Best Dog Walkers in Chicago

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


833 West Chicago Avenue, Suite 206, Chicago, IL 60642 Directions

Since 2002

Cat and Pet Care, Overnight Stay, Sitting, Vacation Care, Training Reinforcement, Solo and Group Walks, One on One Care, House Sits & 25-Minute Walks

Windy City Dog Walkers provides dog walking and pet care services in various Chicago communities. WCDW is accredited, bonded, and insured. Their team has committed to the best level of professionalism in pet care. The company gives photos and personalized updates to have customers in the loop during home-stays. Tony Schreck is a licensed dog trainer and walker as a resource for pet care advice. They offer the same dog walker every day. Windy City Dog Walkers offers weeknight, daytime and weekend services to suit any busy lifestyle.

Chicago Reader's Best Dog Walkers Award in 2014

Price: Weekday 10am - 4:30pm: $18 per walk
Weekend 10am - 4:30pm: $21 per walk
Additional Dog $4 per walk

[email protected]


Mon - Fri 9:00 am - 5:00 pm
Sun 12:00 pm - 5:00 pm
Sat Closed

TBR® Inspection Report


2523 West Eastwood Avenue, Chicago, IL 60625 Directions

Since 2009

Individual Walk, 15, 30 and 60 Minutes Walking, Dog Running, 2-Hour Petsit, Puppy Package, Petsitting and Cat Visit, Long Walk & Dog Run

Windy City Paws is a local dog walking and pet sitting in the Chicago area. Their team provides interaction, the most trust service, and most loving care for your pet. They have an office staff of seven supporting around sixty dog walkers and hundreds of customers across the city. Windy City Paws has performed over 250,000 dog walks. They offer a free meet and greet, individualized one-on-one attention, GPS verification, real-time photo visit report, and online scheduling.

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

Price: After 5pm/Weekends:
$30/walk-30 minutes, $48/walk-60 minutes
WCP holidays:
$40/walk-30 minutes
Additional Dog:
$5 for 30 minutes, $10 for 60 minutes

[email protected]


Mon - Fri 8:00 am - 5:00 pm
Sat & Sun Closed

TBR® Inspection Report


2677 North Lincoln Avenue, Chicago, IL 60614 Directions

Since 2010

Pet Sitting, Pet Taxi, Photography, Field Trips, Group and Private Walking, Wedding Escorts, Cat Services, Emergencies

Dogs Deserve It is the leading dog walking and pet sitting company. They celebrate ten years of service to over ten thousand dogs, and four lakhs walks. Their team has extensive training in leash etiquette skills. Lauren Pietrocarlo is using her interactions and public relations experience to make a fresh, professional, accountable aspect to the world of pet care. DDI offers services for 365 days a year. Dogs Deserve It provides pedometers and state of the art GPS walker tracking.

Price: $14 (15 min), $19 (25 min), $26 (40 min), Two 25-minute walks $37 and Two puppy 15-minute walks $28.50

[email protected]


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

TBR® Inspection Report