Chicago Bars Guide
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Drinking in the Culture in Chicago – Essential Chicago Bar Guide

There are many things I’d associate with Chicago prior to my visit: Al Capone, Roxy Hart, Baseball, Wrigley chewing gum. None of these things are particularly inspiring, but post visit I have come to the conclusion that Chicago is by far the most interesting city I have visited in the US.

The people are friendly, relaxed; the architecture is layered: intricate yet brash, old and new side by side often merging together. This city that is dominated by water – whether that’s the river that flows backwards or the sea that is really a lake, has taken on the personality of a seaboard city: renewing, outward looking; vibrating with life.

The lust for life of this city is evident in its devotion to eating out and drinking. Chicagoans for sure know how to have a good time. At first I was baffled by the vast number of coffee shops everywhere, but by the second night of drinking hard liquor like it was prohibition once again, I understood the need for coffee.

Back to the drinking habits of the grown-up and reckless. Basically I had great craic compiling this guide for you. Chicago is a big city of 3 million people, so my ‘hoods were basically Downtown, Near North, Old Town and a special trip out to Uptown/Andersonville.

So get your game face on, Chicago is all about craft brewing and craft cocktails. Not for the faint hearted, here is my guide to our favourite bars in Chicago – from dive bars to champagne bars and everything in between.

Monk’s Pub

Monks Pub Chicago

Monk’s pub is as old as I am, but it looks like it was placed here from Tudor England – all wattle and daub and latticed with oak beams. But pass through the doors and you walk into a bonafide Beer Halle that wouldn’t be amiss in the foothills of the Bavarian mountains. A craft beer and cider menu that will take you at least 15 minutes to sift through is a sign of good things to come. There are drinks on the menu here that you would simply never find in Ireland. My two tipples of choice? Clover Club – an American Wild Ale with Gin Botanicals and Raspberries coming in at 6.2% from Hopewell Brewing Co in Chicago; swiftly followed by a Ginger Peach Cider at 6.9% Vanderbilt Mill cidery.

Jake Melnick’s Corner Tap

Jake Melnicks Corner Tap

Not your average sports bar, the selection of craft beers here is great – not as huge as in some places, but that’s because the vast majority of their beers are on cask with seasonal offerings and showcasing of beers that are “tapping now” keeping things interesting. Take a seat at the bar and befriend your bar server to get the best out of the experience. Great selection of Chicago craft gins on offer as well as seasonal craft cocktails on tap – but don’t let that fool you into thinking they’re no good! Tapped cocktails pack a punch, are hand crafted to in-house original recipes and using the best of small batch craft spirit makers.


Rockbottom is a chain of brew bars in Chicago, but each brew their beers on site and have a dedicated brew master. All this means is that it doesn’t have the feel of a chain which is good. Beer flights are available here and are served up on beer mats that double as tasting notes. They have a five beer flight ranging from an entry level Pils style through to dark stout via a hoppy IPA. My personal favourite was the Malty Red, delivering on nutty, caramel flavours with a mellow yet light maltiness – perfect for a summer tipple. Growlers behind the bar enables dedicated punters to head for home with a naggin of their favourite beer.

Pippins Tavern

Pippins Tavern

So, if you’re looking for salubrious surroundings, don’t come here. But if you’re looking for a spot to have a beer at the bar in a small, friendly neighbourhood style pub in the middle of Downtown then Pippins Tavern is for you. It’s been here for over 40 years and is a hopping spot – the first time we tried to get in, we physically couldn’t so we came back another day! The bar is in centre of it all, and the best seats in the house are to be found there as you chat away to the friendly bar staff. An added bonus is that it sits right next door to Downtown Dogs so you can order in a quintessential Chicago Dawg to chow down on while sipping on a pint of Guinness – which is good here.


Fado Irish Pub

A massive Irish pub that is actually an Irish pub and not a gimmick of one! Owned and operated by a group of Irish entrepreneurs, their aim is bring the best of the Irish Pub to Chicago and mix it up for the 21st Century. There’s Guinness and plenty of Irish whisky to choose from, U2 and Drop Kick Murphy on the stereo, and the food is a mix of Irish traditional and Chicago classics all scratch made in their kitchen with carefully chosen ingredients – you can even get black and white pudding here for your Full Irish Breakfast! Like a pub in Temple Bar, the drinks are also extortionate – for that added “feels like home” touch. However, despite all of that, this was a really fun spot with great service – party central and a great place put away that few too many.

