For arguably the most impressive views in town (with lofty prices to match), Trump Tower’s Terrace offers close up and personal views of the upper reaches of a few of Chicago’s most famous landmarks—Tribune Tower and the Wrigley Building. Views of the river, lake and fireworks (on Wednesdays and Saturdays) aren’t bad either.
Closer to the ground, it’s tough to beat Piccolo Sogno which has one of the most verdant, idyllic dining decks anywhere. Barely out of the Loop, this fine Italian dining restaurant is hardly your typical red sauce joint. The other night I took a friend from New York City here and she was so smitten with its pastoral charms that her allegiance to her native city seemed to falter.
For a more casual Italian option, grab a table at Enoteca Roma which serves Roman style pizza, pastas and other standbys featured at traditional Eternal City eateries. Division Street, with its ultra-wide sidewalks and effervescent pedestrian scene, is an ideal setting for this casual spot which offers both an expansive café and a private courtyard in back.
For scenesters, Sushi Samba Rio’s rooftop aerie offers music, crowds, music, views and tasty, unconventional food that merges Japanese cuisine and sushi with the culinary traditions of South America.
Not to be outdone, newbie Epic boasts the largest rooftop spot in the city—and perhaps even the world. Smartly designed, cavernous rooms offer agreeable indoor spaces in which to spend some time, but the rooftop which seems as large as a football field is where the action is during the summer months.
Finally, the concrete, cacophonous sidewalk café scene at Matchbox offers perfection in a cocktail glass and plenty of urban grit. Handcrafted cocktails were a mainstay here long before the term was coined, so look for expertly mixed classics and no-nonsense bartenders.
Okay, so these are some of my favorites, what are yours?