The Maui Raffle


With TimeLine’s 2024 Step Into Time Maui Raffle, you could win a 7-night vacation in Maui for as little as $25!

Our Step Into Time Maui Raffle Prize includes:

  • Accommodations for 7 nights in a beautiful one-bedroom condo in Hawaii
  • $500 to use for airfare or spending money

Winner will be drawn at TimeLine’s Step Into Time benefit on March 16, 2024.
Winner need not be present at the time of the drawing!

or call (773) 281-8463 x126

Prize generously donated by
M. Elizabeth Zeigler

All net proceeds benefit the mission and programs of TimeLine Theatre.


Images of Maui

Experience ultimate relaxation in your own oceanfront hideaway.

Located in the heart of the Kaanapali – Kapalua area, where you can enjoy magnificent sunsets and a breathtaking view of Molokai.

We had a really fantastic time in this Western Maui location. Watch spectacular sunsets from the deck. Delight in the sea turtles frolicking in late afternoon. Settle back in relaxed accommodations. There is a real spirit of Aloha here. Easy access to all of Maui’s best. Snorkeling. Fine dining. Island food. Exploring the island. Sitting under a Plumeria Tree.  — Previous Step Into Time Raffle winners Robert Alpaugh and Rob Waters

Ideally situated near the center of all the activities that make this a world-famous vacation destination, this Maui condo is located in an intimate 2-story complex right at the oceanfront. Enjoy over 2 acres of lush tropical foliage, and a small secluded beach for snorkeling or just dipping your toes in the water. The perfect location for watching the resident turtles return at sunset. Being right at the water’s edge you may be treated to awesome whale shows from December to April.

Located in the center of popular Maui Resorts, this 1-bedroom 1-bath unit sleeps 4 and features all the amenities to make your time in paradise truly memorable, including a full kitchen, cable TV/VCR, stereo, beach equipment and even a sand pail or two. The condo complex also has a heated swimming pool and oceanfront deck with BBQ facilities and dining area.

It was like waking up every morning in paradise. Perfect weather everyday. Beautiful beaches everywhere. Stunning ocean views and scenery. Never would have survived the Chicago winter without the week-long respite in paradise.
— 2008 Step Into Time Raffle winners

PLEASE NOTE: Raffle ticket purchases are not tax-deductible. Winner’s travel must be completed by 3/16/25 and travel dates are subject to availability. Dates to be mutually agreed upon. Some restrictions apply.