Dog Walkers in Chesterton, IN

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Chesterton dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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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
113 reviews
48 repeat clients
40 years of experience
Chesterton, IN, 46304

Sharon and Mark are amazing! When I did my meet and greet with Sharon she was so nice and sweet and made me feel at ease in my decision to use Rover. I needed help walking my 2 golden retrievers due to my work schedule and Rover, Sharon and Mark have been a godsend. I was able to go to work and not have to worry about them. You are notified when they arrive, and after they are finished. They let you know where they walked, what they did and also sent a picture of them. For anyone that is looking to use Rover and is in the area of Sharon and Mark, I HIGHLY recommend them! I am truly grateful for this service and will use them again.

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Heidi M.
Sitter Profile Image: Mary R.
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Mary R.
from
$18
per walk
5.0 out of 5 stars
12 reviews
3 repeat clients
8 years of experience
Chesterton, IN, 46304

She is awesome!! Very punctual, professional and kind. My puppy warmed up to her really quick. So much that she will definitely be missed. I do recommend her, and Yes we will be using her services again if she's available. 🙂

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Om V.
Sitter Profile Image: alexis c.
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alexis c.
from
$20
per walk
4.8 out of 5 stars
50 reviews
20 repeat clients
6 years of experience
portage, IN, 46368

Alexis was absolutely fantastic taking care of my baby Luna! Luna is only 6 months old, has a lot of energy, is not fully trained and I'm sure was a handful for someone to walk in day-one and manage, But she did above and beyond. She brought toys and puzzles, made sure Luna was fed and properly walked. She updated me on how the walks went, when she arrived and left, told me about the other dogs Luna got to meet along the walks and seemed totally joyful and sincere about spending time with my sweet girl. I will be hiring Alexis over and over in the future!

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Raquel W.
Sitter Profile Image: Melanie C.
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Melanie C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
75 reviews
30 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: Julie F.
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Julie F.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
444 reviews
57 repeat clients
17 years of experience
Valparaiso, IN, 46385

Julie was awesome and my pup looked forward to seeing Julie when it was time for her walk. I knew she was in good hands when she was so very excited to meet Julie. Thank you so very much!!!

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Christina T.
Sitter Profile Image: Kortney R.
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Kortney R.
from
$25
per walk
5.0 out of 5 stars
34 reviews
11 repeat clients
14 years of experience
Chesterton, IN, 46304

About: I'll be your pups number one vacation spot! Giving you peace of mind is my number one priority. I love and treat each and every dog like they're my own :) I work from home and have plenty of time for walks and cuddles. I can board dogs on both weekdays and weekends. My schedule is very flexible for walks and/or drop ins. I only board one dog (or two from the same family) at a time so that your dog can have my full attention and have a stress free experience!

Sitter Profile Image: Madelyn O.
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Madelyn O.
from
$21
per walk
5.0 out of 5 stars
21 reviews
6 repeat clients
10 years of experience
Chesterton, IN, 46304

About: Hi there, my name is Madelyn. If we're being honest, I love pets more than most people. I am incredibly passionate about animal care and will absolutely do my very best to make sure your pet stays as happy and healthy as possible. I would be honored to care for your furry companion. I grew up with dogs, and have had cats all of my adult life. I’ve yet to meet a pet that I have not loved with my whole heart. I strongly believe that every dog is special and deserves to be showered with love. If you're interested in booking me, please send me a message and we will work something out! Talk soon! I'm currently working part-time, so I have plenty of time to take care of your pets. I'm available weekdays & weekends, anytime after 11 am. As a dog sitter, I like to keep the environment as close to normal for your dog as possible.. this means I will be happy to go on any dog walking routes around your neighborhood you usually take, and stick to typical feeding times as well.

