We’ve generally found that people either love Boss Bar or absolutely hate it. Guess which side we fall on? Boss Bar was our home base for a while when it was still a total dive a few years back. And while a recent expansion and makeover has made it nicer than it used to be, the older part is still similar. Boss Bar mainly has the look and feel of a dive in River North, but the fact it’s open until 4-5am every night of the week attracts a lot of different people. You’ll get everything from industry folks, after-work 9-5 people during happy hour, and those shuffling out of Paris Club next door at 3am on the lookout for one more drink that’s inevitably a bad idea.