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Timely events, seasonal experiences, and noteworthy happenings taking place across Chicago.

Halloween partygoers in costumes posing with drinks at a decorated Chicago bar.

Nightmare on Kinzie Street: Halloween Bar Crawl in River North — October 31, 2026

Hundred Acre Fortunate Son wine bottle beside a glass of red wine and a plated dish.

Sullivan’s Steakhouse Hosts Hundred Acre Wine Dinner in Naperville

Duckhorn Cabernet Sauvignon bottle and glasses of red wine on a restaurant table

Eddie Merlot’s Duckhorn Wine Pairing Dinner — November 5, 2026

Veronica Beard Gives Back fashion and styling event flyer for November 10, 2026, featuring a model in a blue coat and jeans.

Veronica Beard Gives Back: An Evening of Fall Fashion & Styling in Chicago

Sauce being poured over a plated steak with Hundred Acre wine bottles in the background.

Eddie Merlot’s Hundred Acre Wine Dinner Brings an Exclusive Tasting Experience to Lincolnshire

Hands of different skin tones forming a circle against an American flag background, representing unity.

Of Many, One: An American Tapestry Concert — November 15, 2026

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Our Recommendations

Our most recommended experiences, carefully selected to help you experience the very best of Chicago.

Chicago Architecture Cruise

See Chicago from the river while discovering the architecture and stories that shaped one of the world’s great architectural cities.

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Handmade pasta dish at Monteverde in Chicago’s West Loop

Monteverde

Experience one of Chicago’s standout Italian restaurants, where handmade pasta and bold, modern cooking make Monteverde a West Loop destination.

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West Loop

Explore one of Chicago’s most dynamic neighborhoods, known for destination dining, Fulton Market, nightlife, and a lively urban atmosphere.

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