Headquarters Beercade

Trying to decide whether to go out to the bar or stay at home to play video games? Why not do both at Headquarters Beercade. This Lakeview-area funhouse offers 37 vintage arcade games for your enjoyment, as well as a menu full of game-inspired cocktails, a healthy selection of beers — over a dozen on tap as well as a selection of bottles and cans — and a reasonable stock of spirits for those who like their liquor straight. Better yet, the HQ just opened a 7,000 square-foot pinball alley expansion that's host to over 20 pinball games both new and old. Just don't forget to bring quarters — you're going to need them.

The Drawing Room

We're not usually ones to recommend sitting at a table if you come to a place for drinks — the bar is normally the way to go — but the table service at The Drawing Room is special enough to make us consider it. This intimate underground lounge/restaurant offers up outstanding food, but its drinks are even more noteworthy. If ordered form the table, a bartender will arrive with a cart, explaining the ingredients and history of your drink while preparing it on-site. And should you not find anything you like on the cocktail list, the skilled mixologists are more than capable of crafting a drink to suit your tastes. Clean restrooms and superb service round out the experience; reservations recommended.

Bar Toma

Opening a new restaurant is difficult anywhere. Opening a new pizzeria in a town known for the stuff is nearly insane. Yet that's the challenge Chef Tony Mantuano took on — and met — when he launched Bar Toma last year. With over 20 varieties of pizza baked in a wood-fired oven, this neighborhood-style spot doesn't mess around on the pie, and backs it up with a mozzarella bar, a range of cold and hot antipasto, over 60 wine selections, gelato, an espresso bar, and even a gluten-free menu — which, unfortunately, doesn't include pizza.

Just For Laughs

It doesn't matter if times are good or times are bad — we can always use a good laugh. And you'll find plenty of them at the Just For Laughs festival. Slated for June 11-16 at Park West, The Chicago Theatre, and The Vic Theatre, this festival of funny will play host to a number of comedians, including Seth Meyers, David Cross, John Hodgman, Artie Lange, Bob Newhart, and, to cap things off, HBO's own Bill Maher. Tickets are on sale now, so grab 'em up before they're gone.

Marie's Riptide Lounge

High class cocktails? Craft beers? Small plates of immaculately-prepared food? You won't find any of those things here. What you will find at Marie's Riptide Lounge is a lively crowd, a killer old-school jukebox, cheap drinks, karaoke, holiday decorations, and, depending on what time you arrive, plenty of drunk people. This time capsule of a dive is open irresponsibly late — until 5am on Saturdays — and is a perfect place to finish off the night should your prior drinking establishment of choice declare last call before you're ready.

The Butcher & Larder

Sustainability isn't as easy as it sounds — just ask the crew at The Butcher & Larder. With the goal of becoming the Windy City's first sustainable, all whole animal butcher shop, they source their animals from small, Midwestern family farms, and custom cut the meat themselves. In addition to traditional cuts, they also make a number of sausages, patés, and deli items like ham, bacon, and corned beef. Looking to learn more about the craft? They offer butchering and charcuterie classes — sharing their CIA-gained knowledge — and have plans to hold occasional family-style dinners at the shop.

The Bedford

Some bars are underground. Some are housed in former banks. Some even have quiet lounges, separate from the (slightly) more rowdy bar. The Bedford has all three. This Wicker Park spot sits under the ground in a former place of finance, and offers a large, well-lit bar, a cozy lounge that's literally inside the old vault — you pass by the heist movie-like door to enter — and lined with old safety deposit slots, and a small dining room for those that are looking to consume more than just booze. No matter why you're there, plan on spending some time soaking up the ambiance while you sip on one of the signature cocktails, a glass of wine, or one of the small selection of refreshing beers.

Saint Alfred

If you're looking for a new pair of kicks, it's hard to go wrong with a trip to Saint Alfred. This Wicker Park shop stocks all the hard-to-find kicks from Nike, Adidas, Converse, and Reebok that you'd expect, but also sports an impressive collection of lesser-known brands. In addition, it also stocks a nice selection of clothing and accessories, including shirts, hats, bags, and other essentials, many of which are self-branded. And don't worry should all that shoe shopping leave you thirsty — you're just a few steps away from excellent refreshments at The Violet Hour.

The Signature Room at the 95th

Do you want great food, or stunning views? Luckily, you don't have to choose at The Signature Room at the 95th. Located on the 95th floor of the John Hancock Center, this upscale eatery offers 360º views of the city and refined New American cuisine. While we definitely recommend hitting up dinner, which boasts dishes like a pan seared veal chop, a Wagyu filet, and chorizo-stuffed pork chop, the lounge is just one floor up in case you'd rather enjoy a high-altitude libation.

This post is brought to you by our friends at Cadillac.

Baconfest Chicago

It doesn't start for a little over a month, but we wanted to tell you about Baconfest Chicago well in advance so you can get your travel plans in order. This fantastic event celebrates everyone's favorite cured meat with a huge roster of restaurants serving both lunch and dinner sessions of their own takes on the theme of bacon, with everything from bacon scones and bacon-wrapped bratwurst to bacon pizza, bacon tacos, and even a bacon bloody mary. Separate events are planned for San Francisco and Washington, D.C., but if you want to enjoy the original, you'd best find yourself in the Windy City on April 20.

Haberdash EDC

Longtime Uncrate readers likely know the meaning behind the acronym EDC, but these fine folks have expanded it further. While it does offer Every Day Carry products, Haberdash EDC now offers every day casual sportswear and footwear as well. Recently expanded to downstairs, the shop offers only the highest-quality clothes, accessories, and apothecary from brands like Baxter, Nike, Aesop, Baldwin, Filson, and Woolrich, and if you stop by Tuesday through Saturday, you can even enjoy a hot shave. Need something a bit more formal? Stop by Haberdash Bespoke, which is just a couple doors down.

The Old Town Ale House

When someone calls a bar the best in the world, you take notice — and when that person is as well traveled as Roger Ebert, it carries even more weight. Despite the high praise, however, The Old Town Ale House isn't known for its fantastic cocktails, or its great beer selection. Instead, this classic dive bar is all about atmosphere. Risque paintings of politicians in various states of undress line the walls, created by regular Bruce Elliott. A funky smell lingers. The drinks are cheap. With a history that dates back to the '50s and regulars that have been drinking there for nearly as long, it's an experience not to be missed — and it's location directly across from the Second City doesn't hurt, either.