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Show: 30% Chance of Hailey "This is one of the best, most inventive solo productions in years," writes Ryan Hubbard. "Unlike many local comedians, Hailey demonstrates nuanced acting ability, particularly in an antebellum scene in which she pines for her lover. She's got a solid command of verbal and physical comedic skills. (A former gymnast, she flaunts her chops in a parody of floor routines.)"
8pm, iO, 3541 N. Clark St., 773-880-0199, $12
Dinner: Vines on Clark employs two exemplary chefs: Tim Edstrom from Everest and Spiaggia and Raul Ramos from Spiaggia and the Pump Room.
3554 N. Clark St., 773-327-8572
Show: Chicagoland At the start of each show an all-star ensemble creates a tableau onstage, then asks after a blackout, "Where in Chicago did that take place?"
8pm, Annoyance Theatre, 4830 N. Broadway, 773-561-4665, $8
Dinner: Ba Le Sandwich Shop The banh mi (Vietnamese subs) at this modest storefront are pictured and numbered behind the counter for easy reference. Crusty rolls begin with mayo, cilantro, a squirt of fish sauce, jalapeño, and pickled daikon and carrot.
5018 N. Broadway, 773-561-4424
Show: Typeface Justine Nagan, who was named Kartemquin's executive director last year, directs Typeface—a documentary about Two Rivers, Wisconsin's Hamilton Wood Type Museum, the endangered art of letterpress typography, and the resurgence of craft printing.
7:45pm, Gene Siskel Film Center, 164 N. State St., 312-846-2600
Dinner: La Madia Housed in the space where the Jazz Showcase used to be, the restaurant is simultaneously sleek and warm, with a bar up front and a long row of booths lining one wall. A floor-to-ceiling wall of wine provides visual focus. As for the pies, they're delicious.
59 W. Grand Ave., 312-329-0400
Show: Neil Jendon Local guitarist Neil Jendon cofounded Catherine in the late 80s and more recently put in time with ambient psych outfit Zelienople, but over the past few years he's also emerged as a noisenik, playing solo as well as in partnerships both formal and fleeting. The Fortieth Day + Noise Crush headline.
9 PM, Empty Bottle, 1035 N. Western, 773-276-3600 or 866-468-3401, $5, $3 in advance.
Dinner: Rootstock Wine & Beer Bar The main attraction at Humboldt Park's Rootstock Wine & Beer Bar, not surprisingly, is the intriguing list of small-batch beverages put together by a trio of Webster's Wine Bar vets. There are a good many interesting selections—including a passel of wines from Greece, Austria, and unusual spots like Slovenia. One of the best new Chicago restaurants of 2009.
954 N. California Ave., 773-292-1616