Dog Walking Chesterton

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Sitter Profile Image: Sharon & Mark W.
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Sharon & Mark W.
Star Sitter
from
$30
per walk
5.0 out of 5 stars
• 115 reviews
50 repeat clients
40 years of experience
Chesterton, IN, 46304

“Sharon was so amazing with Billie. A true dog whisperer. Billie has never had a dog walker come into the house before and turns out she is quite the guard dog. Sharon had met her at a meet & greet but Billie was scared when she came back alone. But Sharon charmed her with some treats and skritches and her sweet demeanor with animals, and now, after a couple of walks, they are besties. We appreciate Sharon’s extraordinary talent with animals. Her persistence and kindness won over our nervous furbaby and allowed us to be with family during a difficult time. We have already rebooked Sharon and Billie hopes this will be a long-term friendship!”

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Sally W.
Sitter Profile Image: Holly S.
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Holly S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
• 27 reviews
7 repeat clients
15 years of experience
Valparaiso, IN, 46383

About: I've taken care of family pets (cats and dogs) for 15+ years now, and on my own I a have two cats. My schedule is flexible, though my apartment does not allow for dogs and I prefer to pets sit at the pet's home, where they are most comfortable and familiar. I do not have experience caring for pets with serious medical conditions, but I have given dogs their medication on previous jobs. I am currently only available on weekends, though as I transition out of teaching my schedule will open up. I am available for any emergencies over the holidays. My apartment does not allow for dogs, and would prefer not to test how my cats would respond to other animals as it has been just them in my apartment for a few years now. I also believe that it's best to sit for apet in their own home where I am the only thing they have to adjust to. I am fastidious about following owner directions. My cats are fairly low-maintenance, but I also have experience with high-energy dogs like boxers, and pet size does not matter.

Sitter Profile Image: Melanie C.
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Melanie C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
• 82 reviews
32 repeat clients
15 years of experience
Portage, IN, 46368

“This is the first time we’ve used a pet babysitter! Melanie was the perfect fit for our family. Receiving daily pics of Chelsie comforting! Id recommend and use Melanie’s services again!”

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Veronica R.
Sitter Profile Image: Taylor H.
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Taylor H.
from
$15
per walk
1 year of experience
Burns Harbor, IN, 46304

About: I love staying active and spending time outdoors. Your dog and I will have a great time on walks or runs together! And if you have a feline friend, I’m just as happy to relax and keep them company at home. I’m kind of a early morning person so I can take your pet out in the morning for their bathroom breaks walks on a nice afternoon I wake up at 5am to feed my cats breakfast Make sure they have their puzzles filled in the morning and night to keep them Occupied/busy. Clean their litter boxes every morning and before bed .

Sitter Profile Image: Sydney T.
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Sydney T.
from
$20
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
16 years of experience
Valparaiso, IN, 46385

About: Hi there! I worked as kennel staff at an animal hospital for over a year before I moved to Nevada, and then I worked at both and animal hospital and a grooming salon during the two years I lived there! (I have since returned to Northwest Indiana!) I took care of both cats and dogs(of all breeds and disabilities) and helped medicate and treat them! I have owned pets all my life, both cats and dogs, and have been their primary caretakers. I am heavily passionate about animals! I currently have two dogs and four cats. I am 23 and have a driver's license. I love animals more than anything, and would do whatever it takes to make your pets feel happy and safe in my company! I am currently unemployed, so I have plenty of time to take care of other people's pets! I live in a household with other people, so I'm more than able to housesit, as well! I love to keep animals company, and I will do whatever I'm asked to do to take care of someone's pet. If said pet is undergoing training of any sort, I'm willing to make sure that training is implemented throughout the visit, walk, or stay. I absolutely love giving furbabies my attention and love, but will go at the pets pace. I won't force my affections on an anxious animal.

Sitter Profile Image: Elijah G.
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Elijah G.
from
$25
per walk
5.0 out of 5 stars
• 2 reviews
25 years of experience
Valparaiso, IN, 46385

About: We have always had pets (Mostly Dogs) growing up and have never met a dog or cat that didn't like us. We are the type of people that animals (Fur Babies) just feel at ease with. From the smallest of toy and lap dogs to the much larger Great Danes and Mastiffs. We will always get along, even the dog that nobody can handle and scares them. My patients never wears thin and eventually all, even the most stubborn pet warms up to me. Any pet under our supervision will always be taken care of from walks, to alone time to calm their nerves if need be but NEVER neglected. We truly believe that your Dogs and/or Cats should and will be treated just you would. Thanks, Between my wife and I we are essentially available 24/7. And hope to accommodate any ones schedule. Our routine will be scheduled around whatever is needed We have a full half acre completely fenced in (Wooden privacy fence). And of course whatever it is you and your dogs like enjoy we will accommodate.

Sitter Profile Image: Shanie J.
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Shanie J.
from
$22
per walk
5.0 out of 5 stars
• 250 reviews
74 repeat clients
32 years of experience
Valparaiso, IN, 46383

“Shanie is very dependable and my dog is excited when I tell him she is coming. It's comforting knowing I don't worry about him so I can get my work done!”

