Know-How Exchange : Other

1. Your question is best posed to an attorney who specializes in advertising/promotion law in Illinois. Your company lawyer may be able to refer someone.

2. From a marketing standpoint, who is your primary target audience? Are you reasonably certain the prize will be attractive to them? The travel incentive doesn't seem like a logical tie-in to the qualification for participation ... or am I missing something?

See if this helps:

https://gleam.io/blog/usa-giveaway-laws/

It is from Australia, but many/most of the concepts probably apply in the US.

Or use Bing:

Hello, this is Bing. I can help you with some information about sweepstakes and contests laws in Illinois. According to sweeppeasweeps.com, Illinois sweepstakes must be no purchase necessary, which means no payment to receive, use, compete for, or get written information about a prize. Contests are allowed as long as the sponsor awards the prize based on skill and not chance. Also, cannabis or any product containing cannabis, such as food or drinks are not allowed as prizes."

There's more, of course.

Some additional concerns:
• What if during the promotion period your get few jobs – so that the promotion would be a bottom line loss?
• Does the entrant have to completely pay for the work before they can be entered into the contest?
• Will the prize have a payout cash value (in case the winner doesn't want or can't take the trip)?

What you are planning is a sweepstake.

A few sites of interest. First one seems to compile the rules for the state in regular words most can understand:
https://www.sweeppeasweeps.com/sweepstakes-and-contest-rules-illinois/

This one provides general info (not state specific) on how to use a sweepstakes in marketing:
https://www.3tl.com/blog/how-sweepstakes-and-contests-drive-customer-acquis...

And this seems to be the wording of the (or on e of the) relevant IL laws:
https://www.ilga.gov/legislation/ilcs/ilcs3.asp?ActID=2362&ChapterID=67

Sweepstakes do need to be open to everyone. That means not just your customers who pay $25k or more. And legally the winner needs to be chosen at random (including from within the non-customers). There are (I believe - couldn't find reference, so you should double check this) ways to weight the chances towards a customer winning. 2 options that come to mind are:1) have customers earn multiple entries (say 1 entry per $1000 in purchases) where non-customers earn just 1 entry and 2) make it a bit harder for non-customers to enter, such as by having them mail in a post card (so they have to pay for a stamp) to enter. Not sure about the stamp being considered a purchase, so you might also need to have a box at your office they can put a card in. I think you can limit non-customers to 1 entry per person/address.

There are sweepstakes management companies out there, which might be worth hiring to ensure you do this right.