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Windy City Dog Walkers

West Town

About

Solo walks from $24.50 for 25 minutes and overnight house sitting at $140 a day for existing clients. Its walkers are independent contractors.

Services

Walking

Windy City Dog Walkers has walked dogs in Chicago since 2002, from an office on Chicago Avenue.

Walks are solo; the company says it does not group-walk. Weekday walks start at $24.50 for 25 minutes. Its full rate table sits in a widget that could not be read, so only the starting price is given here.

House sitting is $140 a day, covering eight hours overnight and three 25-minute walks, plus $18 a day for each extra dog. It is offered only to clients with at least one weekly walk who have been with the company for 30 days or more.

One thing this company says that most do not: its walkers are independent contractors, with only managers on staff. It says applicants are screened for criminal records and that the company is licensed, bonded and insured. Report cards with photos come through its app.

Good to Know
Prices and terms from the company's own site, read 2026-10-13. House sitting is for existing clients only: one weekly walk and 30+ days as a client. Walkers are 1099 independent contractors, per the company's FAQ. The company lists its neighborhoods 'and more'.

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Location & Contact

833 W. Chicago Ave., Suite 206, Chicago, IL 60642

Location

Serves
Andersonville Lincoln Square Lakeview Logan Square Lincoln Park Bucktown Wicker Park River North West Loop

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