Dempsey is notoriously difficult to get out of if you’re not the driving type (which you shouldn’t be, not after all these drinks). The resident nightspot of this neck of the woods, Chameleon is where you’ll want to go, should the urge to shake your booty to R&B anthems strike. This space does double duty as an alfresco patio lounge and a shiny futuristic club, so fuel up with bubbly and cocktails like Bourbon Pancakes (maple syrup! $22) and Jamoo (a combo of vodka and coriander, $22) before you bust a move to tunes from resident DJs Titus and Herman.

When the weather is good, eating outside can be a truly enjoyable dining experience. These joints with charming open air areas are just the place to dine on breezy evenings.