2025 Fall Benefit Raffle
Raffle winners will be drawn at the end of the 2025 Fall Benefit on September 18. Entrants need not be present to win. Winners will be contacted via email. Each entrant is eligible to win one prize.
Raffle tickets are available for $25 each, or in bundles of 5 tickets for $100 or 30 tickets for $500.
Raffle tickets are available for purchase online until 5:00 PM on Wednesday, September 17. Raffle tickets will also be available for purchase in-person the evening of the Fall Benefit on Thursday, September 18.
Proceeds from raffle sales support all of CMSS’ programs and services, including affordable housing for seniors, assisted living memory care, personalized home care, and social and support programs that reduce loneliness and isolation. Thank you for supporting our important work!
**New prizes are still being added! Check back to see what else you could win!**
Four-Night Stay at Eagle Waters Resort
You could win a four-night stay at Wisconsin’s Eagle Waters Resort in a completely furnished, 3-bedroom, 3-bathroom condo. The condo includes a full kitchen, and dining options are located nearby.
You will also receive a guided kayaking trip for up to four (4) on the Wisconsin River.
Exact dates of stay are to be determined with the owner; blackout dates apply. Exact dates of kayaking trip must be coordinated with Hawk’s Nest Outfitters.
Donated by Mike Miller and Hawk’s Nest Outfitters.
Value: $1,600
Private Sightseeing Flight in Chicago
Have you ever wondered what your favorite Chicago landmarks look like from above? Have you always wanted to know what it is like to fly in a private plane?
With this prize, you will get the once-in-a-lifetime opportunity to board a private plane with up to four guests of your choice and explore our beloved city in a whole new way. This private sightseeing opportunity will let you experience the excitement of small plane travel in a TBM 930 plane.
You’ll take off for flight in Kenosha, WI. After landing, enjoy dinner and drinks at the Waterfront Warehouse, an upscale bar and grill nearby.
Donated by Michael and Christina Collins and Waterfront Warehouse.
Value: $1,040
A Night at the Lyric Opera
Photo: Civic Opera House by vxla. CC BY 2.0.
With this prize, you can enjoy a night at the opera with two tickets to a 2025 / 2026 Season show (some restrictions apply). You could see Medea, Cavalleria rusticana, & Pagliacci, or Salome. Before or after the performance, enjoy a meal nearby at Bar Mar with a $200 gift card.
Donated by Lyric Opera of Chicago and Anonymous.
Value: $750
iPad Mini and Accessories
Win an iPad Mini (A17 Pro) with Wi-Fi and 128 GB of storage. The iPad mini has everything there is to love about iPad in a light, compact design. The 8.3″ Liquid Retina display features True Tone, P3 wide color and ultralow reflectivity, making text sharp and colors vivid. This prize is accompanied by a Zagg Pro Stylus to use with the iPad mini and a Zagg Crystal Palace Case with Folio.
Donated by Paula Basta.
Value: $620
Two Tickets to the Cardinals @ Cubs Game
Photo: Wrigley Field 2018 – 42195054760 by Ryan Dickey, CC BY 2.0.
Cheer on the Chicago Cubs at the final regular season game of 2025 on Sunday, September 28. Game starts at 2:20 PM at the historic Wrigley Field. You and your guest will be seated just a few rows behind the dugout, with a great view of the field for what promises to be an excellent game.
Before or after the game, enjoy a meal at Mon Ami Gabi with a $200 giftcard.
Donated by QOROS and Lettuce Entertain You.
Value: $600
Weekend in Milwaukee
Enjoy a weekend trip to Milwaukee! You will receive a $200 gift certificate to Hotels.com. Find the right place for you in the city and enjoy all that Milwaukee has to offer. This prize includes six (6) tickets to the Pabst Brewing Company’s Best Place Pabst Beer History Tour.
Donated by Pabst Brewing Company.
Value: $300
55" Samsung Smart TV
This 55-inch 2025 Samsung Smart TV (model U7900F) offers optimal size, speed, and display. The TV comes with 4K, ultra-sharp visuals with vibrant colors, smooth motion, and built-in streaming apps.
Donated by Abt.
Value: $280
Galena Mini-Vacation
Photo: DeSoto House Hotel — 230 South Main Street Galena (IL) September 2015 by Ron Cogswell, CC BY 2.0. Edited.
This prize includes a one-night, mid-week (Sunday – Thursday) stay at Illinois’ oldest operating hotel – the DeSoto House Hotel. The DeSoto House Hotel is nestled in downtown Galena, near shops, restaurants, historic sites, and plenty of attractions and activities. You will also receive a giftcard to the local restaurant, Fried Green Tomatoes.
Donated by Desoto House Hotel and Fried Green Tomatoes.
Value: $255
Apple Watch SE
This Apple Watch SE offers essential health, fitness, and safety features like Fall Detection, heart rate alerts, and Emergency SOS, all in a stylish, swimproof design. It keeps you connected with calls, texts, music, and Siri when paired with your iPhone or Wi-Fi.
The new watch OS 11 system offers more personalization and seamless compatibility with Apple devices.
Value: $250
Volo Museum Visit
Photo: Public domain image accessed from Stated Island Kar Klub Inc. Flickr.
Win four tickets to the world-famous Volo Museum — home to one of the nation’s largest rotating collections of classic and modern collector cars, rare mechanical marvels, and family-friendly attractions like a massive animatronic dinosaur park.
Spanning over 60 acres, this unique destination offers unforgettable experiences for visitors of all ages!
Donated by the Volo Museum.
Value: $200
Four Tickets to a Chicago Fire FC Match
You and three (3) guests will receive Club Level tickets to any Chicago Fire FC home match during the 2026 regular Major League Soccer season. Cheer on the Chicago Fire with a great view of the game.
Some game exceptions apply.
Donated by the Chicago Fire FC.
Value: $200