Wine Tour Guide, Chicago Walking Tours & Tastings
Overview
Lead 90-minute walking tours through downtown Chicago tasting rooms, historic venues, and local spots. You own the guest experience from first hello to final pour, blending wine history, local lore, and safe route management. You join a tight-knit guide team supported by Tourismo and US Ghost Adventures, with training and scheduling flexibility. This role suits storytellers who thrive on live audiences and tip potential $20 to $100+ per tour. You will split time between front-of-house hospitality and on-foot narration, with no two nights alike.
What You'll Do7
- 1Guide groups of up to 15 guests on 90-minute walking tours, weaving wine history, architecture, and neighborhood tales.
- 2Coordinate with partner venues and tasting room staff to ensure seamless entry, seating, and pour timing.
- 3Adapt your route and pacing in real time to manage weather, crowd flow, and safety.
- 4Share tasting notes and regional wine stories that connect each pour to Chicago’s cultural fabric.
- 5Answer guest questions on local dining, nightlife, and off-the-beaten-path spots, boosting their overall trip.
- 6Collect post-tour feedback and tip breakdowns to refine your storytelling and hospitality.
- 7Represent the Urban Wine Walks brand with authenticity and warmth, turning first-timers into repeat guests.
Requirements6
- 121+ years old with valid ID to serve and taste alcohol.
- 22+ years in hospitality, tour guiding, or customer-facing roles.
- 3Ability to walk 2-3 miles comfortably while talking and managing a group.
- 4Strong public speaking voice and comfort with improvisation.
- 5Flexible evening and weekend availability, including holidays.
- 6Knowledge of Chicago neighborhoods, history, or wine is a plus.
Salary Insight
$25k per year
Location
Required Skills
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