There’s nothing wrong with splurging on lobster or king crab and wanting to enjoy it in this institution’s formal dining room. We just prefer to get down and dirty in the adjacent oyster bar, where we slurp fresh oysters, crack open crab claws and dunk lobster tail in copious amounts of butter. Classic cocktails are well-executed, though we'll almost always opt for a well-chosen draft beer alongside seafood.
Sixteen transformed itself under former chef Thomas Lents—with creative themed tasting menus like Chicago History, more approachable service and two Michelin stars, the restaurant is solidly in the top tier of fine dining in Chicago. While the tasting menu is firmly in the "splurge" category (dinner for two with wine pairings is around $1,000), the patio offers an even better view of the Wrigley Building and Tribune Tower, as well as less expensive food.
Topolobampo is the most sophisticated and upscale of Rick Bayless's restaurants, and the one most frequented by President Obama and his family. As with all of Bayless's restaurants, the products used here are local and seasonal. So whether you're eating fresh oysters or ceviche or one of the beautiful moles, you know you're eating the best the season has to offer. An ever-changing menu means it's hard to predict exactly what will be offered day to day—but because Bayless is involved, it never really feels like a gamble.