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Wine Crawl’s most popular event, the Summer rooftop and terrace series in Chicago returns for the second Summer Session!

The First Crawl Sold Out Completely so we’re duplicating the experience 

Join us as we venture to several new and old favorites as we soak up the sun in Chicago.

The Summer Crawl Features:

Food and Wine Pairings

Prize Giveaways

Both fun and educational for the novice to the experienced food and wine connoisseur


1st Stop the Drumbar rooftop in the Gold Coast neighborhood

2nd Stop W Lakeshore Hotel with views of Lake Michigan and Navy Pier

3rd Stop Aire in the Hyatt Centric in the Loop for beautiful downtown Chicago views


Public Transportation is strongly encouraged. Metered Street Parking Available

The Fine Print

Must be over 21 or over, we cannot accommodate food allergies, No refunds, all sales final unless the organizer cancels the event. Includes 9% amusement tax levied by the City of Chicago.

Traveling to Chicago from Out Of Town?

Book Travel

with our sponsor travel agency

Wine Crawl Calendar


Eventbrite - Wine Crawl Presents The Chicago Summer Food, Wine, and Cocktail CrawlEventbrite - Wine Crawl Presents The Chicago Summer Food, Wine, and Cocktail Crawl