Enjoy a remarkable private evening of insight and conversation with James A. Robinson, HPDS parent, renowned economist, and 2024 Nobel Prize winner in Economics. In this intimate gathering, Robinson will discuss his influential book Why Nations Fail: The Origins of Power, Prosperity, and Poverty and explore the forces that shape nations, institutions, and global prosperity.

Guests will have the rare opportunity to engage directly with one of the world's leading economic thinkers in a personal, small-group setting, an experience typically reserved for academic and global policy circles.

Event to take place at BottlesUp! Wine Shop in Lakeview for up to 20 people, with 5 wines to taste with insights from the owner and light hors d'oeuvres (courtesy of Matt Reilein and Lizzy Whitehorn).

Date and times to be determined by mutual agreement.

Kiawah Island Luxury Retreat - 7 Nights of Coastal Elegance

Enjoy a week-long stay in a stunning 4-bedroom, 4.5-bath home on beautiful Kiawah Island, comfortably sleeping 10 guests, perfect for a family getaway or friends' escape.

This expansive home is designed for connection and relaxation, featuring a chef's kitchen for memorable family dinners and a private plunge pool ideal for unwinding after sun-filled days.

Golf lovers will appreciate the proximity to Turtle Point Golf Course, plus three additional public courses on the island, including the legendary Ocean Course, host of the 2021 PGA Championship.

The beach is just a 5-minute bike ride or 15-minute walk away, making daily ocean strolls effortless. Back at the house, enjoy ping pong, foosball, Xbox, and more!

Whether you're envisioning beach mornings, championship golf, or sunset dinners by the pool, this Kiawah retreat offers the perfect blend of luxury and leisure.

Booking Details:
-Subject to availability
-Not available during holiday weeks
-No June-August bookings
-Suggested dates: Fall months or HPDS Spring Break 2027 (March 22-March 26, 2027)
-No pets, no smoking
-Early booking strongly encouraged

Your coastal escape awaits.

Martha's Vineyard Coastal Escape - 7 Nights in Vineyard Haven

Experience the charm of New England with a 7-night stay in beautiful Martha's Vineyard, just steps from the beaches and the shops and restaurants of downtown Vineyard Haven.

This inviting home features three spacious bedrooms, including a newly remodeled first-floor primary suite with private bath, plus 1.5 additional bathrooms. Enjoy a large living room, bright sunroom, and a fully equipped kitchen with dining area, perfect for gathering after sun-filled days.

Step outside to a generous private deck ideal for al fresco dining and relaxing, surrounded by the timeless beauty of the Vineyard. AC, WiFi, and Cable TV are all included for effortless comfort.

Walk to the beach in the morning, stroll into town for coffee and boutique shopping, and return home for sunset dinners on the deck - this is Vineyard living at its best.

Available Dates (2026):
-April 19 - May 16
-September 20 - October 17
(Pending availability; booking arranged directly with donor)

Additional Details:
-$400 cleaning fee required
-$500 refundable damage deposit required

A quintessential island getaway awaits.

Private Lakefront Retreat - Keeler Lake, Michigan (Sleeps 20!)

Gather your crew for an unforgettable 7-night stay on 180 feet of private lakefront at Keeler Lake in Decatur, Michigan, complete with a pontoon boat included.

This spacious 5-bedroom home with 14 beds sleeps up to 20 guests, making it the ultimate destination for multi-family vacations, friend reunions, or summer memories with cousins and grandparents alike.

Set on a double lot along a beautiful 90-acre full-sport lake, the home features full kitchens on both levels, ideal for hosting large groups with ease. The walk-out lower level opens directly to the lake, with a large patio perfect for morning coffee or sunset cocktails.

Enjoy evenings around the outdoor fire pit (firewood included!), and take advantage of year-round mosquito treatments that significantly reduce those pesky summer bites.

Spend your days boating, swimming, fishing, and relaxing, this is classic Michigan lake life at its best.

Prime Summer 2026 Dates (Winner must confirm with donor by 3/31/26):
-June 22-29, 2026,
-June 29-July 5, 2026
-July 24-31, 2026

Spring and Fall dates offer greater flexibility and can be scheduled directly with the donor.

Stay must be used by May 15, 2027.

Lake Michigan Luxury Estate - White Pearl Beach (Sleeps 18)

Enjoy an unforgettable 3-night stay at this spectacular Harbor Country estate located on the stunning shores of White Pearl Beach along Lake Michigan.

This expansive retreat accommodates up to 18 guests across a beautifully designed main house and guesthouse, offering space, privacy, and breathtaking lake views at nearly every turn.

Enjoy direct access to one of the area's most beautiful stretches of shoreline, along with a heated pool (85-87°), two hot tubs (one available year-round), private tennis court, and outdoor fire pit, delivering a true private-resort experience.

Inside, the recently remodeled main house features vaulted ceilings, expansive windows, and elegant Italian furnishings in a bright, modern design that maximizes its lakefront setting. The luxurious primary suite includes a private balcony, jacuzzi tub, sauna, double shower, and skylight. Multiple king and queen en-suite bedrooms ensure comfort and privacy for all.

