| Fig & Olive - Chicago | | Mediterranean Lunch or Dinner | | Cuisine inspired by the Mediterranean regions of France, Italy, and Spain infuses olive oil into sweet and savory dishes | | | | | | |
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| Kingston Mines | | Blues Concert for Two | | Legendary blues club stages performances by equally legendary blues musicians seven nights a week | | | | | | |
| Cold Stone Creamery | | Ice Cream | | Mix-ins blend with fresh-churned ice cream to create unique flavor combinations | | | | | | |
| Lao Sze Chuan | | Seven-Course Duck Dinner | | Restaurant overlooking the Magnificent Mile offers a seven-course dinner featuring its signature dish of peking duck with Sichuan cuisine | | | | | | |
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| Elizabeth | | Inventive Tasting Menu | | A Michelin-starred 7- to 9-course tasting menu full of Midwestern bounty. Elizabeth draws inspiration from local farms, gardens, and nature. | | | | | | |
| Pizzeria UNO | | Deep Dish Pizza-Cooking Class | | Students learn how to craft their own deep dish pizza at a restaurant that’s been making them since 1943 | | | | | | |
| The Murder Mystery Co. | | Murder-Mystery Dinner | | Interactive murder mystery dinner starring professional actors testing guests' sleuthing skills throughout a three course meal | | | | | | |
| Emporium Arcade Bar | | Emporium Arcade Bar | | Visitors juggle drinks and joysticks at the arcade bar’s two locations, where vintage video games and pinball tables abound | | | | | | |
| Wisconsin Great Northern Railroad | | Dinner-Train Bed and Breakfast | | Tasty 5-course meals unfold in a vintage 1950s dining car as the train rides through the woods; a 1950s sleeper provides cozy accommodations | | | | | | |
| Oceanique | | French Seafood Dinner | | Seasonal fish, organic local produce, sorbet, and pastry praised by Time Out Chicago and the Chicago Reader | | | | | | |
| La Gondola Italian Restaurant | | Italian Dinner | | Hand-tossed dough yields deep-dish pizza, and a signature breading cloaks calamari in an awarded eatery rated by Zagat 20 years in row | | | | | | |
| Karyn's cooked vegan | | Cooked and Raw Cuisine | | Raw cooked vegan menu includes gluten-free alfalfa-sprout enchiladas, zucchini-noodle spaghetti and vegan meatballs, and kale salad | | | | | | |
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