Subway: Red to Grand(312) 527-3510 sullivansteakhouse.com41.889824 -87.629557 415 N Dearborn St (at Hubbard St) River North, Chicago
DinnerAverage main course: $30
You’d think a chain steakhouse would get lost in the shuffle, but this spot distinguishes itself with live jazz and smoke-friendly patio where cigar-puffers head now that they’ve been banished to the outdoors. Though the menu is standard—steaks, chops and seafood are joined by mandatory hearty starters and the usual sides—it’s reliable. Plus, there’s an extensive wine list so you can sip while you work your way through the signature 8-ounce bone-in Kansas City strip.