Chicago is a drinker’s paradise. Thanks to prohibition over a century ago, illegal bars called speakeasies littered the city, and they’ve never really gone away. You’ll find bars on nearly every corner with outdoor, dive, and upscale bars for every palate and wallet. Whether you’re into craft beers, unique cocktails or rare wines, you won’t regret booking those flights to Chicago. Before you go, you should know that the Windy City is the place to drink, mingle, and bar hop. Just don’t do it all in one night.
Transport yourself to Bavaria with this raucous German-inspired bar. With a jukebox, dancing couples and taps overflowing with German brews, stop by the Lincoln Park neighborhood if you’re looking for an unforgettable experience!
This unimposing dive bar is unmarked and well-loved. Known as either Grayland Pub or Kennedy’s, there’s no denying that it’s a dive: with its cash-only policy, a free-for-all microwave, and its dual name. But it’s a good dive, with great brews.
Karaoke ’till 4 am. Why do you want to know more? Oh yeah – they have complimentary snack baskets and fantastic drinks.
The Violet Hour
Rooted in prohibition-style decor and vibes, The Violet Hour is the place to head if you fancy taking a classy trip back in time. With craft cocktails mixed to perfection and an ambiance as dark and romantic as the city’s gangster past, this spot is well worth the trouble it takes to locate the unmarked entrance.
The Second City
Known as the first ever ongoing improvisational theater troupe in the United States, The Second City is now a popular spot for both sketch shows and improv classes. If you like to laugh, (who doesn’t?!) the live shows at the Lincoln Park Second City won’t disappoint.
Drumbar’s unique cocktail menu boasts a selection of craft drinks, rare spirits, boutique wines, and microbrews. Whether you’re enjoying your drink in the cool comfort of the leather couches inside or admiring the view of the Hancock Center outside, this trendy, prohibition-style spot is a great place to relax.
Scofflaw is located in a cozy corner of Chicago, perfect for a summer night with its great patio scene. Its seasonal cocktails, unique snacks (don’t miss the cheeseboard!) and duck liver plate make it ideal for any party size. It’s good food, good atmosphere, and with good company, makes for a great night.
Three Dots and a Dash
Three Dots mixes traditional cocktails with a Hawaiian flair. Locals love the fresh combinations and the original presentation, as well as the food offerings. Drown your sorrows, or celebrate your success here with the Painkiller – a blend of rum, tangerine, pineapple, coconut, and nutmeg.
Headed out on your flights to Chicago? Let us know where you’ll be going to grab a cocktail!