The Gold Coast may be frou frou, so while you're there, indulge in some frou frou food and wine.
Le Colonial is one of the best restaurants in Chicago. Super fresh, tangy, spicy, sweet, wonderful, awesome. That's just the food. The atmosphere is lovely, class, first-rate. Love. This. Place.
An oldie but a goodie. Forget the trendy, just-opened spots every once in a while and indulge in a 12-oz. filet, a double decker martini and a taste of old school Chicago.
Tavern on Rush is good food, good service, but the best darn people watching ever. Make sure to sit outside and watch the people coming and going, walk of shaming (at pm) or heading to the Viagra Triangle.
Perched in the Park Hyatt Hotel on the 7th floor w breathtaking views of Michigan Ave, it's hard not to love this fancypants "casual dining" resto even if a spicy tuna roll is $21.
If you'd like to indulge in a $7 latte, I think I'd recommend that it's worth it here.
Forget stodgy and stuffy, the Four Seasons is officially a hotspot for the trendsetting crowd. Chef Kevin Hickey is the coolest Four Seasons chef in - uh - the whole world.
Hugo's is one of my classic favorites. With a name like "Frog Bar & Fish House," it's almost a mandate to order their fresh fish, but they do in fact share a kitchen with the famous Gibson's steak house for landlubbers out there.
TR Napa is a little bit overpriced and their is a little under educated. But it's centrally located with a great wine list. You can't have it all...