Date Ideas for the Chicago Drink Lover
The Chicago drinking scene doesn't just rely on quantity (there is lots of this, though, thanks to the city's array of sports bars, breweries, coffee shops and watering holes). Really, it's about quality, which every Chicago-drinker can attest to. From the city's rich drinking history during Prohibition to its modern day beer and vodka distilleries, Chicago is a great city for drinking (anything). For couples who love to imbibe, here are some suggestions of where to spend your next happy hour.

Speakeasies - easily

historical tour
speakeasy crawl

Do you know how speakeasies got their name? As the legend goes, they were named as such to encourage you to speak quietly about these illegal drinking holes as to not alert the police or neighbors. Speakeasies have a rich history in Chicago where Prohibition was ripe with such establishments and four of the originals continue to operate today. On this tour, you'll have the chance to visit them and hear about their histories while purchasing a few famed drinks here and there.

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Drunk history, or Chicago

pub crawl

Second City has a rich entertainment culture that's second to none in the Midwest, full of improv troupes, nightlife, theater, jazz and more. This tour for two lends you the opportunity to travel and engage with the culture, stopping along the way for appetizers, drinks and more drinks. Discover Chicago's unique history through a sober or tipsy lens - either way, you're sure to have a breezy, relaxed time.

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Shaken, stirred, on the rocks - take this martini making class to discover your preference


Shaken, not stirred. Or perhaps stirred? It all depends on the person. Discover how to make martinis for just about anyone under the tutelage of a professional bartender. You'll learn how to mix and match vodka to concoct some tasty cocktails and leave with a full bottle of vodka. So skip the happy hour crawl and retreat to the comfort of your own home where you can mix the drink of your choice - expertly.

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Beer, bacon - no regrets


Chicago is a sports town and sports towns are known for their excellent bar food. In Chicago, that means local beer and delicious, mouth-watering bacon. Combining two of your favorite guilty pleasures (or two staples in your diet - no judgement), you and your partner will travel to three bars in the North River area to sample the very best of bacon and beer without any regrets of what it will do to your belly.

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Artisan tea tastings for the low-key couple


If your idea of a good date night in involves Netflix and a warm cup of peppermint, you and your date will love a night out trying artisan teas. During this tasting tour, you'll try a variety of unique flavored teas while learning more about the ancient art of tea-making. Perfect for a double date night or a precursor to a night in, you and your fellow low-key partner will dig Adagio Teas' cool vibe and relaxing teas.

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At home brewing: a free how-to

home brewing

A home brewer is legally allowed to craft 100 gallons of wine and/or beer a year; a home brewer couple like yourselves can craft 200 gallons. Do you see where we're going? This free (yes, FREE) craft brewery class sets you up with the home brewing basics and teaches you invaluable knowledge to help you craft your own brews to your preferences. If you're looking for a new project to do together, making and drinking beer is the perfect hobby for you, the beer-loving couple.

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BYOB art class

learn to paint
learn to layer

Have you ever heard of write drunk, edit sober? Well, what about paint drunk, frame it sober? If this (new) adage piques your interest, get ready to paint with a glass of wine/whiskey/beer in hand when you take this BYOB painting class. The perfect way to unwind, get creative and even a little romantic, this class introduces you to painting and brushwork techniques so you can paint something for your better half while you sip on your favorite drink of choice. Win-win.

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From Russia with love, to a Chi-town vodka distillery


Show your local vodka distillery some love by taking this vodka tasting class from the Mid Oak Distillery. Their legendary alcohol is known for its smooth-as-silk quality that has vodka lovers dumping their bigger named brands in favor of their blends. You and your date will sample six different types of vodka and martinis from the menu or sip a flavored vodka for an unusual and unforgettable tasting experience.

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Wine and dine (and never dash.)


Date night usually translates to a wining and dining affair at a fancy restaurant, but real romance is cooking up a meal together at home. If you're hoping to learn how to make fancy food, look no further. Amateur chefs of all levels are welcome to take this cooking class where you'll learn to whip up dishes like sautéed beef tenderloin with crumbled blue cheese, spinach salad with dried cranberries and chocolate whoopie pies. As you prep to dine, wine on two glasses of complimentary vino.

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Tour a local brewery

beer brewing

Fans of local brews are always looking to support their favorites. For fans of Chicago breweries specifically or the brews from Lake Effect, why not tour where the magic happens - for free. Lake Effect Brewing will introduce you to their process of brewing their famous craft brews while you sip, gulp and maybe even chug your tastings for a happy hour, indeed.

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