ENTER TO WIN!

Are you ready for the ultimate Chicago summer in 2026? After a long and cold winter, get ready for a hot and unforgettable season of wine tastings, live music, beach bars, hotel stays, sports, and live theatre!

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

or call (773) 281-8463 x126


Package includes:

Two-night stay at The Chicago Hotel Collection Ambassador Gold Coast

From Gold Coast views to deluxe amenities, this hotel is more than just a place to stay—it’s an experience. Includes:

  • Two (2) nights in a Junior King Suite
  • Two (2) daily complimentary breakfast coupons, two (2) complimentary drink vouchers, and $10 dinner credit
  • Blackout days apply; reservation based on availability at time of request
Wine Tasting Certificate for Six at Vin Chicago

Certificate for up to six wine lovers to attend any one of Vin’s “First Wednesday Wine Tastings” at Vin Chicago, 1826 North Elston Avenue. Monthly tastings happen on the first Wednesday of every month from 6:30pm – 8:30pm.

Four (4) Stellar Seats for the 2026 Chicago Cubs + Club Access

Valued at $2,000, this package includes four (4) tickets, parking pass, and access to the Maker’s Mark Barrel Club before/after the game. Good for Chicago Cubs vs. Atlanta Braves on Monday September 14, 2026 (Section 27, Row 7, seats 9-12).

Four (4) Stellar Seats for the 2026 Chicago White Sox + Club Access

Enjoy a great outing with family or friends with seats for four to see the Chicago White Sox. Package includes parking pass and access to The Stadium Club. Good for Chicago White Sox vs. New York Mets on Saturday, August 22, 2026 (Box 118, Row 6, Seats 5-8).

Two (2) tickets to the Tony Award-winning musical Suffs

Direct from Broadway comes the acclaimed Tony Award®-winning musical SUFFS, about the brilliant, passionate, and funny American women who fought tirelessly for the right to vote. Created by Shaina Taub, the first woman to ever independently win Tony Awards for Best Book and Best Score in the same season, this “thrilling, inspiring and dazzlingly entertaining” (Variety) new musical boldly explores the triumphs and failures of a struggle for equality that’s far from over. Winner of the Outer Critics’ Circle Award for Best New Musical. Good for performance at the CIBC Theatre on July 8, 2026 at 7pm.

Gift Certificate to Aura Beach Bar and Café

Happy Hour for two (2). Includes snacks and drinks.

One Night Pass to Grant Park Music Festival

Reserved seating section.

or call (773) 281-8463 x126


Winner will be drawn at TimeLine’s Inaugural Opening Night Gala on May 15, 2026.
Winner need not be present at the time of the drawing!
** Some restrictions apply **