Risk-free consignment · Pay $0 unless it sells · TRV-CHI-001
Walking downtown · No hotel · No airfare
The Insider's Chicago Day for Your Charity Auction
What is The Insider's Chicago Day? It is a risk-free consignment auction package for nonprofits: a guided downtown walk for two, with The Bean, Loop landmarks, and a meal of Chicago classics. Hotel and airfare are not included. The nonprofit pays $499 only if the package sells. If it does not sell, the nonprofit owes nothing.
A guided downtown Chicago food and landmark walk for two. The Bean, Loop icons, and a full meal of Chicago classics.
About 4.5 hours and 3 to 4 miles on foot. Small-group walking tour (up to 12) with a local guide. Meet at The Chicago Theatre. Food tastings as offered that add up to a full meal. Concierge confirms the date and route. No hotel. No airfare. Guests should be comfortable walking 3 to 4 miles. This is not Ultimate Chicago Weekend and not Wrigley Rooftop VIP.
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
- Walking downtown Chicago experience for 2
- About 4.5 hours and 3 to 4 miles on foot
- Small-group walking tour (up to 12) with a local guide
- Food tastings as offered that add up to a full meal
- Landmarks as offered: Chicago Theatre, Pedway, Riverwalk, Wrigley Building, Tribune Tower, Millennium Park, and The Bean
- Concierge planning
What is not included
- Hotel or lodging. Optional at redemption
- Airfare and transport to Chicago
- Ride to or from the downtown meeting point
- Food and drinks beyond included tastings as offered
- Extra guests or experiences, tips, and travel insurance
Snapshot
- Guests2 guests. Walking afternoon. No hotel. No airfare.
- MeetMeet at The Chicago Theatre. About 4.5 hours. 3 to 4 miles on foot.
- Redeem12 months to redeem. 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 Ultimate Chicago Weekend (SPT-CHI-001). Not Wrigley Rooftop VIP (SPT-CHI-002). Not Insider's Chicago Weekend (TRV-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 Day 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: downtown landmarks, The Bean, and Chicago classics for two. Feels like a planned Chicago afternoon, not a coupon. Clear $900 value. Concierge fulfillment. You pay only if it sells. Not a Wrigley rooftop, van, or private tour.
Easy stage story
Downtown landmarks, The Bean, and Chicago classics for two. Clear $900 value.
Zero risk
You only pay $499 if it sells. If it does not sell, you owe nothing.
Concierge handled
We confirm the date and route. Meet at The Chicago Theatre.
Sell to all
Each accepted paddle is one package. You set the sell-to-all price. You pay $499 only per package sold. This is not a Wrigley rooftop package.
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?
- A guided downtown Chicago food and landmark walk for two. About 4.5 hours and 3 to 4 miles on foot. Small-group tour with a local guide. Food tastings as offered that add up to a full meal. Landmarks as offered include The Chicago Theatre, Pedway, Riverwalk, Wrigley Building, Tribune Tower, Millennium Park, and The Bean. Concierge planning. Hotel and airfare are not included.
- Is hotel included?
- No. Hotel is not included. Lodging is optional at redemption. Airfare and transport to Chicago are not included.
- How long / how much walking?
- About 4.5 hours. About 3 to 4 miles on foot. Guests should be comfortable walking that distance. Meet at The Chicago Theatre.
- 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.
- 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.
- How is this different from Wrigley Rooftop / Ultimate Chicago Weekend?
- This is a walking downtown food and landmark afternoon for two. No rooftop. No hotel. Wrigley Rooftop VIP is a hotel-free game-day rooftop package. Ultimate Chicago Weekend includes a hotel, rooftop, Uber, and a Loop pizza walk. Do not sell this as a Wrigley rooftop or hotel stay.
- 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 Day 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