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BEST RATED CHICAGO, IL DOG WALKERS

3 Best Dog Walkers in Chicago, IL

Expert-recommended Top 3 Dog Walkers in Chicago, Illinois. All of our dog walkers actually face a rigorous 50-Point Inspection, which includes customer reviews, history, complaints, ratings, satisfaction, trust, cost and general excellence. You deserve only the best!

Windy City Dog Walkers - Chicago, IL Dog Walkers
Windy City Dog Walkers - Chicago, IL Dog Walkers
Windy City Dog Walkers - Chicago, IL Dog Walkers
Best Dog Walkers in Chicago IL - Windy City Dog Walkers video
8+ YEARS IN TBR
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WINDY CITY DOG WALKERS

(5.0 Score)
833 West Chicago Avenue, Suite 206,
Chicago, IL 60642
Directions

Since 2002

Specialty:

✓ Sitting ✓ Vacation Care ✓ Training Reinforcement ✓ Solo Dog Walking ✓ One-on-One Dog Care ✓ Cat and Pet Care ✓ Overnight Stays ✓ House Sits ✓ 25-minute Walking ✓ 45-minute Walking ✓ Poop Pickup Services ✓ Fresh Water and Feeding ✓ Mail Pick-Up Services ✓ Litter Box Cleaning ✓ Petting ✓ Dog Treats ✓ Dog Playing

"Windy City Dog Walkers has over 24 years of experience and offers dog walking and pet care services. Tony Schreck is the owner of the company. He is a licensed dog trainer and walker and is a resource for pet care advice. Windy City Dog Walkers is accredited, licensed, bonded, and insured. The company offers daily dog walks, cat care, and pet sitting, emphasizing personal attention to meet dog walking or pet care needs. They provide one-on-one care for your furry friend and a dog-walking app for iPhone and Android. Their team of pet professionals is caring, reliable, and loyal. All their team members are covered by insurance to protect your pet's security and the safety of your home. Their team has committed to utmost professionalism in pet care.

2026 Update: Windy City Dog Walkers offers daytime, weeknight, and weekend services to fit a busy lifestyle. Dog walks are provided for 25 and 45-minute visits. Cats and other small animals are also provided. Credit card and bank transfer payments are the accepted means of payment."

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Chicago Reader's Best Dog Walkers Award in 2014
License #65685949

Price:

Dog Walking (25 Min) $24.50
Evening $6
Weekend $6
Earlylate $9
Additional Dog $6 Each
Dog Walking (45 Min) $42.50
Evening $10
Weekend $10
Earlylate $15
Additional Dog $10 Each
Vacation Care (Mon–Sun) Per Day $140
Holiday House Sit Per Day $190
Additional Dog Per Day $18
Additional Dog Per Walk $6
Holiday Visit $38.50
Weekday Walks Starts From $24.50
Vcation Care
Monday–Sunday Per Day $140
Holiday House Sit Per Day $190
Additional Dog Per Walk $6
Additional Dog Per Day $18

Contact:

(312) 858-8584

Mon-Fri: 9am - 5pm
Sun: 12pm - 5pm
Sat: Closed

TBR® Inspection Report:

Windy City Paws - Chicago, IL Dog Walkers
Windy City Paws - Chicago, IL Dog Walkers
Windy City Paws - Chicago, IL Dog Walkers
Best Dog Walkers in Chicago IL - Windy City Paws video
8+ YEARS IN TBR
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WINDY CITY PAWS

(4.9 Score)
4809 North Ravenswood Avenue,
Chicago, IL 60640
Directions

Since 2009

Specialty:

✓ Daily Dog Walking ✓ Periodic Dog Walking ✓ Puppy Package ✓ Training Walks ✓ Dog Running ✓ 2-hour Pet Sitting ✓ Feedings ✓ Potty Break ✓ Litter Box Cleaning ✓ Playtime ✓ Shedding ✓ Brushing ✓ Cage Cleaning ✓ Cat and Other Pet Care Services ✓ Cat Sitting Services ✓ Vacation Care ✓ Individual Walks ✓ 30-minute Walking ✓ 60-minute Walking

"Windy City Paws is a locally owned company that was founded by Katie. They are proud to have Fear Free Certified Professionals on their team dedicated to caring for your pet’s emotional and physical well-being. Windy City Paws walkers are well-trained and background-checked. Their team is committed to providing interaction, trustworthy service, and compassionate care for your beloved pet. Their walker hotline allows any dog walker out in the field to call or text a staff member for an immediate response. Windy City Paws offers a free meet and greet, individualized one-on-one attention, GPS verification, real-time photo visit reports, and online scheduling.