Sitter Profile Image: Madison E.
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Madison E.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Chesterton, IN, 46304

About: Growing up with many different pets has made me very passionate about their care. I have worked in daycare, boarding, and am a certified dog grooming academy graduate. I opened and own Snout N’ About in Porter, IN. Ask me about adding a grooming during their stay! I am working as a dog groomer with a flexible schedule. Between myself and my partner working from home, we can work together to provide care as needed. I have availability every day. Treating others as you would like to be treated is my lifetime motto. Your fur babies will be given caring treatment as if they were my own.

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
4 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: Jen M.
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Jen M.
from
$20
per walk
5.0 out of 5 stars
30 reviews
5 repeat clients
20 years of experience
Portage, IN, 46368

The best

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Joseph M.
Sitter Profile Image: Skyler V.
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Skyler V.
from
$20
per walk
5.0 out of 5 stars
1 review
2 repeat clients
5 years of experience
Portage, IN, 46368

About: As someone who has grown up with pets of all shapes and sizes from dogs to even a pair of pet rats at one point, I have always loved animals and will take any opportunity to spend more time with them! I have a senior dog named Buddy and a cat named Maple and would love to pour the same love I give to them into your fur babies by playing with them, walking them, and attending to all of their needs. My childhood dog Buddy is also blind, elderly, and diabetic, so I have experience and am very understanding of pets that may need special accommodations and/or medication. Not only do I have experience with the many pets I’ve grown up with and taken care of, but I also have experience working in a pet store and boarding facility taking care of any animals you can imagine. I am currently home for the summer from college and have pretty flexible availability and would love to fill my time taking care of your pets! I promise to give your animals the same love and care I would give to my own pets. I’m excited to keep your pets happy and healthy by walking them, playing with them, snuggling with them, and giving them the undivided attention they deserve.

Sitter Profile Image: Laylani O.
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Laylani O.
from
$20
per walk
5.0 out of 5 stars
1 review
3 years of experience
Valparaiso, IN, 46385

About: I’m currently employed at a local animal hospital, working specifically in the boarding department! Meaning my whole job is to be responsible of 20+ animals at a minimum. I have 3 years of experience, I’ve worked with all kinds of dogs throughout my experience, including sweet, energetic pups, reactive or fearful dogs, strong pullers, and senior dogs who need extra patience and care. I’m comfortable handling dogs with different temperaments and understand how important it is to stay calm, confident, and attentive in every situation. Whether your dog loves long walks and playtime or needs a slower pace, medication, or gentle handling, I always focus on making them feel safe, comfortable, and cared for while keeping owners updated and reassured. I’m pretty flexible! With school i’m mostly not available during the day but weekends and breaks i am happy to stop by and care for pets! I prioritize animal care above all! I am very aware of all animals needs and how i can meet them! I’d be honered to take care!

Sitter Profile Image: Jasmine S.
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Jasmine S.
from
$20
per walk
4.8 out of 5 stars
6 reviews
1 repeat client
10 years of experience
Portage, IN, 46368

About: Me and my husband has had dogs for majority of my life .I had a cocker spaniel growing up and my husband grew up with Akitas as he’s more of the big dog type lol . As of now we have a 6 month old Akita .Shes our world and extremely spoild , so we understand the importance of keeping your dog while you’re gone so he/she won’t feel alone .Also we will give your fur baby the same love and care as we give ours . We are open too watching any kind of dog as long as they are not aggressive !We can schedule a meet & greet before hand to make sure it’s a perfect match .Have any questions just ask ! Thanks in advance.

Sitter Profile Image: Megan R.
Verified Background Check
Megan R.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
42 reviews
12 repeat clients
15 years of experience
Hobart, IN, 46342

Super helpful and engaging!! I love how kind and communicative she is! And my dog loves her. Oreo is a bit crazy sometimes and Megan has the patience and knowledge to redirect her.