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Michele M.
Sitter Profile Image: Lora P.
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Lora P.
from
$18
per walk
5.0 out of 5 stars
• 20 reviews
4 repeat clients
10 years of experience
Portage, IN, 46368

“Lora is great with Flynn and I appreciate how reliable and flexible she is!”

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Tanner S.
Sitter Profile Image: Brooklyn T.
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Brooklyn T.
from
$20
per walk
5.0 out of 5 stars
• 4 reviews
3 repeat clients
10 years of experience
Valparaiso, IN, 46383

“Brooklyn has done a great job with my pup. Excellent communication and takes good care of him. She is the first person I’ve used on this app and definitely grateful I got a good person.”

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Alexander T.
Sitter Profile Image: Emily G.
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Emily G.
Star Sitter
from
$35
per walk
5.0 out of 5 stars
• 250 reviews
170 repeat clients
16 years of experience
Michigan City, IN, 46360

“Emily is wonderful dog walker! she really takes the time to make sure my dog feels safe before taking her on fun long walks. She is gentle and very attentive when it comes to watching my fur baby.”

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Valrie J.
Sitter Profile Image: Allie B.
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Allie B.
from
$13
per walk
5.0 out of 5 stars
• 9 reviews
20 years of experience
Gary, IN, 46407

About: My name is Allie, i currently reside in highland Indiana. I recently loss my best friend/other half Black lab "buck". Buck was 13, id do anything to have him back. He taught me so much about love, patience, and appreciation. animals deserve it all and i want to be the to give your friend that too! Im very active, i love taking long walks, trips to the beach, and hike long trails. im also flexible, understanding and very easy to work with . If your dog comes to my home, your dog will be treated like he/she is my own. I have experience with all breeds. Please feel free to reach out with any questions. i love taking pictures and sending updates of your friend throughout the day! Currently my availability is wide open. I go to the gym 4 times a week, but other than that mostly home with my 3 dogs. We have a fenced in yard. Our 2 younger dogs are crated during the day if we're gone. Other than the dogs pretty much have free rein to the coach and to feel at home. Our dogs also eat on a schedule. But we can accommodate your pets needs.

Sitter Profile Image: Joshua R.
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Joshua R.
from
$20
per walk
1 year of experience
East Chicago, IN, 46312

About: I’ve been around dogs since I was a child and owned a few so nothing really intimidates me about any dog or cat. But personally, I do love cats more. They’re just much more my personality. At the moment, I honestly do not have that much time but if I do have an open day, it’ll be on the weekends and I can move things around pretty flexibly Building trust with any living thing takes time and willingness to meet bumps in the road. I’m committed to making sure your pet and your space are well respected and taken care of.

Sitter Profile Image: Addison B.
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Addison B.
from
$25
per walk
5.0 out of 5 stars
• 4 reviews
9 years of experience
Hebron, IN, 46341

About: I have taken care of dogs for many years! I have taken care of my family’s dogs and my friend’s dogs before plenty of times. As of right now in my house hold I have 4 dogs and 2 cats. I adore animals! I love to play with them and walk them! I love watching dogs and I’d love to take care of yours! I love playing with dogs and walking them! I also love meeting different dogs! I would love to care for your animals! I would make sure your dog goes out every couple hours or whenever you need me to let the out. I would feed them, I would clean up there messes if they have any. I would walk them and play with the for you. I would also stay as long as you need me to at your house!

Sitter Profile Image: David R.
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David R.
from
$20
per walk
5.0 out of 5 stars
• 47 reviews
15 repeat clients
18 years of experience
Highland, IN, 46322

“David went above and beyond today. I forgot to update my address in the Rover platform and he went to our old house. As soon as I let him know what happened, he quickly updated the appointment and made his way to our new place. I so appreciate this - my dad is not able to walk my dog and Sam was very happy to see David, since we are repeat customers. I so appreciate his thoughtfulness and care. He is also very attentive and responsive.”

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Mary G.
Sitter Profile Image: Brianna T.
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Brianna T.
from
$40
per walk
5.0 out of 5 stars
• 2 reviews
7 years of experience
Merrillville, IN, 46410

About: I bring 7+ years of pet care experience, including working in a daycare setting where I cared for multiple dogs at once. I focus on safety, structure, fun playtime, and personalized attention to every during alone time. Making sure they feel comfortable, confident, and excited to see me. I am currently completing an externship for school, which takes place earlier in the day. I have open availability after 2pm on weekdays and flexible availability on weekends, making it easy to accommodate walks, drop-ins, and extended care as needed. I prioritize safety, comfort, and routine whether caring for pets in my home or a client’s home. I closely follow feeding schedules, leash guidelines, and any special instructions provided. I maintain clean spaces, supervise all interactions, and communicate updates regularly so pet parents feel confident and at ease.

