WINE AND DINE: Before, after or during your movie, wander in to the Lobby Lounge to sip on some wallet-friendly wine. The South Loop lounge located inside the Showplace Icon Theatre, kicks off their half price wine nights featuring Terrazas Malbec, J Lohr Chardonnay, and Kendall Jackson Riesling. Pair it with the restaurant’s signature pizzas, paninis, and meat and cheese plates. 4-11 p.m., 150 W. Roosevelt Road, $13-15
Get Artsy: Cafe Wha Who's got the "who's who" of visual artists at their monthly Book Club event. Head over to this newish River North coffee and cocktail lounge to meet the artists and get down to the tunes that inspired them to create their pieces. Tonight's soiree features works by photographer Cathy Sunu, followed by graphic designer Nicole Ziegler. 6-10 p.m., 228 W. Chicago Ave.
CHILI WARS: Watch Chicago restaurant chefs such as Stephanie Izard of Top Chef fame duke it out for the title of "Best Chili" and bragging rights at Landmark's Chili Cook-Off and Keg Party. Judge the chili entries for yourself and wash it all down with 25-cent beer. 8:30 p.m., 1633 N. Halsted Street, $20
GET CRUNK: For your late night pleasure-seeking, head over to the Hard Rock Café to party with T-Pain and Jermaine Dupri as they celebrate the one-year anniversary of 107.5 WGCI’s “Tony Sculfield & The Morning Riot” show. Other performances include So So Def recording artist, Dondria, What's Heat LLC. recording artist Hot2Def, and rapper Sean Garrett. 10 p.m.-2 a.m., 63 W. Ontario, $15