The separate guesthouse overlooks the tennis court and includes its own kitchen, living area, and additional bedrooms, ideal for extended family or teens.

Family-friendly amenities include gated stairs, baby gear, bikes, trampoline, beach chairs and towels, lake toys, and more. Up to 2 dogs (under 40 lbs) are welcome.

Additional Details:

The winning bidder may select a mutually agreeable three-night stay during March or April 2026, subject to availability. Dates will be coordinated directly with the donor. To allow flexibility in scheduling, availability must be confirmed in advance. A required $500 cleaning fee must be paid directly to the donor prior to check-in.

With private beach access on White Pearl Beach and room for everyone you love, this Lake Michigan estate offers the ultimate retreat.

Telluride Holiday Ski Week - Mountain Village Luxury (4BR, Ski-In Location)

Spend an unforgettable holiday week in Telluride with a 7-night stay in a stunning 4-bedroom, 4.5-bath Mountain Village home, perfectly positioned on a green ski run.

Step outside and onto the slopes, this privately owned villa offers true ski-access convenience and is just a short walk to the free gondola connecting Mountain Village to the Telluride ski mountain and the charming town of Telluride.

After a day on the mountain, unwind in your private outdoor hot tub, take in crisp alpine air, and gather with family and friends in a luxurious mountain setting during the most magical time of year.

With four spacious bedrooms and 4.5 baths, this home provides comfort and privacy for your group while placing you in the heart of one of Colorado's most iconic winter destinations.

Holiday Week Options:
-December 20-27, 2026
-December 27, 2026-January 3, 2027

Winner must select dates by April 1, 2026.

A ski-in holiday retreat in Telluride, this is peak-season mountain luxury at its finest.

Cap Cana Caribbean Escape - 7 Nights in Paradise (Sleeps 8)

Enjoy a luxurious 7-night stay in breathtaking Cap Cana, Dominican Republic, one of the Caribbean's most exclusive beachfront communities, just 20 minutes from Punta Cana International Airport.

This stunning 3-bedroom, 3+ bath beach- and pool-front condo comfortably sleeps 8 and is perfectly situated on the marina, offering serene water views and effortless access to both relaxation and adventure.

Recently renovated, the condo features a modern kitchen and a spacious private balcony, ideal for sunrise coffee overlooking the marina and sunset cocktails in the warm Caribbean breeze.

Cap Cana is known for its pristine white-sand beaches, turquoise waters, world-class fishing, island-hopping excursions, and family adventure parks. Golf enthusiasts will appreciate access to the acclaimed Punta Espada Golf Club (green fees not included).

An on-site concierge is available to assist with restaurant reservations and experiences, while grocery stores and shopping are just 10 minutes away, providing both convenience and comfort throughout your stay.

Availability:
-Thanksgiving
-Christmas / New Year's
-Anytime after May 1

-Availability by mutual agreement with donor, subject to availability.

Whether you're planning a holiday escape or a summer getaway, this Cap Cana retreat delivers a seamless Caribbean experience.

This vibrant, one-of-a-kind piece of neurographic art was created in collaboration by students across all three HPDS campuses, celebrating the creativity and unique minds that make Hyde Park Day School so special.
Inspired by the five sections of the brain and based on MRI scans of dyslexic brains, the abstract shapes flow together to form a playful and dynamic composition that reflects the complexity, curiosity, and individuality of how our students think and learn. Each colorful section contains layered marks and textures contributed by students, making every shape a small window into their imagination.
Special thanks to Elise Kendrot, Lemont parent and project creator, for designing and guiding this beautiful collaboration, with the assistance of HPDS art teachers Catherine Phelps and Chris Rinchich.

Own a signed copy of Semi-Well-Adjusted Despite Literally Everything by Alyson Stoner. In this candid and powerful memoir, Stoner reflects on identity, resilience, and navigating life in the spotlight, and has recently begun speaking openly about their experience with dyslexia. A meaningful and inspiring addition to any collection, especially for those who believe every learner deserves to be understood and supported.

Own a signed copy of Lovely Stuff, the 2025 release from Chicago punk favorites Smoking Popes, autographed by drummer Mike Felumlee. For fans of raw lyrics, driving melodies, and local music history, this signed album is a true collector's piece.

Enjoy an unforgettable night of NBA action with two (2) premium tickets to see the Chicago Bulls from one of the best seats in the house.

These lower-level seats are located directly behind the visitors' bench in Section 121, Row 3 (Seats 15 & 16), offering an incredible up-close view of the game and all the action on the court. The package also includes a VIP parking pass to make game day even easier.

Tickets are valid for a mutually agreed-upon game during the 2026-2027 NBA season, once the official schedule is released.

Catch the fast-paced excitement of the Chicago Blackhawks with four (4) prime lower-level tickets at the United Center.

