| Superdawg Drive-In | | Superdawg Drive-In | | Since 1948, two drive-ins serve Superdawgs, Whoopercheesies, Supershakes, and crinkle-cut fries beneath rooftop hot-dog statues | | | | | | |
| 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 | | | | | | |
| Cold Stone Creamery | | Ice Cream | | Mix-ins blend with fresh-churned ice cream to create unique flavor combinations | | | | | | |
| 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. | | | | | | |
| Trenchermen | | Dinner at Trenchermen | | “Bon Appetit” and “Food & Wine” have praised this Wicker Park restaurant’s playful take on dishes like roast quail and potato gnocchi | | | | | | |
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| Yogurtland | | Yogurtland | | Yogurt made from antibiotic- and hormone-free milk with such ingredients as thousands of pounds of pistachios and one ton of tangerines | | | | | | |
| BIG & little's Restaurant | | BIG & little's Restaurant | | Hell's Kitchen chef creates an internationally inspired menu that showcases crab po’ boys, ahi tacos, and beer-battered cheeseburgers | | | | | | |
| The Southern | | Southern Dinner or Brunch | | Wicker Park spot puts an upscale twist on Dixie classics such as fried green tomatoes, Nashville hot wings, and shrimp and grits | | | | | | |
| River Roast Social House | | Roasted Meats and Vegetables | | Roast dinners and shared dining with table-side carved whole-roasted chicken, roast beef, pork, and fish served with savory side dishes | | | | | | |
| Vie Restaurant | | Tasting Menu at Vie Restaurant | | Michelin-starred chef Paul Virant serves course after course of seasonal cuisine lauded in the Chicago Tribune and Gayot | | | | | | |
| 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 | | | | | | |
| The Bedford | | The Bedford – Cocktails & Dinner | | Shareable twists on classic American cuisine served in the glittering interior of a repurposed 1920s bank vault | | | | | | |
| 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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