Whiskey Sky

For Lake Michigan views, there's the Signature Lounge and there's Whiskey Sky. Perched atop the W Hotel on Lake Shore Drive, Whiskey is where the under-40 crowd and the more sophisticated tourists go. Its shiny metallic bar and mirror-covered ceiling straddle the line between '80s chic and Miami cheese. The sunset scenes will make your heart explode, but weekends here are less than inspiring, with predictable crowds. Wallet-emptying prices should be expected, so bring the plastic.