Freehand Chicago

A sensation in Miami Beach – part artful cocktail bar, part cheap sleeps. Has new home in Chicago’s upscale River North. Private or shared rooms, unfussy style with quirky art touches. Cafe Integral for morning jolt. But Broken Shaker is scenester spot, with snarky cocktails like the Banana Rum Manhattan and Cocoa Puff Old Fashioned, and a side of “street food” bites.

Acme Hotel

Hip and cheeky boutique hotel, blend of de rigeur old timeyness and kitsch art touches. Rooms are simply styled, no fuss, but comfy. Berkshire Room does ace cocktails in spectacular space, looks plucked from David Lynch film. In house West Town Bakery is sweetsters mecca.

Virgin Hotels Chicago

Richard Branson invites you to bed. Debut Virgin hotel does “affordable chic” model akin to The Ace or The Public. There’s nothing so boring as a “room” to sleep in here. Rather, they’re called “Chambers”—where hallway, closet and loo are combined into a “Dressing Room”, and sliding doors create a “Sleeping Lounge.” The scene? From breakfast to cocktails, the soaring-ceilinged Commons Club will be Virgin’s socializing central. There’s also the kitschy Miss Ricky’s Diner and the by now rather obligatory Rooftop Bar, serving Izakaya style tapas. Get deflowered.

The Langham

In legendary Mies Van Der Rohe building. Shames nearby Trump with its unassailable exquisiteness. Residentially styled rooms have glorious river views, while public areas exude ethereal modernism. Tim Graham’s Travelle restaurant racks up accolades with champagne risotto and Alaskan halibut – whilst namesake (and also river view blessed) lounge shakes and stirs some of city’s best cocktails. Chuan Spa is also one of city’s best. Fabulous, in every possible way.

Shake Shack

Not that Chicago needed better burgers. But inevitable arrival of Danny Meyer’s unstoppable force immediately caused lines that stretched for blocks. Of course, the burgers are amazing, and you’ll have to wait and wait and wait.

Tippling Hall

A Mercadito joint. Nouveau beer hall, oddly in partnership with cocktail maestros The Tippling Bros. Unfussy furnishings, but vaguely industrial-meets-Southern-roadhouse feel. Usual comfort food suspects (chicken pot pie, quinoa salad) with a few twists like duck confit empanadas. But you’re here to drink, And there’s even a Spinal Tap tribute cocktail called Derek Smalls – though we’re not sure The Tap ever drank anything with cucumber and mint in it. Go with the Frozen Sloshees for maximum downscale effect.

Tunnel

Hidden club above John Barleycorn, inspired by subterranean London…of all things. Not as radical as it sounds – rather, essentially another over-designed club, with futuristic light installations, lots of headache inducing blues and reds, bottle service, as well as up-and-comer DJ talent. Sexy, in just the sort of way you’d imagine.

Ramen-San

Slotted into Paris Club, cool noodle spot with beer fixation. Buzzy atmosphere, great for knocking back a few Singapore Slings, Sake Bombs or Asahi cold drafts. Pork belly mantou buns, spicy chicken wings, and creatively conceived ramen (try the smoked brisket & burnt garlic) make dinner a bit of a party every time.

Oak + Char

Sort of fancy outdoorsy inspired cooking from chef Joseph Heppe. Menu ranges from surprising (saffron tail pepper carbonara, Tandoori octopus) to sturdy (beef tartare, double prime cheeseburger). Rustic interior flounced up by unique tufted hanging light fixtures, which look curiously like an alien invasion.