Seats are located in Section 113, Row 9 (Seats 1-4) on the blue line, offering excellent sightlines to the ice and an ideal view of the action at both ends. This package also includes a VIP parking pass for added convenience on game night.

Tickets are valid for a mutually agreed-upon game during the 2026-2027 NHL season, once the official schedule is released.

Celebrate your pet(s) with a custom portrait experience designed to capture their unique personality and spirit.

This experience includes a dedicated portrait session, resulting in a finished custom pet portrait along with a digital image, perfect for framing, sharing, or gifting. Whether playful, dignified, or delightfully quirky, this portrait will be a lasting keepsake for any pet lover.

Celebrate your family with a professional portrait experience thoughtfully designed to create a lasting keepsake.

This experience includes a creative planning session, a professional photo shoot, and a beautifully matted finished portrait, along with a matching digital file for easy sharing and future prints. Thoughtfully planned and expertly photographed, this session results in a portrait your family will treasure for years to come.

Give your student the chance to step into the shoes of their campus leader for an unforgettable day! As Northfield Principal for a Day, your child will enjoy a behind-the-scenes look at how the school runs, help lead the day for the campus community, and take part in special responsibilities alongside the Northfield principal. The experience will include a 1:1 lunch meeting with Mr. Stieper, offering an opportunity to learn about leadership, decision-making, and the path to becoming a school leader.

This experience is perfect for any aspiring leader or curious student.

This item is for the Northfield Campus.

Give your student the chance to step into the shoes of their campus leader for an unforgettable day! As Chicago Principal for a Day, your child will enjoy a behind-the-scenes look at how the school runs, help lead the day for the campus community, and take part in special responsibilities alongside the Chicago principal. The experience will include a 1:1 lunch meeting with Ms. Newsome, offering an opportunity to learn about leadership, decision-making, and the path to becoming a school leader.

This experience is perfect for any aspiring leader or curious student.

This item is for the Chicago Campus.

Give your student the chance to step into the shoes of their campus leader for an unforgettable day! As Lemont Principal for a Day, your child will enjoy a behind-the-scenes look at how the school runs, help lead the day for the campus community, and take part in special responsibilities alongside the Lemont principal. The experience will include a 1:1 lunch meeting with Ms. Imboden, offering an opportunity to learn about leadership, decision-making, and the path to becoming a school leader.

This experience is perfect for any aspiring leader or curious student.

This item is for the Lemont Campus.

Enjoy a memorable wine tasting experience for up to six (6) guests at Lynfred Winery, a longtime Chicagoland favorite known for its wide variety of handcrafted wines and inviting atmosphere.

This experience includes a wine tasting certificate for your group, offering the chance to sample several of Lynfred's thoughtfully produced wines in a relaxed, welcoming setting. The package also includes Lynfred Winery merchandise to take home as a keepsake.

Whether you're gathering friends for a fun night out, celebrating a special occasion, or gifting an experience to a wine lover, this tasting is a wonderful way to enjoy great wine and great company.

Enjoy an unforgettable evening of world-class jazz at Ravinia's new intimate indoor venue, the Sandra K. Crown Theater. This exclusive package includes two tickets to see Grammy-winning vocalist Kurt Elling joined by legendary pianist and composer Fred Hersch for a stunning night of jazz duets on June 7, 2026.

Your experience goes beyond the performance with special backstage access and a VIP photo opportunity, offering a rare behind-the-scenes moment with these extraordinary artists.

Enjoy an unforgettable evening of world-class jazz at Ravinia's new intimate indoor venue, the Sandra K. Crown Theater. This exclusive package includes two tickets to see Grammy-winning vocalist Kurt Elling joined by legendary pianist and composer Fred Hersch for a stunning night of jazz duets on June 6, 2026.

Your experience goes beyond the performance with special backstage access and a VIP photo opportunity, offering a rare behind-the-scenes moment with these extraordinary artists.

Experience an unforgettable night of Chicago jazz history at the legendary Green Mill. This extraordinary package includes a reserved table for four (4) on April 25 as Grammy-winning vocalist Kurt Elling returns to his home club to celebrate the opening of International Jazz Week.

Reserved seating at the Green Mill is virtually unheard of, typically available only to the artist's personal guests, with fans lining up hours in advance for a chance at a table. You and your guests will instead arrive just 30 minutes before showtime and be personally escorted to your table for an intimate, once-in-a-lifetime evening of world-class music.

Drinks not included.

A truly rare opportunity for jazz lovers and anyone who appreciates an iconic Chicago night out.

Elevate your game with three private one-hour tennis lessons at The Racquet Club of Lake Bluff. Whether you're perfecting your serve or just getting started, personalized instruction at this premier North Shore club is the perfect way to sharpen your skills and enjoy time on the court.

Set sail for an unforgettable evening aboard a 46' Beneteau for a private 3-4 hour dinner cruise along the Chicago skyline. Departing from Burnham Harbor, this intimate experience comfortably hosts 4-6 guests and includes dinner and drinks as you take in the city at golden hour.

