Dog Walking Chesterton

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

End
Search

Over 7
pet parents in Chesterton have booked dog walking

Chesterton, Find top rated dog walking

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

1 / 1
Sitter Profile Image: Holly S.
Verified Enhanced Background Check
Holly S.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
15 reviews
4 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.
Verified Enhanced Background Check
Melanie C.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
79 reviews
31 repeat clients
15 years of experience
Portage, IN, 46368

Melanie was great! She was on-time and have our pups a great, long walk each booking. Ralphie was a little hesitant with her the first walk, but once she picked up his leash he was excited. After that I think they were besties. We got pictures each walk also which was fantastic!

Profile image
Rachel R.
Sitter Profile Image: Skyler V.
Verified Enhanced Background Check
Skyler V.
Star Sitter
from
$29
per walk
5.0 out of 5 stars
8 reviews
5 repeat clients
5 years of experience
Portage, IN, 46368

Skyler has been very reliable and trustworthy with my pup! Always shows up on time and responds quickly to communication! Would definitely recommend!

Profile image
Julia B.
Sitter Profile Image: Aubrey R.
Verified Background Check
Aubrey R.
from
$20
per walk
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Chesterton, IN, 46304

About: I’m new to Rover, but a lifelong dog lover. My first best friend was a yellow Lab named Candy, who slept at the foot of my bed every night. Today, I share my life with two Chesapeake Bay Retrievers who are truly my fur babies. I’m a mom to two teenage daughters and a small business owner in Chesterton. I’m very active and regularly take my own dogs on long walks and runs at Coffee Creek, so I’m happy to walk, jog, or play with your pup—or stop by for cuddles and treats while you’re at work. I’ve volunteered with animal shelters over the years and am pet CPR certified, so your dog will always be in caring, capable hands! Im a small business owner that is primarily weekend based, this leaves me a flexible weekday schedule that allows me to give your pets reliable exercise and attentive care and on a regular basis if needed. I am happy to check in with your dogs or cats, feed, cuddle and give them anything needed during a visit. I’m responsible and mature.

Sitter Profile Image: Julie F.
Verified Enhanced Background Check
Julie F.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
479 reviews
60 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!!!

Profile image
Christina T.
Sitter Profile Image: Sharon & Mark W.
Verified Background Check
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 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!

Profile image
Sally W.
Sitter Profile Image: Laylani O.
Verified Enhanced Background Check
Laylani O.
from
$20
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
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: Jen M.
Verified Enhanced Background Check
Jen M.
from
$20
per walk
5.0 out of 5 stars
31 reviews
5 repeat clients
20 years of experience
Portage, IN, 46368

Worth it just for the picture 😆

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

“Megan was fantastic! She was very polite, knowledgeable about dogs, and really listened to all my needs and concerns. We truly appreciated her punctuality—it made my surgery week a bit easier and less stressful.”

Profile image
Summer F.
Sitter Profile Image: Mary R.
Verified Background Check
Mary R.
from
$18
per walk
5.0 out of 5 stars
13 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. 🙂

Profile image
Om V.
Sitter Profile Image: Shanie J.
Verified Background Check
Shanie J.
from
$22
per walk
5.0 out of 5 stars
243 reviews
73 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!

Profile image
Michele M.
Sitter Profile Image: Ella V.
Verified Enhanced Background Check
Ella V.
from
$25
per walk
5.0 out of 5 stars
4 reviews
7 years of experience
Valparaiso, IN, 46383

About: I have taken care of various breeds and ages of dogs since I was 13. Family, neighbors, and work friends have depended on me to watch their dogs. If there are other animals besides dogs, I will take great care of those as well. I am currently in college full time and unemployed. I will definitely have time to work my schedule around the times you need, I am always free on Monday, Wednesday, and Friday-Sunday. I do not offer services where your animal will come to my home, I have 2 dogs who aren’t fond of others. I will absolutely come to your home and take care of your dogs as many times as needed. Walks, potty breaks, breakfast/dinner, I do it all.

Sitter Profile Image: alexis c.
Verified Enhanced Background Check
alexis c.
from
$20
per walk
4.8 out of 5 stars
51 reviews
22 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!

Profile image
Raquel W.
Sitter Profile Image: Taylor H.
Verified Enhanced Background Check
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: Madelyn O.
Verified Background Check
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: Sylvia R.
Verified Enhanced Background Check
Sylvia R.
from
$20
per walk
10 years of experience
Chesterton, IN, 46304

About: I have had extensive experience within the environment of animal care. I have been involved in places that include animal shelters and even animal hospitals, and strive to put forth my best care that involves your fur babies! Afternoons/evenings work best for my schedule, but I can always work around yours to fit your needs the best! Right now, my schedule is very flexible! Even though I do not offer the option of boarding, I will strive to make your pet's safety my number one priority when I am walking them!

Sitter Profile Image: Kortney R.
Verified Enhanced Background Check
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: 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: Madison E.
Verified Enhanced Background Check
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: Amy B.
Verified Enhanced Background Check
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.

1 / 1
View more

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

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local walkers who will treat your dogs like family

  1. 1. Search

    Browse profiles of walkers near you who offer dog walking
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for dog walking - Chesterton

Select a filter and find qualifying sitters offering dog walking.

Sitters in Chesterton average 3
repeat dog walking clients

FAQs for Dog Walking - Chesterton

Frequently asked questions about Rover

The average cost for Dog Walking in Chesterton on Rover is $21.4 per walk (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of July 2026, there are 1,084 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 services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Chesterton.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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 Rover Guarantee , 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 Rover's Trust & Safety page .

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

  • 95% of walkers can help with special care needs
  • 94% can help with giving oral medications or injections
  • 100% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge