The Terrace at TrumpNear North
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This terrace lounge on the sixteenth floor of the Trump Tower boasts one of the best alfresco views in the city. To get there, take the elevator to Sixteen on the sixteenth floor and turn right. Thanks to a boomerang-shaped bar facing the terrace's edge, you can take in an impressive eyeful of the Chicago River and Lake Michigan, not to mention Navy Pier's seasonal fireworks on Wednesday and Saturday evenings. The space was especially designed for alfresco relaxing of all kinds: There are L-shaped couches for girlfriend groups sharing a bottle of bubbly, bistro tables and an 18-seat communal table cozied up right near the railing. A brief food menu includes salads, ceviche, gourmet sliders and skewers, but don't mistake this spot for a restaurant -- the focus is on the imbibing, through and through. Pricey cocktails get their sparkle from the addition of sparkling wines; the big star here, though, is the "rosé is the new black" wine list pimping a huge list of pink picks from all over the world, including a dozen by the glass and 30-plus by the bottle.