Much has been said about expectations, and how they can rise to the clouds and plummet to the soil, in reverse levels, and repeatedly. As a wanderluster, I have learned to tame my expectations based on what I know of places, without letting too many preconceived notions fog my thoughts. For the moment of surprise, when an expectation is met, surpassed, or falls flat on its face, is priceless.

Which is why, politics aside, I didn’t mind perching on the rooftop bar Terrace 16 of the Trump Chicago, who’s Michelin Star Sixteen I had dined lusciously at before, too. Which only started a two part night up in the clouds. While we skipped the food, we opted for the ambiance of the idyllic terrace with views of the Chicago River and architectural landmarks, which were fun to spot over mixologist recommended cocktails.

Between us we shared two favorites of potent mixology: the absinthe frappé with grande absinthe, mint, citrus and an ice cube infused with cotton candy! The tart flavors were subtly strong, cooled by the mint on a hot night, with the best part being the sweet ice cube, which exuded flavor as it melted. The neon green table lamps ensured it’s color was akin to a wicked witch of the west (touché) while it lit into an iconic gold against the city’s backdrop. By comparison, the Kentucky spring with buffalo trace, ginger, mint and peach tea was a twist on a spirit forward boozy drink, with undertones of fruity flavor that made it simultaneously gender neutral – if such a concept existed for drinks!

On feeling a fetish, we waltzed outside the hotel for a riverwalk stroll, only to stumble into a neon lit (obsessed!) Berkshire Room, helmed as one of the finest cocktail bars in this culinary city. A craft cocktail lounge, with drinks created Christian Hetter and Benjamin Schiller, this was a perfect late night date spot offering bliss in the dim lit, archways and kiss worthy ambiance. What with benches under arches and dim lit cellars holding prestigious liquors, it was akin to a fantasy.

Especially when our drinks arrived, starting with salted caramel chocolate cookies with a side of bourbon milk! The whiskey and milk combination seemed to be thoroughly trending, and paired with my all time favorite cookie meal, made for an indulgent snack that was simultaneously childlike and naughty. Paired with a beet chocolate cream cake, which tasted equal parts beet as it did dark chocolate, rendering it un-saccharine, I was in blissful heaven.

By comparison, the perfect pear vodka drink, arriving in a curious vial where even the stem was filled with liquor, was more adult and less childish, much to our mood’s dismay but tastebuds’ delight. Vodka, riesling and pear cordial and chartreuse combined to make a smooth, boozy and flavorful drink, which overshadowed every element of desserty froth that may have caked our lips and tongues.

They say you sip to shut your body down. But with a wildly creative experience that I repeated repeatedly, it was time to paint the city golden.