Risk-free consignment · Pay $0 unless it sells · TRV-CHI-002
4 experiences · No hotel · Speakeasy 21+
The Insider's Chicago Weekend for Your Charity Auction
What is The Insider's Chicago Weekend? It is a risk-free consignment auction package for nonprofits: four experiences for two, including a river architecture tour, a Loop food walk, Willis Tower Skydeck, and a 21+ speakeasy tour. Hotel is not included. The nonprofit pays $499 only if the package sells. If it does not sell, the nonprofit owes nothing.
Four stacked Chicago experiences for two. River architecture, Loop food walk with deep-dish as offered, Willis Tower Skydeck including The Ledge, and a 21+ speakeasy walking tour. No hotel. No airfare.
A weekend-shaped stack for two in Chicago. Concierge books the dates and confirms meeting points. Experiences may spread across two days when calendars allow. Distinct from The Insider's Chicago Day (single day walk) and from Ultimate Chicago Weekend and Wrigley rooftop packages. Speakeasy guests must be 21 or older with a valid ID. Drinks on the cruise and at speakeasies are extra.
Example at opening bid: $600 - $499 = $101 net. Not a guarantee.
Free account. This package added. Pay $499 only if it sells.
Use the auction you already run. Our software, another site, an auctioneer, or paper bid sheets.
- Zero upfront cost
- Works with your auction
- No sales call
- Pay only if it sells

What guests see on the Display Sheet.
What is in this package?
What you get
- Four Chicago experiences for 2
- Architecture river cruise, about 1.5 hours, with a live guide
- Loop food walk, about 3 hours, with tastings as offered including deep-dish
- Willis Tower Skydeck including The Ledge
- Speakeasy walking tour. Guests must be 21 or older. Drinks are extra
- Concierge planning. May spread across two days
What is not included
- Hotel or lodging. Optional at redemption
- Airfare and transport to Chicago
- Rides between meeting points
- Drinks on the cruise and at speakeasies
- Extra food beyond tastings as offered
- Extra guests or experiences, tips, and travel insurance
Snapshot
- Guests2 guests. 4 experiences. No hotel. No airfare.
- Speakeasy21 or older with a valid ID. Drinks are extra.
- Redeem12 months to redeem. No extensions. About 60 days notice.
- Sell to allEligible. You set the price. Each paddle is one package. You pay $499 only per package sold.
- Not this itemNot Insider's Chicago Day (TRV-CHI-001). Not Ultimate Chicago Weekend (SPT-CHI-001). Not Wrigley Rooftop VIP (SPT-CHI-002).
How does this risk-free package work?
Create a free account. Add this package. Run it in the auction you already have. Pay only if it sells.
Create a free account and start your package list
Your package list is the group of packages you want in your auction. You do this yourself.
Add The Insider's Chicago Weekend and open the kit
Add this package. Then open the kit: listing copy, Display Sheet, scripts, and winner papers.
List it your way
List online, on paper, or with an auctioneer. Use our software, another site, or paper bid sheets. You do not have to switch platforms.
If it sells, enter winners
Enter the winners. We invoice the nonprofit cost. After you pay, we contact the winners.
Why chairs list this
Easy stage story: four named experiences, two guests, one concierge. Reads like a weekend without a hotel bill inside the nonprofit cost. Clear $1,200 value. Sell-to-all eligible. Say the speakeasy is 21+ from the stage and on the listing. Distinct from the single Chicago Day walk and from Wrigley. You pay only if it sells.
Easy stage story
Four named experiences for two. One concierge. Clear $1,200 value. Say the speakeasy is 21+ from the stage.
Zero risk
You only pay $499 if it sells. If it does not sell, you owe nothing.
Concierge handled
We book the dates and meeting points. Experiences may spread across two days.
Sell to all
Each accepted paddle is one package. You set the sell-to-all price. You pay $499 only per package sold.
Free account. This package added. Pay $499 only if it sells.
Kit preview
Everything you need to list this item. Download, print, and list.
Nonprofit Decision Guide
Cost, value, and why this item can raise money.
Item Listing
Copy and paste for an online auction or paper catalog.
Display Sheet
Print it for a table, easel, or wall.
Auctioneer Script and Brief
A full script, plus a short card for a pro.
Promotions Guide
Email, social, and night-of blurbs.
Organizer README
A simple runbook from setup to close.
Winner Certificate
A printable certificate you can hand to the winner.
Winner Stay Guide
What winners need after the auction closes.
Item images
Photos you can use in your listing.
Create a free account to open the full kit. No PDF links on this page.
Frequently asked questions
- What is included?
- Four experiences for two: an architecture river cruise, a Loop food walk with tastings as offered including deep-dish, Willis Tower Skydeck including The Ledge, a 21+ speakeasy walking tour, and concierge planning. Hotel and airfare are not included. Drinks on the cruise and at speakeasies are extra.
- Is hotel or airfare included?
- No. Hotel is not included. Lodging is optional at redemption. Airfare and transport to Chicago are not included.
- Is the speakeasy 21+?
- Yes. Speakeasy guests must be 21 or older with a valid ID. Drinks are extra.
- Is sell-to-all allowed?
- Yes. Each accepted paddle is one package. You set the final sell-to-all price. You pay $499 only per package sold.
- What is the nonprofit cost and when do we pay?
- $499 per package sold. You pay only if it sells. If it does not sell, you owe nothing. Never print nonprofit cost on bidder-facing Display or listing.
- How is this different from Chicago Day / Ultimate Chicago Weekend / Wrigley Rooftop?
- This is a four-experience hotel-free stack: river cruise, Loop food walk, Skydeck, and a 21+ speakeasy tour. The Insider's Chicago Day is a single downtown walking afternoon. Ultimate Chicago Weekend includes a hotel and Wrigley rooftop. Wrigley Rooftop VIP is a hotel-free game-day rooftop package. Do not mix these items.
- How long to redeem / notice needed?
- Within 12 months of auction close. No extensions. About 60 days notice is recommended.
- Do we have to use CharityAuctions software?
- No. Use our software, another auction site, paper bid sheets, or an auctioneer. You still create a free account so you can add the item, open the kit, and enter winners if it sells.
Add The Insider's Chicago Weekend to your package list
Free account. This package added. Pay $499 only if it sells. Use the auction you already run. Our software, another site, an auctioneer, or paper bid sheets.
Open my free account and get the kitBrowse all Risk Free packages