An intimate and immersive experience at Rose Mary's Chef's Counter for four guests, offering a front-row seat to the open kitchen as Chef Joe Flamm and Chef de Cuisine Brian Motyka's team create an ever-evolving tasting menu inspired by the finest micro-seasonal ingredients from the Midwest.

Rose Mary has earned national recognition for its distinctive Croatian-Italian cuisine and wine program, including multiple Wine Spectator Awards of Excellence and two appearances on OpenTable's Top 100 Restaurants in America. Chef-owner Joe Flamm is a James Beard Award nominee and winner of Top Chef Season 15, while Rose Mary's leadership team was named a 2026 James Beard Award semifinalist for Outstanding Restaurateur.

Value: $1,000

Woodshed Wine Company: VIP Tour & Tasting Experience + 6 Bottles of Library Pinot Noir

Get ready for a one-of-a-kind adventure in Dundee, Oregon with this exclusive experience from Woodshed Wine Company. The journey begins with a VIP off-road Jeep tour led by owner and winemaker Anthony Van Nice, who will personally guide you through rugged vineyard terrain and share the stories behind the land, the vines and the wines that define Woodshed's bold spirit. After the tour, settle in for an intimate and rare Old Vine Pinot Noir library tasting hosted by Anthony. Sip through a curated selection of limited, aged vintages that showcase the complexity and character only time and old vines can offer. This tasting offers a deep dive into the craft of winemaking and the evolution of Pinot Noir, all in the company of one of Oregon's most passionate vintners. In addition to the tour and tasting, we will mail you a library selection of Woodshed's Estate and Old Vine Pinot Noirs from our first vintage in 2018 to 2021.

Beaux Freres Private Estate Experience + Rare 3L Pinot Noir

Enjoy a private Panoramic Tour & Tasting at Beaux Freres for up to six guests. Explore the vineyards and winery in the Ribbon Ridge AVA, learn about the farming and winemaking behind the estate, and conclude your visit with a curated tasting of current and limited-production wines.

The package also includes a rare 3-liter bottle of the 2018 Beaux Freres Vineyard Pinot Noir - the wine named #9 in the world by Wine Spectator in its 2020 Top 100. An exceptional opportunity to experience Beaux Freres firsthand and take home a collectible large-format bottle from one of the estate's most celebrated vintages.

A Home Base in the Heart of Wine Country

Rest and recharge between tastings with a stay at the Tributary Hotel & Spa, a boutique retreat in downtown McMinnville - the gateway to Willamette Valley wine touring. With refined rooms, a full-service spa, and easy access to the region's top wineries, it's the perfect place to unwind after a day exploring vineyard terrain and sipping library Pinot Noir.

Getting There in Style

To help you make the trip out west, this package includes 100,000 American Airlines miles - enough to cover flights for you and a guest to Portland, gateway to the Willamette Valley - so all that's left to plan is which vineyard to visit first.

Details:

• Tour and private tasting at Beaux Freres
• Tour and private tasting at Woodshed
• Stay at Tributary Hotel + Spa
• 100k American Airlines miles

Value: $6,350

Turn your next gathering into an unforgettable evening with this luxurious, chef-curated in-home dining experience for 10 guests. The acclaimed team at The Entertaining Company will transform your home into a private fine dining venue, preparing and serving an exquisite, fully catered dinner that blends artful presentation with bold, trend-setting flavors. Known for their creativity and flair, The Entertaining Company uses artisan ingredients to craft a menu that is as visually stunning as it is delicious.

The Wine

Complementing your evening is a pair of exceptional Bordeaux. The 2002 Chateau Lafite Rothschild earned 95 points from Wine Spectator, praised for its crushed berries, currants, and spices with tobacco notes, and described as a "racy yet elegant Lafite" with velvety tannins and a long, fruit-driven finish. The 1995 Lynch Bages, rated 94 points, is a wine that Wine Spectator notes, "continues to improve with age, showing ripe plum and prune notes alongside hints of vanilla and mineral in a full, chewy structure."

Details

• In-home dining experience for 10
• One (1) bottle 2002 Chateau Lafite Rothschild
• One (1) bottle 1995 Lynch Bages

Value: $6,000

Get ready for a party like no other - irreverent, indulgent, and unmistakably Chicago. You and up to 100 guests will take over the entire back patio of The Wieners Circle, the city's most iconic late-night hot dog stand, for a private event that's equal parts gourmet and goofy.

