Five Hidden Gems in Chicago

Effort Required: Drinking and walking can get surprisingly hard…

It’s hardly a hike – you barely cover a half-mile on this walking tour – but beer lovers of all stripes should partake in the Chicago Beer Experience if they want to consider themselves truly seasoned hops hounds. Several bars are included in the tour, where participants eventually sample upwards of sixteen beers as their guide regales them with detailed accounts of the city’s long brewing history, instructs on how to choose proper food pairings (Hint: The answer is bacon…ALWAYS!!!), and even leads the crowd through a short Beer 101 class that covers how this glorious nectar is made. Held most Fridays and Saturdays, rain or shine, the tour includes a cheaper alcohol-free option as well, so you can bring that annoying friend who doesn’t drink beer if you have to (Hint: You don’t). 

Effort Required: Baseball haters still gotta contend with Wrigleyville.

Saying Gingerman Tavern is unknown would be a stretch, but for the non sports-minded who find themselves in jock-heavy Wrigleyville, this place is a sweet diamond in the rough. It’s divey and dusty, to be sure, but the joint touts a hundred beers on its drinks list, as well as pool tables, pinball, vintage arcade games, and a jukebox stocked with a great eclectic mix of punk and indie rock. A famous movie was shot here (read the full review to find out which one) and the vibe almost always trends towards low-key conversation. In other words, leave the fist-pumping at home. 

Effort Required: Resist trying to board one of the yachts.

Although Lincoln Park is one of the best-known parks in the city – and more than worth a visit any chance you can, especially when the sun is out – many overlook the wealth of great views (and romantic opportunities) that await at nearby Montrose Harbor. During the day you will find all sorts here, from grizzled old men fishing off the docks to wealthy yacht owners heading for big cruisers birthed nearby, and everyone in-between. The place all but clears out once night falls, however, and the views south towards the iconic Chicago skyline are some of the best anywhere. Grab a date and head down Montrose Avenue as the sun is setting and you’ll be guaranteed a million dollar vista without having to drop a dime.  

Effort Required: You probably have to drive.

Humboldt Park isn’t lacking in great venues, but it also isn’t lacking in grit, which sadly causes many people to overlook stellar HP spots like Rootstock Wine & Beer Bar. Housed in an unassuming brick building, it’s a simple space inside, with funky scattered furniture seemingly pulled from several random flea markets. The organic food and specialty drinks, however, belie the venue's simplicity as the cocktails are as complicated as they are delicious. The menu can change daily given the emphasis on seasonal and local fare, so you might find grilled octopus one day and grass fed burgers the next. Luckily, their signature bacon toffee dessert is usually available, and you can always find everything from boutique wines to local brews to rare European ciders to wash it all down.

Effort Required: If you’re on a budget, this might hurt a bit…

It’s a bit of a haul from Chicago’s biggest party scenes – and picky eaters will definitely have some trouble here – but Arami in the Ukrainian Village is one of our favorite spots in town to eat legit Japanese food. We haven’t tried, but we’re pretty sure asking for a California Roll would not end well (the staff wield some big knives, and they definitely know how to use them). There’s a small set menu to choose from, but we vastly prefer to let the expert chefs work their way through the daily changing selection of fresh fish, serving up intricately styled bites you definitely won’t have sampled anywhere else. They even put little stones in the soy sauce dishes so that you can’t over-salt your plate, that’s how confident they are in the quality. Thankfully, we’ve never felt the need to disagree. Sadly, we sometimes have to force ourselves to leave early given the rather hefty prices.