1. Cocktails at The Aviary
To set the mood, start things off right at a memorable cocktail spot. Grant Achatz, world-renowned chef and restauranteur, is the driving force behind The Aviary, a unique lounge featuring artisan cocktails and eighteen different types of ice (yes, really), all held in custom-designed glassware (yes, really) that will give you plenty to talk about. From the man that brought us Alinea, you can expect drinks that are nothing short of amazing.
The Aviary, 955 West Fulton Market (at Morgan Street).
2. Dinner at Girl And The Goat
The Girl and the Goat is popular for more than just owner Stephanie Izzard's Top Chef win. This first-class Chicago restaurant has thrilled critics and Chicagoans alike with locally sourced ingredients and compelling combinations. It's not necessarily recommended for herbivores, but adventurous eaters will get excited about goat empanadas, ham frites, and chicken noodle soup bread. Eating off each other's forks is encouraged... who wouldn't want to try as many plates as possible? Girl and the Goat, 809 West Randolph Street (at Halsted Street); 312) 492-6262.
3. Dessert and Aperitifs At Maude's Liquor Bar
Aperitifs and Desserts are essential to keep date night conversation going, and what better romantic locale to head to than Maude's Liquor Bar? The mood lighting, shimmering crystal glasses, and dark wood make for perfect ambiance. The crème brûlée is the size of a soccer ball and is the best we've ever tried. A boozy St. Germain Fizz or Smokey Violet Smash will leave you feeling light-headed and relaxed for what will (hopefully) be a very sweet end to your evening.
Maude's Liquor Bar, 840 West Randolph Street (at Green Street); 312-243-9712.