2026 Update: Windy City Paws is a professional member of the National Association of Professional Pet Sitters. They are licensed, bonded, and insured. Mastercard, Visa, and American Express are accepted for payments."

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Chicago Reader’s Best Dog Walker Award in 2017-2019

Price:

Daily Walks 30 Minutes $31
Daily Long Walks 60 Minutes $49
Periodic Walks 30 Minutes $41
Periodic Long Walks 60 Minutes $59
Training Walks 30 Minutes $45
Puppy Package Two 15 Min Breaks $45
Dog Run 30 Minutes $45
Petsit 2 Hours $125
Evening (Weekday) Daily Walks $7
Weekend Day 8am–5pm Daily Walks $7
Weekend Evening 5pm+ Daily Walks $14
Additional Pet Daily Walks $6
Holiday Daily Walks $25
Evening (Weekday) Long Walks $12
Weekend Day 8am–5pm Long Walks $12
Weekend Evening 5pm+ Long Walks $24
Additional Pet Long Walks $12
Holiday Long Walks $50

Contact:

(312) 473-6466

Mon-Fri: 8am - 5pm
Sat & Sun: Closed

TBR® Inspection Report:

Dogs Deserve It - Chicago, IL Dog Walkers
Dogs Deserve It - Chicago, IL Dog Walkers
Dogs Deserve It - Chicago, IL Dog Walkers
Best Dog Walkers in Chicago IL - Dogs Deserve It video
6+ YEARS IN TBR
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DOGS DESERVE IT

(4.9 Score)
1300 West Belmont Avenue,
Chicago, IL 60657
Directions

Since 2009

Specialty:

✓ Group and Private Dog Walking ✓ Field Trips ✓ Wedding Escorts ✓ Cat Services ✓ Pet Sitting Services ✓ Pet Taxi Services ✓ Photography

"Dogs Deserve It is owned and operated by Lauren Pietrocarlo. Their dog walkers have comprehensive training in DDI leash etiquette® skills. They implement simple and easy techniques so that your dog will walk better on the leash. All of their techniques are force-free and may involve the use of specific leashes and collars. They are also proud to partner with Nest, an indoor security camera used for child or dog monitoring. They believe that Nest is a natural addition to their dog walker tracking services. They also provide Musher's Secret Paw Wax to all clients free of charge. Dogs Deserve It is a proud member of the Pet Industry Coalition, an organization that requires 100% legal compliance in all operations.

2026 Update: Dogs Deserve It has over 10 years of dog walking service for more than 10,000 dogs, with the completion of over 400,000 walks."

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Price:

Dog Walking 15 Minutes $23
Dog Walking 25 Minutes $29
Dog Walking 40 Minutes $37
Two 25 Min Puppy Walks Per Walk $30
Two 15 Min Puppy Walks Per Walk $24
As Needed Walk 15 Minutes $28
As Needed Walk 25 Minutes $35
As Needed Walk 40 Minutes $45
Morning Evening Weekend Walk Fee $6
Additional Dog Per Dog $5
Plant Watering Service Per Day $14
Puppy Walk 15 Minutes $24
Puppy Walk 25 Minutes $30
Pet Sitting Per Day $135
Hourly Pet Sitting Per Hour $40
Holiday Pet Sitting Per Day $180
Additional Dog Petsit Per Day $8
Critter Sitting Per Day $26.50
Fish Visit Per Visit $16
Pet Taxi One Way $35
Pet Taxi Round Trip Per Hour $55
Pet Taxi Waiting Fee 20 Minutes $10
Pet Photography 60 Minute Session $100

Contact:

(773) 524-7128 (773) 573-8216

Mon-Sun: 8:30am - 5:30pm

TBR® Inspection Report:

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WINDY CITY DOG WALKERS REVIEWS

Windy City Dog Walkers is the best dog walking service!! My walker is always on time and very attentive with my puppy and making sure she gets a good amount of exercise and interaction with other dogs. I always appreciate the comprehensive post walk summary and good communication for logistics. I highly recommend Windy City Dog Walkers!