No sailing experience needed, just relax, unwind, and enjoy breathtaking skyline views as the sun sets over Lake Michigan.

Available on mutually agreed-upon dates in August or September.

Cheer on Chicago's home teams with this exciting soccer package!

Enjoy four (4) tickets to a 2026 match with Chicago Stars FC and four (4) Club Level tickets to a 2026 match with Chicago Fire FC, offering fantastic views and an elevated game-day experience.

Before or after the match, fuel up with a $100 gift card to Hattie B's, Chicago's go-to spot for legendary Nashville hot chicken and Southern comfort favorites.

Whether you're rallying behind world-class women's soccer or experiencing MLS action from premium club-level seating, this package delivers two unforgettable game-day experiences- plus a delicious meal to complete the outing. Perfect for a family outing, client entertainment, or a fun night out with friends.

Package 1 of 2

Host an unforgettable evening with a private, in-home wine sampling party for up to 12 guests, led by a wine consultant from PRP Wine International.

Enjoy a curated tasting of 8 bottles of wine while learning about flavor profiles, pairings, and regions, all from the comfort of your own home. Perfect for a girls' night, couples' gathering, birthday celebration, or client appreciation event.

An effortless, elevated way to entertain.

Package 2 of 2

Host an unforgettable evening with a private, in-home wine sampling party for up to 12 guests, led by a wine consultant from PRP Wine International.

Enjoy a curated tasting of 8 bottles of wine while learning about flavor profiles, pairings, and regions, all from the comfort of your own home. Perfect for a girls' night, couples' gathering, birthday celebration, or client appreciation event.

An effortless, elevated way to entertain

Package 1 of 2

Take your guests on a global journey without leaving home. Enjoy a curated 5-bottle wine tasting experience featuring selections from wine regions around the world, designed for up to 18 guests.

A dedicated Wine Advisor will coordinate your experience and ensure the wines are personally delivered to your front door. Wine glasses for the tasting are included, just invite your friends and enjoy an elevated, educational, and effortlessly hosted evening.

Winner pays a $22 handling fee.

Package 2 of 2

Take your guests on a global journey without leaving home. Enjoy a curated 5-bottle wine tasting experience featuring selections from wine regions around the world, designed for up to 18 guests.

A dedicated Wine Advisor will coordinate your experience and ensure the wines are personally delivered to your front door. Wine glasses for the tasting are included, just invite your friends and enjoy an elevated, educational, and effortlessly hosted evening.

Winner pays a $22 handling fee.

Gather your friends and indulge in a Lux Wine Tasting for four at Cooper's Hawk Winery & Restaurant.

Enjoy a guided tasting experience featuring a curated selection of wines in a warm, inviting setting. Whether you're celebrating, planning a girls' night, or simply love discovering new favorites, this experience offers the perfect blend of sophistication and fun.

Package 1 of 2

Enjoy America's pastime with four Outfield Reserve tickets to see the Chicago White Sox at Guaranteed Rate Field.

Valid for a Monday-Friday White Sox home game during the 2026 regular season, this package is perfect for a summer evening outing with family, friends, or clients. Take in the skyline views, ballpark classics, and the excitement of Chicago baseball from great seats in the outfield.

Package 2 of 2

Enjoy a classic Chicago baseball outing with four tickets to a 2026 regular season home game to see the Chicago White Sox at Guaranteed Rate Field - plus a parking pass included for added convenience.

Valid for any 2026 regular season home game (excluding Playoffs and Crosstown Classic games). Date to be mutually agreed upon with the donor. Winner should contact the donor at least two weeks prior to the desired game to allow time for purchase and delivery.

Gather your family or friends and enjoy a summer evening of baseball, ballpark favorites, and Chicago tradition.

Experience the power and artistry of Alvin Ailey American Dance Theater with two tickets to a performance at the historic Auditorium Theatre between April 24-26, 2026 (winner selects date).

Renowned worldwide for breathtaking choreography and iconic works like Revelations, Alvin Ailey delivers an unforgettable evening of movement, music, and emotion. A sophisticated night out in one of Chicago's most beautiful theaters.

Enjoy a magical live theatre experience with four tickets to a Theatre for Young Audiences (TYA) production at the acclaimed Marriott Theatre.

Perfect for families, these engaging productions are designed to delight young viewers while captivating audiences of all ages. Share the joy of storytelling, music, and live performance in an intimate, welcoming setting.

A wonderful outing for parents, grandparents, and children alike.

Bring the gym home with a Best Fitness Recumbent Bike, designed for comfortable, low-impact cardio workouts. Featuring a supportive seat and user-friendly console, this bike offers a smooth ride that's ideal for all fitness levels.

Perfect for improving endurance, supporting joint-friendly exercise, or simply staying active year-round from the comfort of home.

A practical investment in your health and wellness.

Cheer on the hometown team with two tickets to a 2025-26 season game featuring the Chicago Wolves at Allstate Arena.

