Z Bar

Perched 6 floors above Michigan Avenue, Z Bar delivers the kind of rooftop experience that makes you forget you're in the middle of downtown Chicago. The panoramic city views compete for attention with the meticulously crafted cocktails—each one arriving like a tiny work of art that you almost feel guilty drinking. Almost.

The crowd skews touristy, but the sophisticated atmosphere keeps things from feeling like a visitor trap. While the beer selection won't impress your craft-loving friends, the cocktail program more than compensates with inventive concoctions that justify the eye-watering prices.

The full food menu offers elegant bites perfect for sharing, though you might not want to after tasting them. When the live music kicks in as the sun sets over the skyline, you'll understand why reservations are essential. Yes, it's splurgy, but some views—and some perfectly balanced negronis—are worth the investment. Just don't expect to find parking easily, or your bank account to thank you later.