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Shop, Dine, Save & Win

November 24 - December 31, 2023

Discover the joy of giving back this holiday season with the Shop, Dine, Save & Win initiative!

Created to encourage retail sales in Woodstock, this program not only saves you money on your purchases but also rewards you for supporting local small businesses.

Your participation in the "Shop, Dine, Save & Win Program" is a win-win.

Thanks to the generous sponsorship from the City of Woodstock, this holiday shopping extravaganza is managed for you by the Woodstock Area Chamber of Commerce & Industry.

Individuals who submit qualifying receipts from our unique independent retailers and restaurants get a instant $20.00 cash and stand a chance to win BIG!

The impact of your support is twofold: not only do you get a chance at winning exciting prizes totaling $1,900, you also get to share the joy with your favorite small retailer through a 50/50 split.

Qualifying receipts must be from at least two businesses and total a minimum value of $200 pre-tax.

Let's make this holiday season a celebration of community and economic vibrancy!

*Certain products and businesses may have exceptions regarding qualification. See additional rules for details.

  • Shop and dine with small independent retailers and restaurants in Woodstock (CLICK HERE  for list of eligible businesses) between November 24, 2023 and December 31, 2023 and spend $200 or more (pre-tax, exclusions apply).
  • Submit qualifying itemized receipts in-person only to the Woodstock Area Chamber office and Real Woodstock Visitor Center in the Old Courthouse Center at 101 N. Johnson St., Unit 1A, Woodstock, IL 60098.
    • Open daily: Monday-Friday 9am-5pm, Saturday 10am-4pm and Sunday 11am-4pm.
    • Holiday week schedule varies; please check website home page for holiday hours.
  • Qualifying entries must include itemized receipts from at least two (2) different eligible businesses and total a minimum of $200 pre-tax purchases.
  • All entries must be submitted by Friday, January 5, 2024 at 12:00 p.m.
  • All eligible entries will receive $20 cash at the time of submission.
  • Individuals may submit one (1) eligible entry. Must be 18 years of age to enter.
  • Complete a raffle entry form when you submit your receipts for a chance to win cash prizes to split with your favorite local retailer.
  • On your raffle entry, identify the Woodstock retailer you wish to split the prize money with, should you win.
  • Chamber/Visitor Center staff will verify, record and mark your accepted receipts.
  • Three winners will be selected:
    • First Prize $1,000
    • Second Prize $600
    • Third Prize $300
    • Prizes will be split 50/50 with winner and the eligible business they selected.
    • Winners will be drawn, and prizes announced on Tuesday, January 9, 2024.

This program is for residents and visitors who shop at our small independent brick and mortar retailers and restaurants only.

Not Eligible:

  • Receipts that are not itemized.
  • Receipts from big-box stores, grocery stores, auto, RV, motorcycle, boat, liquor, tobacco, gas, and convenient stores are not eligible.
  • Receipts from stores outside the corporate boundaries of Woodstock, Illinois.
  • Receipts dated before 11/24/23 or after 12/31/23.
  • Receipts from online stores that do not have a physical brick and mortar location in Woodstock. 
  • Receipts that include tobacco, alcohol, or gasoline. (Restaurant receipts must be itemized, to decipher food from alcoholic beverages - only food is eligible. Non-itemized food receipts will not be accepted.)
  • Receipts for services (including haircuts and colors), installation or delivery charges are not eligible.
  • Receipts for purchases made with gift cards.
  • Receipts for the puchase of gift cards.
  • Receipts & raffle entries submitted to the Woodstock Area Chamber after Friday, January 5, 2024 at noon.
  • Receipts sent via email, fax or postal mail.


  • Receipts from retailers and restaurants on the List of Eligible Small Independent Retailers and restaurants in Woodstock (if you believe we have missed a business please call the Chamber office (815) 338-2436 to request an addition)
  • Receipts from hair salons, barbershops and other combined service/product businesses for retail sales only, not services.
  • Online purchases, with receipts, from the list of eligible small independent brick and mortar businesses.
  • One entry per individual with qualifying receipts.
  • Receipts dated between 11/24/2023 and 12/31/2023. 
  • Receipts & raffle entries submitted to the Woodstock Area Chamber by Friday, January 5, 2024 at noon.

Prize recipients will receive check payments. A valid drivers license or other government-issued ID must be presented for prize pickup.

By participating in the Shop, Dine, Save, Win program, individuals agree their photo may be taken and used for promotional purposes.

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