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  • Loop


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Chicago Theatre Week

Every year, in the coldest depths of the winter, Chicago Theatre Week gives us a great reason to venture outside. The annual event runs from February 16 to 26, taking over stages throughout the city—from major regional hubs like the Goodman Theatre and Broadway in Chicago to intimate spaces such as Redtwist Theatre and Lifeline Theatre. During Chicago Theatre Week, these companies offer tickets priced at $15 or $30 (or sometimes less!). You can browse a complete list of participating shows here, and see our top picks for here.

Winter Wine Walk

Sip on wine while visiting a variety of shops along Southport Avenue (Belmont Avenue to Street) or Roscoe Street (Western Avenue to Damen Avenue). There will be more than 30 different wines, curated by local vendors, to taste and businesses will also provide special discounts on apparel and services during the event. Small bites will be available at some stops.

Chicago Black Restaurant Week

  • Festivals

Chicago Black Restaurant Week returns for its eighth year on February 12. Created by Lauren Smith as a way to highlight and support local Black-owned businesses, the annual event sees participating eateries offer special menus and discounts to diners. This year’s lineup includes CheSa’s Bistro, Bronzeville Soul, Taste 222 and more.

Winter Brew 2023

  • Festivals

Layer up and head to Lincoln Square’s 11th annual Winter Brew, taking place outside along Lincoln Avenue. You’ll have over two dozen local craft beers to choose from, including warm beverages and specialty brews tapped for the occasion. There will also be food available for purchase.

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