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).

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.