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1. Raffaello Hotel 201 East Delaware Place, Chicago, IL 60611 (Gold Coast)

Recently renovated and centrally-located on Michigan Ave, Raffaello serves up 24-hour room service, full concierge services, and a next-lever rooftop speakeasy they call Drumbar.

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2. Talbott Hotel 20 E. Delaware Place, Chicago, IL 60611 (Gold Coast)

Originally built in 1927, Talbott's a boutique Gold Coast relic on Delaware Place that juxtaposes antiquated decor with modern technology.

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3. PUBLIC Chicago 1301 North State Parkway, Chicago, IL 60610 (Gold Coast)

With 285 over-sized rooms in the heart of Gold Coast, Public offers everything from complimentary breakfast in bed, to grub from insanely famous chef Jean-Georges Vongerichten.

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4. The Drake 140 East Walton Place, Chicago, IL 60611 (Gold Coast)

The Drake has endeavored to be one of the first urban resorts in the nation for almost a century... so please don't refer to it as the Drizzy.

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5. theWit Hotel 201 N. State Street, Chicago, IL 60601 (Loop)

For an energetic hotel situated amongst a lengthy lineup of historic Chicago landmarks, check out theWit.

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6. Penthouse Duplex North State Street, Chicago, IL 60611 (River North)

A two-story penthouse with unobstructed city views located smack-dab on Magnificent Mile.

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7. Longman & Eagle 2657 N Kedzie Ave, Chicago, IL 60647 (Logan Square)

Longman & Eagle, the Michelin-starred gastropub in Logan Square, has an exclusive whiskey selection (clocking in at over 400 labels), a craft cocktail menu, and an extensive beer list all fit for the most pretentious of drinkers, in the least pretentious of atmospheres. Longman takes a flavor-forward, honest approach to eating and drinking, and because it doesn’t accept reservations, there is always a wait for brunch, happy hour, and dinner alike. (And it is always worth it.) While whiskey may be king, the regional American fare has just as much to offer, hence the Michelin star. The menu changes often, but expect anything from beef tallow beignets and veal brains to wild boar sloppy joes, chicken and waffles, and a burger that, if you know what's good for you, you will order.