The Loop is not a weekend hot spot. If you're there on a Saturday, it's probably because you're stuck at work or seeing a play. But it is an after-work hot spot, particularly on Friday evenings when it's nice outside. Why travel far to get drinks with your co-workers and friends when you can do it close to the office?
From dive bars to the slightly more sophisticated, these are the best places to grab drinks in the Loop after work.
If you work remotely close to Monk's and have never been, then you're doing life all wrong. The place has been around since the 70's, and is always busy starting at 5pm during the week. It's designed to resemble a monastery, and who doesn't want to drink in a religious space? Plus, free peanuts, and you can throw the shells on the ground. Nothing is more fun than being allowed to make a mess.
A rooftop open year-round is a good way to get people in the door, and that's why Plymouth is a solid place to hang out and drink. There's often an influx of law students from John Marshall and DePaul on a nice day, so be prepared to have to stake out some space.
Miller's has been open for over 80 years and feels like it's from another era. It's old school - with a huge bar, big booths, and a friendly staff encouraging you to have a drink at any hour of the day. Dirty martini at 8am? That used to be the norm here. Morning drinking is more frowned upon in the 21st century, but you'd be smart to pop in after work.
Exchequer is cut from the same cloth as Miller's, which makes sense considering it's been around a while and they are neighbors. But head to Exchequer when deep dish pizza sounds like a good idea to pair with an after-work cocktail or two. Hopefully you don't have plans for later at night.
Stocks and Blondes both sounds and looks like the dirty basement bar you frequented in college. It's like Rick’s in Ann Arbor, Kollege Klub in Madison, Kilroy's in Bloomington, or whatever your version of that is. And that’s why we like Stocks and Blondes for an after-work drink. Even if you're too old to fully live like a college kid, you're never too old to throw back a few beers in a dingy bar.
When you're trapped in the cubes all week, a little fresh air will do you some good. That's why you should flock to South Branch Tavern the second it's nice outside. The huge patio area right on the river is the perfect place to contemplate the fact that you have no idea what you're doing with your life.
The name Poag Mahone's comes from a Gaelic saying that basically means "kiss my ass." With a name like that, you know it's a good place to drink. The burgers are solid, too.
Do you want your post-work happy hour to be a drinks and oysters happy hour? Hit Pearl's Tavern if you have a smaller group that's looking to snack on shellfish to go along with your drinks. Cocktails always make the monotony of the week a little brighter, and oysters only double the fun.
When traders at the CBOE and CBOT aren't busy getting rich off market volatility that hurts your 401K, they're grabbing a meal or drinks at Ceres' Cafe. And we suggest you join them. Order something basic like a jack and coke or sprite and vodka, mostly because you'll get a giant cup of just alcohol and a can of soda on the side. The patio is awesome in the summer.
Check out the Gage if you need to entertain clients or generally want something a little more sophisticated. Yes, it's a restaurant, but it also has a great bar area where you can post up for a while. Get yourself a scotch egg and a dark beer to go with it.
Want to do something real fun? Head to what's technically the South Loop to Buddy Guy's Legends, opened and named after Buddy Guy, the famous blues musician. Catch some live music to go along with your drinks, because lord knows that's better than listening to Gene from accounting take the mic at karaoke. Buddy himself even takes the stage in January.