Sitter Profile Image: Chante S.
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Chante S.
from
$20
per walk
5 years of experience
South Shore, Chicago, IL, 60649

About: I provide dependable, attentive care and treat every dog like family. I’m patient, observant, and make sure each pet feels safe, comfortable, and cared for while their owner is away. I’m experienced with maintaining feeding schedules, walks, playtime, and giving dogs the attention they need to stay relaxed and happy. Pet care fits naturally into my daily routine because I already structure my schedule around being responsible, active, and consistent. I have the flexibility to dedicate time throughout the day for walks, feeding, playtime, bathroom breaks, and giving pets attention and companionship. I enjoy staying active and spending time with animals, so caring for pets feels rewarding rather than stressful. Throughout the week, I make sure pets have a stable routine, plenty of supervision, and a comfortable environment where they can feel safe and relaxed while their owners are away. When caring for pets in my home, I focus on creating a safe, clean, and comfortable environment where they can feel relaxed and cared for. I follow each pet’s normal routine as closely as possible, including feeding schedules, walks, playtime, bathroom breaks, and any special instructions from the owner. I also make sure pets get plenty of attention, supervision, and exercise throughout the day. When caring for pets in a client’s home, I respect their space and maintain the pet’s usual routine to help them feel comfortable while their owner is away. I make sure they are fed on time, walked, given fresh water, and receive companionship and care. I also provide regular updates and photos so owners can feel confident their pets are in good hands.

Sitter Profile Image: Madelynn J.
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Madelynn J.
from
$14
per walk
12 years of experience
Near North Side, Chicago, IL, 60654

About: I help young pets build confidence and good habits through calm, structured training — from creating predictable routines and gentle boundaries to crate comfort, potty consistency, and supervised socialization with all reinforced with positive, steady guidance that makes learning feel safe and fun for every puppy. I work fully remote, so my days are wonderfully flexible and full of time to give your pup attention, play, and comfort. I love having dogs around while I work — it makes the day brighter — and I’m able to adjust my routine to fit whatever your pet needs. Whether it’s weekday walks, daytime care, or weekend boarding, I’m available and happy to help. Your dog becomes part of my daily rhythm, and I make sure they feel seen, loved, and never rushed. I create a warm, safe, and happy environment where pets can relax and feel at home. Because I’m always around during the day, I can give your dog consistent supervision, gentle structure, and plenty of affection. I follow your instructions closely, keep routines steady, and make sure every pup feels secure. My home is calm, clean, and full of kindness — a place where your dog can settle in, enjoy their time, and be treated like family

Sitter Profile Image: Suliee A.
Verified Enhanced Background Check
Suliee A.
from
$30
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
7 years of experience
Homewood, IL, 60430

About: Dog mom that loves to love Furr Babies💕 I have a 1.5 Year old Pup that requires A lot of time and energy, I personally have trained my pup and it has been the best Experience, I have trained puppies since 11 (Yes, 11!!) My love for dogs and Animals has came since a Little girl. I have took care of Puppies as well as Dogs that need Close and careful Care. I promise to treat Your Pet as my own in my care, I hope to hear from you And Your pup😊 I currently work from home so i am home full time dog mommy! I take care and give all my time to my pup Kenzo, We go on walks, Play & Train. Training is an important part of kenzo’s life so i am More than happy to fit your pup in for some training! Kenzo Gets to do whatever he pleases in my home there is not a spot he isnt allowed to play or chill in, i Treat him as a very adored Part of my family so he is use to the good life, your pet will experience that same good life in this home! I am open to Checking on your pup at your home as well, I will just need clear instructions on what it is that you will need done for your or your pet.

Sitter Profile Image: Erin M.
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Erin M.
from
$20
per walk
4.9 out of 5 stars
• 142 reviews
36 repeat clients
25 years of experience
Near West Side, Chicago, IL, 60607

“Erin is easy to work with and is very enthusiastic about our pets. She is especially understanding and willing to put in extra effort to help our shy dog feel comfortable when we’re away.”

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Sara C.
Sitter Profile Image: Isabelle M.
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Isabelle M.
from
$16
per walk
5.0 out of 5 stars
• 8 reviews
3 repeat clients
10 years of experience
Near North Side, Chicago, IL, 60611

“Our Teddy loves his time with Isabelle! He comes back ready for a nap! Isabelle is patient and kind. We couldn’t ask for anything more for our new rescue, as he works on training.”

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Brian F.
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The median cost per walk for dog walking in Chesterton is $20

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How to book dog walking

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Popular requests for dog walking - Chesterton

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Sitters in Chesterton average 3
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FAQs for Dog Walking - Chesterton

Frequently asked questions about Rover

The average cost of Dog Walking in Chesterton is $22 per walk as of October 2026. Most bookings cost between $11 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of October 2026, there are 941 sitters on Rover offering Dog Walking across Chesterton. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Chesterton. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.

The route map lets you review where your dog was walked in Chesterton after the booking. It is not live GPS tracking.

Have specific details you would like included? Message your dog walker in the app before the walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the , which provides up to 25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit .

Yes, you can find walkers who have experience with handling special pet needs in Chesterton. On Rover:

  • 86% of walkers can help with special care needs
  • 93% can help with giving oral medications or injections
  • 97% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .

walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.

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