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| 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 | | | | | | |
| Yogurtland | | Yogurtland | | Yogurt made from antibiotic- and hormone-free milk with such ingredients as thousands of pounds of pistachios and one ton of tangerines | | | | | | |
| 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 | | | | | | |
| 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. | | | | | | |
| 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 | | | | | | |
| Hala Kahiki | | Tiki-Bar Drinks and Snacks | | Tropical cocktails named for Pelé and coral reefs poured in Polynesian-themed bar opened in 1963 | | | | | | |
| Hubbard Inn | | Brunch at Hubbard Inn | | Restaurant serves upscale takes on brunch favorites, such as pork belly benedict and lobster omelets | | | | | | |
| The Vino Cellar | | Wine and Cheese for Two or Four | | Three white or red wine samples accompanied by a cheese plate with cheddar, havarti and gouda | | | | | | |
| 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 | | | | | | |
| 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 | | | | | | |
| House of Hookah | | Hookah and Non-Alcoholic Drinks | | This late-night BYOB hookah lounge features 70+ hookah flavors, plus a wide variety of hookah accessories for purchase | | | | | | |
| The Bedford | | The Bedford – Cocktails & Dinner | | Shareable twists on classic American cuisine served in the glittering interior of a repurposed 1920s bank vault | | | | | | |
| Kingston Mines | | Blues Concert for Two | | Legendary blues club stages performances by equally legendary blues musicians seven nights a week | | | | | | |
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