Experience the fast-paced excitement of professional hockey in an electric, family-friendly atmosphere. A perfect winter night out for sports fans of all ages.

Game date to be mutually agreed upon

Enjoy two tickets to South Pacific at the stunning Paramount Theatre (April 29-June 14, 2026)

This beloved Rodgers & Hammerstein classic features unforgettable songs and sweeping storytelling, brought to life in one of Chicagoland's most beautiful historic theatres. A perfect date night or evening out for musical theatre lovers.

Performance date to be mutually agreed upon.

Make a splash with a Summer 2026 Family 4-Pack of Single Splash Tickets to WhoaZone at Whihala Beach.

This inflatable on-the-water obstacle course delivers climbing walls, slides, balance beams, and big jumps, all set along the beautiful Lake Michigan shoreline. Perfect for adventurous families looking for an unforgettable summer day of sun, laughter, and high-energy fun.

Valid for Summer 2026 season (single splash sessions).

Join us for an exclusive Private Shopping Night at Krista K Boutique!

Wednesday, May 6 | 6:00-8:00 PM
3458 N. Southport Ave
Limited to 20 guests | $100 per ticket

Enjoy an evening of shopping, sips, and style in a relaxed, after-hours setting. Your ticket secures access to this intimate event, and Krista K will donate 20% of all sales back to Hyde Park Day School.

Grab a friend, enjoy a glass of bubbly, and refresh your spring wardrobe while supporting HPDS.

Capture a precious moment forever with a weekday family portrait sitting at Classic Kids Photography.

This experience includes a professional portrait session and a $140 artwork credit to be used toward the purchase of custom artwork following your shoot. Create timeless images of your family that will be treasured for years to come.

Weekday session required. Additional artwork available for purchase.

Celebrate your four-legged family member with a weekday pet portrait sitting at Classic Kids Photography.

This experience includes a professional portrait session and a $140 artwork credit to be used toward custom artwork following your shoot. Capture your pet's personality in timeless, professionally crafted images perfect for your home.

Weekday session required. Additional artwork available for purchase.

Take home a signed copy of Being Henry: The Fonz...and Beyond, the deeply personal memoir by beloved actor Henry Winkler. Known worldwide as "The Fonz," Winkler has also been candid about his lifelong journey with dyslexia and the challenges he faced in school before finding his voice and confidence. His story of resilience, perseverance, and success beautifully reflects the power of believing in every learner. A meaningful addition to any bookshelf.

Enjoy a full year of natural beauty with a one-year dual membership to The Morton Arboretum.

This membership provides year-round access for two named adults to explore 1,700 acres of stunning landscapes, seasonal blooms, walking trails, exhibitions, and special events. From vibrant fall colors to spring blossoms and winter serenity, the Arboretum offers a peaceful retreat in every season.

Serve up summer fun with one week of Junior Tennis Half-Day Summer Camp at Tennis on the Lake.

Designed for young players of all skill levels, this engaging program combines professional instruction, skill development, and active outdoor fun in a supportive environment. Campers build confidence, improve technique, and enjoy time on the court with peers, all while staying active during summer break.

A fantastic way to strengthen skills, make friends, and enjoy a week of summer on the courts.

Gather your crew for the ultimate Wrigleyville outing with six bleacher tickets to see the Chicago Cubs at iconic Wrigley Field - plus $200 to Hattie B's Hot Chicken - Chicago, located right at Gallagher Way.

Winner will have choice of game (regular season, subject to availability). Enjoy an unforgettable day of baseball, ballpark energy, and a pre- or post-game feast in the heart of Wrigleyville.

Six seats. Great food. Your pick of game. This is Chicago summer done right.

Experience Cubs baseball in comfort and style with four tickets to the Catalina Club at historic Wrigley Field to see the Chicago Cubs.

Enjoy a climate-controlled indoor lounge, premier seating, and complimentary food and beverage included throughout the game. Winner will select from a handful of available regular season games (subject to availability).

An elevated, all-inclusive way to experience one of Chicago's most iconic traditions.

Celebrate big with a Private Table 10-Jumper Package at Altitude Trampoline Park - West Chicago, paired with a sweet treat from Crumbl Cookies.

This high-energy party experience gives 10 jumpers access to wall-to-wall trampoline fun in a reserved private table setting - perfect for birthdays or group celebrations. Top it off with a $50.00 Crumbl Cookie gift certificate to make the celebration even sweeter.

Easy to plan. Impossible not to love.

Make waves with a party for up to 24 kids at Goldfish Swim School - Evanston.

Enjoy private pool time in a warm, tropical-themed environment designed just for kids, plus dedicated party space for celebrating afterward. It's the ultimate splash-filled birthday experience, perfect for year-round fun (no weather worries!).

An easy, high-energy celebration that kids will never forget.

Join us for a private swim party for up to 45 swimmers at Goldfish Swim School - Evanston!

Saturday, April 25
4:30-6:30 PM

Enjoy private pool access in a warm, tropical environment, all while spending time with HPDS families from all campuses! The party includes pizza and cupcakes, making it an easy, high-energy, no-cleanup celebration.

