. Manufactured from food grade plastic and is dishwasher safe.


Outward Hound Fun Feeder Dog BowlPromotes fun healthy eating while preventing bloat, regurgitation & canine obesity. Made with high-quality, food-safe ABS plastic that holds up to 4 cups of dry dog food.



Chuckit! Pro LaunchersThrow farther, faster, & never bend down to pick up a slobbery ball again. Made from lightweight flexible plastic that firmly grasps a tennis ball then releases it as you swing. Ergonomic handle for the ultimate comfort & control.


Nylabone Dental Dinosaur Chew ToyDental Chews feature textures that help clean teeth and control plaque and tartar. Bristles raised during chewing help clean teeth and control plaque & tartar build-up. Made for powerful chewers weighing up to 50 pounds!


Outward Hound Hide-A-Squirrel Dog Toys3 squeaky squirrels and durable plush tree trunk. Trunk measures 6″ x 7″ & large squirrels measure 6.5″ from head to end of tail

Dog Walking Safety

Just saying the word “walk” probably excites your dog. As a dog owner, walks can be a soothing start and end to your day, but without the proper training walks can become a dreaded chore.

Walking in Chicago

Your dog may encounter dozens of dogs and hundreds of people while walking in busy neighborhoods like River North, the West Loop or Streeterville. While great for your dog’s mental development, it’s a challenge for you. Your pup has places to go and people to sniff. He will want to pull, but pulling increases the risk of a situation where he’ll become aggressive or fearful.

By keeping him at your side, you dog learns that you’re in control of the walk. The best strategy: stop dead in your tracks or turn around the moment he pulls. When you resume walking, feed him a treat if he stays at your side. If he pulls again, stop and walk the opposite way. Why does this work? He learns that pulling gets him nowhere (literally), while walking at your side gets him treats.

What to Avoid

Steer clear of scenarios your dog reacts negatively to. If your dog doesn’t like skateboards or garbage trucks, it’s best to walk the other way. Trying to acclimate your dog to these items, especially in a busy in a city setting, will be ineffective and increase your pup’s stress levels.

Leashes and Locations

Retractable leashes give your dog more freedom to explore, but they’re not great for training. Use a standard leash while you’re still in the training stage of your pup’s life.

Chicago dogs don’t need extra stimulation. The West Loop, River North, and the Loop offer infinite distractions to a puppy in training. Use an empty dog park or quiet space. If it’s too cold outside, the hallway way of your Highrise building is a good spot. Consistent reinforcement is the quickest way to keep your pup at your side. Start early… you’ll be happy you did!