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drea h.
Sitter Profile Image: Amy B.
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Amy B.
from
$20
per walk
5.0 out of 5 stars
3 reviews
10 years of experience
Chesterton, IN, 46304

About: I have a long history of dog walking and care experience. I love big dogs that are able to run and be active, however I appriciate small dogs as well! I am a runner so enjoy taking dogs on runs if they are big enough or you are comfortable with that. I like playing with dogs however they feel comfortable, and generally can become a dog’s friend quickly and gain their trust. I know the importance of a dog trusting it’s caregiver/walker in order to create a positive experience for them. I have a job where I can create my own schedule, so have flexibility in when I can walk and dog sit. Dogs truly are great companions and friends and I am excited to be a part of your dog’s well being. I have my own 1 year old golden retriever, and absolutely love spending time with him! I will treat your pets as I do my own, as family! I have my own dog so know the importance of safety and trust. I will make sure your pet is kept safe and comfortable at all times.

Sitter Profile Image: Dylan N.
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Dylan N.
from
$20
per walk
5.0 out of 5 stars
6 reviews
5 years of experience
Valparaiso, IN, 46383

Phenomenal dog walker. Dylan took our dog out on the ice covered sidewalk with no hesitation. She is beyond 5 star!! I feel blessed that we got her and you will too!

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Frank D.
Sitter Profile Image: Madeline B.
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Madeline B.
from
$15
per walk
5.0 out of 5 stars
1 review
1 repeat client
21 years of experience
Valparaiso, IN, 46385

About: I have had pets my entire life and am a mother of three cats. I’ve been pet sitting for my friends since middle school, and volunteering at the Miami-Dade Humane Society has allowed me to socialize and care for cats and dogs with varying needs. No matter what service your pet requires, I’m the one for the job because I will love them like my own! My schedule is very open! I am available super late notice, and will cater to any of your pet’s needs, as well as your schedule. I have three cats and I make sure that they are happy, clean, and fed at all times! They are like my kids! I spend as much time with my pets and others’ pets as possible. I love to go on walks and engage with my animals using lots of toys, treats, and quality time!

Sitter Profile Image: Savannah W.
Verified Enhanced Background Check
Savannah W.
from
$20
per walk
5.0 out of 5 stars
18 reviews
5 repeat clients
10 years of experience
PORTAGE, IN, 46368

About: I have run my own business Holliewood Doo Doo Adventures for 10 years (here in Facebook..check me out). Started out as waste pick up and branched out from there as I got older and it provided flexibility with schedules Also myself and my family have worked with ABRA, Inc Rescue to help foster 3 Dogs to help give them love and Discipline and skills to be able to be adopted out. I enjoy providing the Love, Patience, Time needed for each animal as every personality and needs are different. Also, knowing that they are a part of our families and to help soothe them in the transition as well as fur parents when they need to leave Currently I am a College student and this fits into my schedule well and I have flexibility and that's why I love it. I am now off for the Summer and even though I go back in the fall I work around my online classes. I have 2 dogs of our own and a cat. Realizing they have individual needs and they love the safe space of their own home it is important to me to provide that care that you specifically may need for them. You know this and I have so many that suffer from Anxiety or Seniors that do better in their own homes. That is what I am here for...whether they require so many walks per day or snuggles or play time

Sitter Profile Image: Hailey H.
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Hailey H.
from
$15
per walk
4 years of experience
Valparaiso, IN, 46383

About: I'm a lifelong pet owner with plenty of experience caring for different species of all ages. I'm super comfortable adapting to whatever specific care an animal needs. I am a college student with part-time jobs, which means my schedule is pretty flexible so I can easily adapt my hours to fit any routine and care needs I have two very friendly dogs and one social cat at my own home, so your pet will be in great company. If I'm caring for them at your home, I will follow all given instructions and spend quality time socializing with your pets.

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Over 48
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The median cost per walk for dog walking in Chesterton is $20

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Sitters in Chesterton average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Chesterton on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Chesterton dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 361 dog walkers in Chesterton. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 83% of Chesterton dog walkers respond in under an hour.

Dog walkers in Chesterton have an average of 16 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Chesterton.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 361 dog walkers in Chesterton on Rover, so you’re sure to find the perfect match for your dog! In Chesterton, 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.