The best happy hours in Chicago right now

When the workday is over, there’s no better feeling than kicking back with a colleague over a drink or two. Although Chicago bars only recently offered happy hours due to the change in Illinois state law, the city is home to many watering holes that are perfect for post-work events. These are a few of our favorites, most of which are a stone’s throw from some of the city’s busiest business districts.

The Betty

A West Loop favorite with a retro vibe, the Betty specializes in classic cocktails with a slight twist. Feeling hungry? Their selection of small plates—like a fantastic fried cauliflower—will hold you over until dinnertime.

Broken Shaker

Located inside the lobby of the hip Freehand hotel on the Near North Side, the Broken Shaker is the place to be for craft cocktails, a beachy atmosphere, and a giant Jenga tower.

First Draft

If you’re in the mood for some craft beer, you’ve come to the right spot. This South Loop bar has literally dozens of different beers on tap, so you’ll never be bored with your options. With many TVs lining the walls, sports fans can also rest assured they’ll stay on top of their teams’ progress.

Happy Village

This West Town dive bar is a neighborhood institution. Open since 1964, Happy Village has a relaxed vibe, a number of Ping-Pong tables, and a massive beer garden. Though its food menu is limited, it’s also frequented by a favorite of any hungry Chicago bargoer: Tamale Guy himself.

Maria’s Packaged Goods & Community Bar

Though a bit off the beaten path in the heart of Bridgeport, Maria’s is worth the trek. Once you pass through the liquor store out front, you’ll find yourself in one of the city’s finest neighborhood watering holes—and, odds are, you probably won’t want to leave.

The Matchbox

Just 460 square feet, this River West bar got its name for a good reason—it is positively tiny. But once you’ve managed a spot at the bar, get ready for some of the city’s finest cocktails.

Three Dots and a Dash

This “secret” Near North Side tiki bar is one of the city’s finest places to relax with a beverage in hand—one topped off with a dolphin fashioned out of a banana, to be exact. Here, the mood is tropical and the drinks are strong, so you’ll be ready to hula in no time.


Located in a basement parlor room with a distinct Midwestern log cabin vibe, this Near North Side lounge beneath Pops for Champagne is a refuge from the more touristy fare surrounding it. The bar serves up beers sourced entirely from the Great Lakes region, potent cocktails, and casual finger foods to match.

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