We have had a great experience so far with Windy City Walkers. Several of our neighbors use them and so they were the obvious choice for us. Our walker, Jackie, always takes great care of our pug. Scheduling is easy, and they are flexible and responsive.

Has been an excellent experience so far. Our dogwalker Julia is wonderful and our adore her. She’s prompt and reliable, and a great communicator. The business is also very responsive and organized and they portal is easy to use.

These reviews are provided for information purposes and to help you make informed decisions.

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WINDY CITY PAWS REVIEWS

Windy City Paws has been wonderful. I love that they care about my dogs and maintain consistency and professionalism. We are very fortunate to have Sarah M as our dog walker; she has gone above and beyond with my dogs. She keeps tabs on how they are doing, notes any notably different behavior, and makes thoughtful suggestions and route optimizations so that the dogs can have their best walk. I feel like she has a special connection with my dogs, and I really enjoy reading about the adventures they have together. I have high trust in her care of my dogs. Sarah is also clear with her communication and arrives at a consistent time, which makes planning so much easier. Our dogs have also gotten a lot better at walking. Thank you so much, Sarah!!

Windy City Paws has been amazing and our walker Cai has been absolutely fantastic with our pup, even helping manage his dog reactivity. Our dog is always excited for a walk and their communication has been fantastic. Easy to recommend and trust.

We worked with Windy City Paws three-days a week for several years with our dog Chickadee, who recently passed away. Windy City Paws was great. Very reliable and always provided good care.

DOGS DESERVE IT REVIEWS

Rachel at Dogs Deserve It has been the best dog walker we could have asked for. Our Cattle dog, Toni, is a tough dog to walk as she is very apprehensive with new people and doesn’t warm up to strangers very easily. Rachel was amazingly patient with her and took the time to build a relationship before taking her on walks. Toni came to love Rachel the same way she does us, which is no easy feat! We know that our dog is in good hands every time she is with Rachel. Rachel even takes the time to avoid other people on walks and gives Toni her space when she needs it. I can’t express how lucky we are to have found Dogs Deserve It and to have found Rachel. Thank you so much!

We have had the best experience with 2 walkers with Dogs Deserve It: Naomi and Jack! We moved from one neighborhood to another which is why we had to switch but our pup Finnegan has absolutely adored them both! On top of an easy to use app for scheduling, minimum 2 pics updates per walks, and super competitive prices, Dogs Deserve It is hard to beat!!!

I just used DDI for the first time while away on vacation and will definitely be using their services again! Corbin did a great job looking out for my two kittens for check ins

TBR® Inspection Score Report

WINDY CITY DOG WALKERS Total Inspection Points: 119/120
Experience: 9
Acknowledgments: 10
Business Images: 10
Complete Info: 10
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Legitimate Ratings: 10
Location Proximity: 10
Pricing: 10
Reviews Accuracy of : 10
Website Standard: 10

TBR® Inspection Score Report

WINDY CITY PAWS Total Inspection Points: 118/120
Business Hours: 8
Acknowledgments: 10
Business Images: 10
Complete Info: 10
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Legitimate Ratings: 10
Location Proximity: 10
Pricing: 10
Reviews Accuracy of : 10
Website Standard: 10

TBR® Inspection Score Report

DOGS DESERVE IT Total Inspection Points: 117/120
Experience: 9
Reviews Study: 9
Social Media: 9
Acknowledgments: 10
Business Hours: 10
Business Images: 10
Complete Info: 10
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Legitimate Ratings: 10
Reviews Accuracy of : 10