Green Mill Cocktail Lounge

Green Mill Cocktail

Way out of Downtown, the strip where you can find Green Mill feels like it is frozen in time. This was Al Capone’s old stomping ground, and the Green Mill Jazz Club is where he used to hang out with his henchmen. Stepping inside, it’s clear the décor hasn’t changed, and in the fading light of early evening, the bar is busy and Andy Brown is playing sultry acoustic jazz guitar behind the bar. I try something called Jeppsons Malort because, apparently, “you can’t visit Chicago and not drink Malort.” Thankfully, this baptism of fire only has to be attempted once. As we’re outside of Downtown, two things become abundantly clear – the measures are bigger (much bigger) and are half the price. Sweet. You simply have to come here.



Styled on a Belgian Moules and Frites hophouse, Hopleaf is a big, beautiful, busy maze of double height rustic brickness. The beer menu is really very good. Pretty much anything you choose will go well with your Moules and Frites, but if you really want to stay true to form then there is a great selection of Belgians to sup. Harking back to what was said previous, I like what the American’s do with Cider – so I went with Zombie Killer: a Cherry Cyser (mead and cider together – very yum), made with Michigan tart cherry juice, apple cider and star thistle honey. Served in a Goblet to disguise its 6% punch with ice – absolutely delicious!


Vincent Chicago

Chic Italian restaurant and cocktail bar tucked down a little side street – 100% neighbourhood spot, tourist free – except for us, so I guess now the secrets out! The cocktail menu is a well thought through revamp of the classics, marguerita, whisky sour, Sazerac, served in elegant glassware; even the garnishes were classy and understated! Vincent’s is thankfully gimmick free – modern and classy with hints of cheekiness: black painted walls, crystal chandeliers and giant gilded mirrors. Definitely a place worth getting dressed up for and making a night of it.

Broken Shaker at The Freehand


Hands down, this was top of my list of bars in Chicago Chicago. Technically, it’s a hotel bar. There are many things I like about this place, but most of all I love the fact that it has kept the 70’s vibe from the hotel’s days as The Tokyo, but refined for the present day taste of the modern-retro vibe. Every very infusion, tincture and bitter is handmade by the mixo-team making every single one of their cocktails truly unique. My first selection was ‘Insider Trading’: Dewer’s Scotch, Beefeater Gin and St Germain shaken with an Earl Grey Reduction, Sage, Citrus and topped with Soda – it tasted as complex as it sounds, the heady herbal notes definitely helping to counter the heavy alcohol, with a pallet refreshing citrus finish.

Pops for Champagne

Pops for Champagne

If your penchant is for something altogether more sparkly, then Pops is for you. Here, there’s no such thing as a simple choice between Champagne, Cava and Prosecco. Today, you have to choose between 250 different types of Sparking Wine from all over the world, or maybe one of their sparkling wine cocktails is more your thing? Repeatedly selected as the best Champagne Bar in the entire USA not just for their selection but also for their commitment to seeking out the very best grower-producers, an ethos that lends itself to stocking only the best quality sparkling wines.

The Purple Pig

The Purple Pig

Twice we attempted to get a table here, twice we failed. It seems the “Cheese, Swine and Wine” on offer here is a crowd-drawer and crowd-pleaser well worth the wait (one hour minimum mid-week in low-season!). The Purple Pig has received numerous awards including the coveted James Beard and is a four-time Michelin Bib-Gourmand recipient. At a guess, the crowd is a 50/50 split of tourists and locals (given its location at the top of Michigan Avenue) and although usually a tightly packed restaurant would turn me off, on this occasion I would admit that this is the one that got away. So, word of advice, book a table well in advance to avoid crushing disappointment – especially if visiting in high-season.


Kate Ryan Flavour.ieKate Ryan is a food writer, blogger and founder of a website that is dedicated to promoting West Cork Food through writing, events and tours. Kate writes regularly for The Opinion Magazine and The Southern Star newspaper and has been featured in the Irish Examiner and Irish Times. Her blog is recipe driven showcasing the best of West Cork produce and encouraging everyday cooking with it at home as well as the best places to eat in the region. Kate hosts a very popular social dining “Supper Club” as well as organising a variety of food-related events getting people to enjoy great local food together. In the summer season, Kate also runs the only guided Walking Food Tour of Clonakilty which takes place every Friday June to August and is accredited by Fáilte Ireland for the Wild Atlantic Way. Kate is also a judge with Blas na hEireann and the Irish Quality Food Awards.

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