Chicago has a lot to offer – architectural gems, a great comedy scene and a predilection for pies. With so much to do, see and eat, we’re taking a very literal approach to drinking it all in with our edit of seven of Chicago’s best spots to have a tipple during the day. Hey, you’ve got to start somewhere.

Lost Lake

A tropical cocktail bar in Chicago’s Logan Square neighbourhood might seem out of place, but Lost Lake knows have to convert even the greatest of sceptics. Well versed in all things rum, it has a 30s-Hollywood-meets-tiki-bar aesthetic. Still need convincing? Indulge in a bar-within-a-bar experience at Lost Lake’s Stranger in Paradise.


Pull up a stool at this gin-focused cocktail bar which caters to a diverse clientele. Whether enjoying a beer and brunch on the sun-drenched patio or a Baileys and freshly baked cookies at midnight, you’ll most likely find us at Scofflaw anywhere from sunrise to sunset.


In the bar-populated Pilsen neighbourhood, Simone’s stands out from the crowd. The bartop is built from a former bowling alley lane and the booths have been fashioned from old pinball machines. Regulars are known to make a beeline for the DJ booth at the far end of the bar, which comes complete with a cage for holding groupies.


Cindy’s sits at the top of the Chicago Athletic Association building, but the open-air terrace is the antithesis of a tired men’s club – it’s far more dynamic. Order some classic comfort food and pair with its selection of biodynamic wines, or rally your friends and avail of its “apothecary services” cocktails (which serve 10).

Longman and Eagle

Day drinkers can take comfort in the fact the Longman and Eagle comes with sleeping options. With over 400 whiskeys available and over three dozen on offer daily (for only $3 a shot), it’s often the case that booking a room is less of a nice add on and more of a vital next step.

C.C. Ferns

The morning after the night before is rarely helped by coffee. At C.C. Ferns order a boozy steamer and treat that hangover with the hair of the dog; it’s our pre-noon answer to the espresso martini.

Soho House Chicago

As in most cities you’ll find the creative crowd (with an affinity for rooftops) at local Soho House. With the number of people growing throughout the day, your best chance of nabbing a table or the holy grail (read: a couple of sun loungers) is to arrive early and stay until dusk. The day is cheaper than you might expect if you order from its 3 6 9 menu on the fifth floor, which offers a mix of smaller bites. Cocktails here are dangerously drinkable – we’ll have the picante de la casa times three please.

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City Guides

You know how you have that one incredible friend who knows their city inside out? That’s us. We take the world’s most dynamic destinations, hand-pick the best bits and give them to you in one place. This is the kind of guide that you don’t need to run by a local – it was written by one. Eat your heart out, shop until you drop, drink like a fish, dance your socks off, sleep – then repeat.


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