| Hubbard Inn | | Brunch at Hubbard Inn | | Restaurant serves upscale takes on brunch favorites, such as pork belly benedict and lobster omelets | | | | | | |
| Gejas Cafe | | Romantic Fondue Dining at Geja's | | 200 fine wines complement sweet and savory fondues at this eatery voted #1 of 20 of the country’s most romantic restaurants by USA Today | | | | | | |
| Leona's Pizzeria | | Pizza, Pastas, and Wings | | Savor cheesy pizzas, wine, pies, wings, and pastas such as spinach ravioli in a family-friendly dining room | | | | | | |
| 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. | | | | | | |
| 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 | | | | | | |
| Cold Stone Creamery | | Ice Cream | | Mix-ins blend with fresh-churned ice cream to create unique flavor combinations | | | | | | |
| 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 | | | | | | |
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| 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 | | | | | | |
| Two | | Dinner for Two with Wine at Two | | Michelin Bib Gourmand restaurant’s ever-changing midwestern plates include butcher-themed dishes alongside fresh seafood & house-made pasta | | | | | | |
| Venezuelan Bowl Grill | | Venezuelan Food | | Lincoln Park eatery decorated in the colors of Venezuela’s flag serves authentic fare, including arepas and rice bowls | | | | | | |
| Al's Char-House | | Steakhouse Cuisine | | Diners feast upon juicy steaks and seafood inside a wild west-themed restaurant adorned with old photographs and cowboy memorabilia | | | | | | |
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