02 / COMPARE PUBLISHED OPTIONSThree Chicago dog-walking options, side by side.
Start with the visit and schedule that fit your dog. These durations and conditions differ, so the lowest headline price is not necessarily the best fit.
Public provider pages checked October 30, 2026. We verified the published information below, not care quality, insurance, or current openings. These are editorial listings; no booking partnership is claimed.
Windy City Paws
$31 / 30 minutes
Recurring walks: at least 3 fixed weekdays per week, during weekday daytime hours.
Individual neighborhood walks. Occasional walks have a different rate.
Confirm your address directly.
Check provider rates & details ↗Windy City Dog Walkers
From $24.50 / 25 minutes
Advertised weekday starting rate. Confirm your schedule and total price.
Private walks; provider advertises a consistent walker.
Published areas include Lincoln Park, Lakeview, Logan Square, West Loop, and South Loop; confirm exact address.
Check provider rates & details ↗Dogs Deserve It
$31 / 25 minutes
Recurring package: at least 3 days per week, weekday daytime; 2-hour arrival window.
GPS tracking and photo updates. As-needed visits cost more.
Published areas include Lincoln Park, Lakeview, Logan Square, Bucktown, and Wicker Park; confirm exact address.
Check provider rates & details ↗Before booking, confirm your address, arrival window, walker continuity, backup coverage, insurance, cancellation terms, and the full cost including extra dogs, evenings, weekends, and holidays. Rates can change. Contact providers directly for urgent care.
03 / START WITH THE ESSENTIALSA little clarity goes a long way.
01Start with your neighborhood
A great service is only useful if it covers your home and preferred walking window.
02Compare the whole visit
Ask how much time is spent walking, how updates work, and whether visits are private or shared.
03Check the care plan
Discuss access, backup coverage, insurance, emergency procedures, and your dog’s needs directly with a provider.
04 / YOUR NEXT STEPYour dog-walker comparison worksheet
Compare your shortlist, weekly costs, coverage, and care requirements. Download the worksheet free; no email required.
Download free worksheet - Neighborhood and recurring schedule
- Private or group visits and actual visit duration
- Consistent walker and backup arrangements
- Insurance, references, and emergency process
- Cancellation rules, extra dog fees, and holiday costs
Privacy for this inquiry page
When you submit an inquiry, Chicago Dog Service stores your name, email, optional phone, neighborhood, care type, timing, frequency, number of dogs, preferred days and time window, visit length, optional start date and budget, message, contact permission, optional marketing preference, and basic source information in a private Cloudflare database so we can manage and respond to your request. A short-lived hashed network identifier helps limit spam; raw IP addresses are not stored in the inquiry record. Cloudflare Web Analytics measures site visits and page performance without advertising cookies. Hosting providers may retain routine access logs. We do not sell inquiry information. We will ask your permission before sharing your contact information with a provider. We send an inquiry acknowledgment and an internal notification through Google Workspace. Marketing updates require your separate optional checkbox; marketing follow-up sequences are not active. To request access, correction, deletion, or withdrawal of marketing permission, email [email protected]. Please do not submit payment details or sensitive personal information.