Spots are limited, don't miss out!

Enjoy a one-night stay at the renowned Midtown Athletic Club, Chicago's premier wellness and lifestyle destination. This upscale retreat combines boutique hotel comfort with world-class amenities, including a state-of-the-art fitness center, indoor and outdoor pools, spa facilities, and exceptional on-site dining.

Whether you're planning a relaxing staycation, a wellness reset, or a special night out in the city, this experience offers the perfect blend of luxury and rejuvenation.

Subject to availability. Blackout dates may apply.

Package 1 of 2.

Create a timeless heirloom with a commissioned 14-inch fine art canvas portrait from Sanders Fine Portraits. This bespoke experience includes a personalized portrait session and a beautifully crafted canvas finished with hand artistry.

Known for their elegant, museum-quality portraiture, Sanders Fine Portraits captures the heart and personality of your family in a way that will be cherished for generations. This is more than a photograph, it's a legacy piece for your home.

Session scheduling subject to availability. Additional upgrades may be available.

Package 2 of 2.

Create a timeless heirloom with a commissioned 14-inch fine art canvas portrait from Sanders Fine Portraits. This bespoke experience includes a personalized portrait session and a beautifully crafted canvas finished with hand artistry.

Known for their elegant, museum-quality portraiture, Sanders Fine Portraits captures the heart and personality of your family in a way that will be cherished for generations. This is more than a photograph, it's a legacy piece for your home.

Session scheduling subject to availability. Additional upgrades may be available.

Enjoy three months of family membership at Lakeshore Sport & Fitness - Chicago's premier athletic club - plus a pickleball or platform tennis party for up to 16 guests!

This package offers full access to exceptional fitness facilities, pools, classes, and family programming, along with a private pickleball celebration perfect for friends, neighbors, or a birthday gathering.

Get active, get social, and make it a season to remember.

Membership valid September-May only. Subject to availability.

Enjoy one week of summer camp at Camp Galileo!

Camp Galileo blends engaging STEAM projects, collaborative design challenges, and classic camp traditions like silly skits, face painting, and even pie throwing. Every hands-on activity and outdoor game is thoughtfully designed by educators, tailored by grade level, and calibrated for both maximum fun and meaningful learning.

Give your child a summer experience filled with creativity, confidence, and unforgettable memories.

Valid for the 2026 summer season. Subject to availability.

Inspire imagination and hands-on fun with this thoughtfully curated Creativity Basket - perfect for budding artists, crafty kids, or anyone who loves to make something beautiful.

This bundle includes two $50 Michael's gift cards to stock up on supplies, plus an exciting assortment of art materials to start creating right away. Explore 50 vibrant colors of polymer clay, a full 39-piece paint set, quality Strathmore 400 Series sketchbook, colorful markers, and a stunning mandala rock art kit designed for mindful creativity.

Whether it's painting, sketching, sculpting, or crafting, this basket offers endless opportunities for artistic expression, with something for every medium and mood.

Everything you need for the ultimate outdoor day, packed and ready to go.

This fully stocked picnic backpack (complete with plates, silverware, wine key, and blanket) sets the stage for effortless family fun. Spend the afternoon flying a large Easy Flyer kite, launching stomp rockets, playing beach soccer, volleyball, frisbee, and backyard catch - all included in this action-packed bundle designed to get everyone outside and moving.

For the grown-ups, enjoy two exceptional bottles:
-Billecart-Salmon Brut Reserve Champagne
-Domaine de la Solitude Chateauneuf-du-Pape

And to top it off, you'll receive a $150 gift certificate to the beautiful Chicago Botanic Garden, perfect for a scenic stroll, seasonal blooms, and a peaceful family outing.

Whether it's a park day, beach afternoon, or backyard celebration, this basket delivers fresh air, fun, and a little luxury.

Your all-access pass to unforgettable family adventures.

This experience-packed bundle includes a $100 gift card to Funtopia for climbing and active fun, plus a $100 gift card to Puttshack for high-tech mini golf and laughs for all ages. Cool down afterward with a $50 gift card to Oberweis Dairy for ice cream and sweet treats.

The fun continues at home with a glow stick party pack and the classic UNO card game, perfect for family game night.

And for the adults? A special bottle of Chateauneuf-du-Pape to enjoy while the memories are being made.

Adventure, play, dessert, and a little something for the grown-ups - this passport covers it all.

Tee up for the ultimate golf getaway, on and off the course.

This impressive golf bundle is packed with premium gear and gift cards to elevate every part of your game. Enjoy a $125 Play Golf gift card, plus $50 gift cards to Dick's Sporting Goods, Bass Pro Shops, and Nike to upgrade your apparel, equipment, or accessories.

Hit the range in style with TaylorMade golf balls, a Callaway golf hat, performance tees, a GolfScrub, and a Driving Range 2-Flag Set to sharpen your short game. Stay refreshed with an Owala water bottle, and bring the energy with a Heyday wireless speaker for practice sessions or post-round relaxation.

