2026 Fall Benefit Raffle
Raffle winners will be drawn at the end of the 2026 Fall Benefit on September 24. 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 23. Raffle tickets will also be available for purchase in-person the evening of the Fall Benefit on Thursday, September 24.
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.
Exact dates of stay are to be determined with the owner; blackout dates apply.
Donated by Mike Miller
Value: $1,300
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.
Donated by Michael and Christina Collins.
Value: $800
Family Portrait or Headshot Session
This prize includes a one-hour photo session with Tone Stockenstrom, tailored to your choice of a family portrait session or a professional headshot shoot. You’ll receive stunning, high-resolution digital images through a convenient online gallery and download link to treasure for years to come.
Donated by Tone Stockenstrom
Value: $600
Night at the Steppenwolf Theater
Two (2) tickets for any performance of Topdog/Underdog in the 26/27 Subscription Season (excluding Saturday night and Sunday matinee), with a Tony Award-winning director, a Pulitzer Prize-winning script and a tour-de-force showdown for ensemble members Glenn Davis and Namir Smallwood.
Donated by Steppenwolf Theatre
Value: $179
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.
Donated by Desoto House Hotel
Value: $250
Afternoon for Two at the Checkout
Two (2) tickets for a Sunday matinee show at The Checkout, Chicago’s only chamber music venue in a former 7-Eleven and operated by Chicago-based nonprofit Access Contemporary Music. Two Sunday matinee shows per month featuring solo pianists performing classical music are available for voucher use.
Donated by The Checkout
Value: $75