This one-of-a-kind celebration includes:

• Wine and wieners, Burgundy and burgers, Champagne and cheese fries - a wildly fun mash-up of high-end wines paired with classic Chicago comfort food. Expect a playful, elevated take on your favorite guilty pleasures, all served with a wink and a smile.
• Curated selection of wines - includes two mixed cases featuring cabs, burgundy and treats from Bordeaux.
• Custom message on The Wieners Circle marquee - your party kicks off with your own cheeky welcome message featured on Chicago's most notorious and beloved signboard, setting the tone for an unforgettable night.

With an open-air vibe, legendary staff, and a lineup of food and drink that bridges the gap between street food and sommelier-approved sips, this is the ultimate way to celebrate a milestone, host a client event, or just throw a blowout your friends will talk about for years.

Mutually agreed upon date and time.

Value: $8,000

This exclusive package includes three nights for up to eight guests across four rooms, offering the perfect opportunity to gather family or friends for an extraordinary Irish getaway. Guests will enjoy Ballyfin's renowned hospitality while exploring the estate and its many activities, from leisurely walks and outdoor pursuits to time spent simply taking in the beauty and tranquility of the grounds.

There's nothing else in Ireland quite like Ballyfin. This spectacularly well-preserved Regency house sits on no fewer than 614 acres of parklands and woodlands, a mere hour outside of Dublin. And if the exterior is a pitch-perfect restoration, worthy of a 19th-century period film, the interiors are a contemporary-classic evolution of the house's original style, an opulent fantasy to rival any country-house hotel you could name.

The main house contains a mere 20 rooms and suites, all of which combine lavish antique style and modern luxury-hotel comforts. Meanwhile the Gardeners Cottage has been made into a self-sufficient residence for two, a two-story house complete with its own kitchen and dining room, as well as a hot tub on its private terrace.

At the center of daily life lies Ballyfin's eight-acre walled garden, supplying the kitchen with seasonal fruit, vegetables, and herbs. Executive Chef Richard Picard-Edwards shapes menus in close collaboration with the garden team; in early 2025, the kitchen was awarded a Michelin star. Dinner is served in the candlelit State Dining Room, with lunch in the Turner Conservatory, accessed via a hidden door behind a bookcase in the Library. Private dining can be arranged in a variety of intimate settings across the house and estate, while guests may also explore the wine cellar, enjoy Irish whiskey tastings, or retreat to the Picnic House for a secluded lunch.

The Wellness Area provides a serene space to unwind, with a naturally lit swimming pool, vitality pool, sauna, gym, and treatment rooms. Guests can enjoy a variety of estate activities including falconry, clay pigeon shooting, archery, horse riding, fishing, guided walks or horse & carriage tours.

Ballyfin is a proud member of Relais & Chateaux, recipient of 1 Michelin Star and 3 Michelin Keys.

Details:

• Wine tasting, whiskey tasting and one (1) activity per person included.
• 400,000 American Airlines miles

Value: $38,500

A Better Chicago identifies and invests in the city's most promising nonprofits led by community leaders.

Together, we're helping thousands of young people access tutoring, mentorship, college support, and career opportunities.

Your gift supports a portfolio of organizations creating life-changing opportunities for Chicago youth. A Better Chicago is a 501(c)(3) nonprofit, and your donation is tax-deductible as allowed by law.

Join us for a game of Heads or Tails at Grape + Grain!

Pre-order your chances now, and we'll have a blinky ring (or 3!) waiting for you at the event to mark you as a player.

The prize package includes 4 tickets to a Bulls game, with other prizes being added to the package in the coming days - so it's going to be special, and you won't want to miss your shot at it.

How Heads or Tails Works

Each player picks heads or tails before the coin is flipped. Guess right, and you're still in - guess wrong, and you're out. We'll keep flipping round after round until only one player remains, and that player takes home the prize.

You can pre-order up to 3 chances, so if you're eliminated early, you may still have another shot in play.

Limit of 3 chances per attendee.

Didn't win the live auction lot you had your eye on? Here's your second chance. Join us for the Paddle Drop at Grape + Grain - a great way to get involved even if you're not walking away with an auction win, or if you simply want another shot at a great prize while supporting the incredible work A Better Chicago does for young people across Chicago.

The prize will be announced closer to the event - but it's going to be special, so you won't want to miss your shot at it.

This is just a preview - the Paddle Drop will only be available the night of the event.