Keep the fun going at home or in the office with a Mini Desktop Golf Pen Set and Desktop Mini Golf game. And when you're ready for a high-energy outing, enjoy a Topgolf package featuring a $50 off gameplay certificate plus four $25 gift cards.

Whether you're a serious golfer or just in it for the fun, this package is truly a hole-in-one.

Uncork, indulge, and elevate your evenings with this thoughtfully curated Wine Down basket, a sophisticated pairing of premium wine, artisan chocolate, and an unforgettable night out.

This indulgent collection features a decadent artisan assortment from ORO Chocolate, including six signature chocolate bars ranging from 62% to 88% cacao, a bold 100% dark drinking chocolate, and cacao husk tea for a refined sipping experience. It's a true tasting journey for chocolate lovers.

Complementing the sweets are three distinctive wines: Familia Deicas Atlántico Sur Albarino (Uruguay, 2024), Familia Deicas Extreme Roca Madre "Corte Único" (Uruguay, 2022), and Uno Malbec Platinum Edition Antigal (Mendoza, 2019), each selected to elevate any gathering or quiet evening alike.

The experience continues with $300 to City Winery, including $200 toward food and beverages and $100 toward show tickets. Enjoy an evening of live music, exceptional cuisine, and perfectly poured wine.

And to sweeten it all, six beloved Girl Scout Cookie classics - Thin Mints, Do-Si-Dos, Lemon-Ups, Samoas, Tagalongs, and Trefoils - round out this irresistible collection.

A thoughtfully curated collection for readers who love big ideas, meaningful stories, and a beautifully set reading moment.

This basket features two signed titles by renowned economist and political scientist James A. Robinson - The Narrow Corridor and Why Nations Fail - powerful explorations of freedom, power, and prosperity that spark rich discussion and reflection. Rounding out the collection are Theo of Golden by Allen Levi and Conform by Ariel Sullivan, offering compelling storytelling across genres.

Settle in with a luxuriously soft Lola blanket and your favorite warm beverage in a sleek Corkcicle mug, the perfect pairing for long reading sessions.

To keep the pages turning, enjoy a $100 gift card to Barnes & Noble and build your library even further.

Whether for your own nightstand or your next book club gathering, this basket is an invitation to slow down, think deeply, and savor every chapter.

Your journey to peak performance starts here.

This dynamic fitness package is built for anyone ready to level up their health routine, whether at home, in the gym, or on the court.

The highlight is a $230 gift certificate to FYT (Find Your Trainer), giving you the flexibility to choose your trainer and your venue - virtual or in-person - for professional coaching tailored entirely to your goals.

Track your progress with a sleek fitness watch designed to monitor your gains. Push your limits with a 12 lb weighted vest and 2 lb ankle weight set, and enjoy comfortable movement on an oversized 72" x 32" yoga mat that gives you the space you need to stretch and strengthen. A premium pickleball paddle set lets you jump into the fastest-growing sport in the country, while six pairs of grippy socks provide stability for every workout.

An invitation to slow down, recharge, and indulge in well-deserved relaxation.

This thoughtfully curated collection transforms any evening into a restorative retreat. Enjoy a handmade clay mug paired with three boxes of herbal tea, perfect for quiet moments of calm. A facial clay mask trio, luxurious bath bomb set, and Dr Teal's Epsom Salt and bubble bath collection create a full at-home spa experience, while a candle and reed diffuser set the tone with soothing ambiance. A bath caddy completes the scene, making long soaks even more indulgent.

The pampering continues beyond home with a $50 gift card to Tricoci Salon & Spa for nail services and a $120 gift card to Massage Envy for a restorative massage.

Whether you're gifting it or keeping it, this basket is a reminder that taking care of yourself is never a luxury, it's essential.

Bring the magic of the stage and screen home and out on the town.

This entertainment-packed basket features a $250 gift card to Broadway In Chicago, giving you access to world-class productions right in the heart of the city. Keep the cinematic fun going with a $100 gift card to Regal Cinemas and a $100 gift card to AMC Theatres, perfect for date nights, family outings, or blockbuster premieres.

At home, elevate your movie nights with two YETI beverage tumblers, a reusable ice and drink bucket, a movie trivia game for a little friendly competition, and an assortment of classic popcorn and snacks to complete the experience.

From Broadway lights to big-screen blockbusters, this basket is your all-access pass to unforgettable entertainment.

A curated culinary tour of the North Shore's favorite restaurants, breweries, and sweet spots.

Enjoy a $150 gift card to Double Clutch Brewing Company, plus a $100 gift card to Le Colonial for refined French-Vietnamese cuisine. Casual nights are covered with a $50 gift card to Taco Nano, $50 to Stormy's Tavern & Grille, $50 to Foxtail on the Lake, $50 to North Shore Pizza Company, and a $100 gift card to Francesca's.

