| Chicago Hauntings Ghost Tour | | Ghost Bus Tour | | Paranormal experts narrate a bus tour; specialty tours explore haunted sites inspired by the city’s gothic past or the notorious H.H. Holmes | | | | | | |
| 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 Bedford | | The Bedford – Cocktails & Dinner | | Shareable twists on classic American cuisine served in the glittering interior of a repurposed 1920s bank vault | | | | | | |
| 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. | | | | | | |
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| Village of Bensenville | | Movie and Snacks for Two or Four | | Guests grab buckets of popcorn and large sodas before heading into intimate twin theaters to view recent releases | | | | | | |
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| Cannonball Productions | | Michigan Winery Tour | | Sample wines from Southwest Michigan wineries including Lemon Creek, St. Julian, and Round Barn on this day tour; includes lunch | | | | | | |
| 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 | | | | | | |
| 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 | | | | | | |
| Kingston Mines | | Blues Concert for Two | | Legendary blues club stages performances by equally legendary blues musicians seven nights a week | | | | | | |
| Best Tours | | Wine and Cheese Tour of Chicago | | Stroll along the Magnificent Mile and through the Gold Coast as you sample 12 bites of cheese paired with sips of wine | | | | | | |
| Color Cocktail Gallery | | BYOB Painting Classes | | Instructors with MFAs from the School of the Art Institute of Chicago lead laid-back BYOB painting classes at their studio space in Pilsen | | | | | | |
| 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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