Cindy's Rooftop

Perched atop the Chicago Athletic Association Hotel, Cindy's offers that rare combination of jaw-dropping views and drinks that actually live up to the scenery. The glass-enclosed rooftop opens to a terrace where you can sip expertly crafted cocktails while Lake Michigan stretches endlessly before you.

The crowd skews touristy (expect selfie sticks), but even locals can't deny the magic of watching the sunset paint Millennium Park in golden hues while nursing one of their seasonal gin concoctions. Their cocktail program shines brightest—though the curated wine list and local craft beers hold their own.

Yes, you'll need reservations. Yes, it's pricier than your neighborhood haunt. And yes, you might wait for a prime outdoor spot even with a booking. But when the heaters kick on during cooler evenings and the city lights begin to twinkle, you'll understand why everyone's willing to jump through hoops for a table. Come for the views, stay for the surprisingly excellent food—the shared plates are worth the splurge.