Indulge your sweet tooth with a cupcake per week for six weeks from Three Tarts Bakery & Cafe - because dessert deserves its own spotlight.

And to elevate the experience, gather friends for a wine tasting for six at Lynfred Winery (valid at Wheeling, Highland Park, or Roselle locations).

From date nights to family dinners, brewery outings to wine tastings, this basket delivers months of memorable meals and shared experiences.

Elevate your hosting game with a beautifully curated charcuterie collection designed for effortless entertaining.

This basket includes a classic charcuterie board alongside an elegant marble serving board, complete with marble cheese knives and a set of Greyson spreaders for polished presentation. Chalkboard cheese markers add a thoughtful touch, making it easy to label every selection like a seasoned host.

Sweet and savory pairings are covered with specialty honey and a gourmet cranberry spread with coordinating spreader - perfect complements to cheeses, crackers, and more.

For inspiration, enjoy Boards: Stylish Spreads for Casual Gatherings and The Cheese Board Deck: 50 Cards for Styling Spreads, Savory and Sweet, offering creative ideas to design show-stopping displays for any occasion.

Whether you're planning a dinner party, wine night, or holiday gathering, this basket provides everything you need to serve with style and confidence.

Invest in your strength, confidence, and overall wellness with this exclusive training package from F.I.T. Boutique.

This package includes six (6) one-hour private personal training sessions tailored specifically to your goals, plus two (2) group fitness classes to keep you motivated and moving. Whether you're looking to build strength, improve endurance, refine technique, or jump-start a new routine, you'll receive expert coaching and individualized attention in a supportive boutique studio environment.

Indulge in a moment of pure relaxation with a $165 gift certificate to Milk + Honey Spa- Gold Coast, valid for one of their signature services. Whether you choose a rejuvenating facial, restorative massage, or another thoughtfully curated treatment, you'll experience the elevated care and serene atmosphere that make this spa a local favorite.

This certificate is valid exclusively at the Gold Coast location and may be applied toward one signature service. Subject to availability.

Treat yourself, or someone special, to a well-deserved escape.

Treat yourself to some of Chicago's most beloved dining experiences with this incredible culinary package.

Start by sharpening your skills in the kitchen with a $200 Sur La Table gift card, perfect for booking one of their hands-on cooking classes. Then explore some of the city's most popular restaurant groups with a $100 gift card to Four Corners Restaurant Group, $250 to Lettuce Entertain You Restaurants, and $250 to Ballyhoo Hospitality, each offering a wide variety of vibrant restaurants and dining concepts across Chicago.

Round out the experience with a $100 gift card to Riccardo's, a longtime Chicago favorite known for its classic Italian cuisine and welcoming atmosphere.

From learning new culinary techniques to enjoying unforgettable meals around the city, this package is a true Chicago dining adventure perfect for food lovers.

Take in Chicago from breathtaking new heights with this unforgettable skyline experience.

This package includes four (4) tickets to the iconic Centennial Wheel at Navy Pier and four (4) tickets to Flyover Chicago.

Ride the historic Centennial Wheel at Navy Pier, offering sweeping views of Lake Michigan and the city skyline from nearly 200 feet in the air.

Then continue the adventure with four (4) tickets to Flyover Chicago, an immersive flying theater experience that lifts you into the sky and carries you across Chicago's most spectacular landmarks through motion seating, wind, mist, and cinematic storytelling.

From the Ferris wheel to a thrilling aerial journey, this package lets you see Chicago like never before.

Purchase a bottle of wine from our wine pull and pick it up to take home with you at check-out.

Due to limited quantities, this item is only available for purchase by those in attendance at the gala.

Experience an unforgettable summer night at one of Chicago's most iconic venues.

This package includes two tickets to a 2026 concert at historic Wrigley Field, where you can choose from an incredible lineup including Mumford & Sons (June 11), Rufus Du Sol (June 12), Tyler Childers (July 12), or Noah Kahan (July 14-15).

Before the show, enjoy VIP access to the exclusive 1914 Club, one of Wrigley Field's most sought-after hospitality spaces, offering premium comfort, upscale amenities, and a perfect place to relax before and during the concert.

Complete the evening with $150 toward dinner at Alma at Hotel Zachary, the stylish restaurant just steps from Wrigley Field, ideal for cocktails and a delicious pre-show meal.

Music, VIP access, and a night out in Wrigleyville, this package is your ticket to an unforgettable Chicago summer.

Experience one of Chicago's hottest live music venues in VIP style.

Enjoy two VIP tickets to see St. Paul and the Broken Bones at The Salt Shed on May 1st, an electrifying night of powerhouse soul, brass, and unforgettable live performance.

Known for their explosive stage presence and rich, soulful sound, St. Paul and the Broken Bones deliver a show that fans and critics alike rave about. The Salt Shed - one of Chicago's most exciting concert venues - provides the perfect backdrop for an incredible night of live music.

Don't miss your chance to experience this unforgettable performance from VIP seats at one of the city's premier music destinations.