Show: Gilberto Santa Rosa "When Santa Rosa plays live," writes Peter Margasak, "his band gives him plenty of room. He plays with rhythm, phrasing, and melody like a teppanyaki chef with his knives in the air, slicing and dicing and rearranging: he might use repetition of a single passage to whip up tumultuous tension, lengthen or shorten a line, play against the accent pattern of a song, or clench and loosen his articulation, but no matter what he does it feels effortlessly musical."
8:30 PM, House of Blues, 329 N. Dearborn, 312-923-2000 or 312-559-1212, $53, $48 in advance, 17+.
Dinner: Bijan's Bistro This reincarnation of the venerable late-night hangout Bijan is amazingly unsullied by tourists. Regulars crowd around the gleaming mahogany bar, and Ralf, the courtly host, seems to know half the tables in the joint.
663 N. State St., 312-202-1904
Show: Daughters of the Sun "Minneapolis trio Daughters of the Sun get into some deep territory during their epic psychedelic excursions, but they never seem to get in over their heads," writes Miles Raymer.
9:30 PM, Empty Bottle, 1035 N. Western, 773-276-3600 or 866-468-3401, $5, $3 in advance
Dinner: Crust Chef Michael Altenberg’s casual flatbread-pizza joint, the city’s first certified organic restaurant, is a sleek modern dining hall with bright orange molded plastic chairs and trippy Formica tables; the spacious tented back patio and sidewalk cafe add seats for another 130.
2056 W. Division St., 773-235-5511
Show: Avenue Q Think of it as Sesame Street for grownups, complete with angst-ridden muppets that swear and screw and bouncy, satirical tunes teaching viewers that "Everyone's a Little Bit Racist" and "You Can Be as Loud as the Hell You Want (When You're Makin' Love)."
7:30pm, Bank of America Theatre, 18 W. Monroe St., 312-902-1400
Dinner: La Madia Restaurant in the old Jazz Showcase offering a range of pizzas and a large wine list with 250 by the bottle and multiple options by the glass. As for the pies, they're delicious. A soft, slightly chewy thin crust showcases the pure flavors of fantastic house-made fennel sausage, fresh arugula and prosciutto, and other select toppings like a sweetly savory combo of Taleggio and roasted vin santo grapes that hung in tricky, but ultimately successful balance.
59 W. Grand Ave., 312-329-0400
Show: The Absolute Best Friggin' Time of Your Life Putting up one of the best Second City sketch revues in recent memory takes a perfect storm. First off, you need a cast that can hop easily from deep satire to lighter fare, and from there to rich scenework. And you need a point of view. In the case of the new E.T.C. show, The Absolute Best Friggin' Time of Your Life, it's an overwhelming frustration with the state of our country that's got ensemble members making like Glenn Beck and reflecting on better days.
8pm, Second City E.T.C., Piper's Alley, 1608 N. Wells, 312-337-3992, secondcity.com, $22-$27.
Dinner: Mizu Yakitori & Sushi Lounge Yakitori are a popular Japanese drinking food: skewered and grilled bits of meat, usually chicken. Old Town's Mizu Yakitori & Sushi Lounge takes the concept further, offering vegetable, beef, and seafood skewers as well. And now master chef Seijiro Matsumoto, formerly of the kaiseki restaurant Matsumoto, is on board, offering specials like paper-thin sliced hirame plated to look like a flower, and jellyfish salad with an ume miso sauce in addition to artful sushi.
315 W. North Ave., 312-951-8880