I won free flights for a year

One important thing to do is, when you make your actual flight reservations, do a screen shot of the reservations purchase page and save it. Then when you file your tax return you can report the amount shown on the 1099-Misc but then subtract the difference between the $400 (or whatever) they say is the per-flight value and the actual value based on what it would have cost if you had purchased tickets. It may seem complicated, but it will save you a lot of money on your taxes.

It does work and is legal.

Mike (CPA Retired)
 
Congratulations on winning! That is an awesome prize to win, and, great of you to even having the thought of donating them! Most people wouldn't have even had that thought,so kudos to you, you will be truly blessed!
 
Just want to pop over and say congrats, and I admire your generosity! You'll bless someone beyond words with your donation, and selflessness!
 
Congrats! How exciting!
I would definitely focus on smaller charities. Generally these charities have lower overhead and little to no administrative costs, so your donation can do the most good.
I can recommend http://katyscourage.org/
Katy was a remarkable young girl who passed away too soon from a rare form of liver cancer. Google her name if you want to know more about this special girl, Katy Stewart. Her charity helps support pediatric cancer research, a scholarship in her name, and they are working on building a children's bereavement center to help children cope with loss.
Congrats again!
 

I just remembered listening to a story on the radio about this organization: http://www.bertsbigadventure.org/the-organization/. From their website:

Bert’s Big Adventure is a non-profit organization designed to allow children stricken with a chronic illness and/or physically challenged between the ages of 5 to 12 who prove financial need and live in the Bert Show radio listening areas, the opportunity to experience a magical weekend at Walt Disney World as the guests of the foundation.

Although it also looks like they charter a flight for the kids and family so I'm not sure if they could use the tickets?

Each year, the foundation (known as Bert’s Big Adventure) will take these children to Walt Disney World with their parents and siblings. Because of their special needs and financial strain, this is an experience that many of these children and families would not be able to experience without the help of the foundation.

The vision of the foundation is to charter a flight for these children, their families and a medical staff to Walt Disney World. While in Florida, the foundation will provide hotel accommodations, Walt Disney World park passes, transportation to and from the park, and meal coupons and spending cash for these guests of the foundation.
 
How wonderful for you!

There is an organization called "Honor Flight" that pays (through donations) for veterans to visit the Washington DC war memorials/monuments of the particular war they fought in. I know they take donations of airline miles/vouchers. The .org is the correct one that provides free flights for our veterans. The .com organization charges fees.

Btw--Southwest is the official carrier for this organization.

Hopefully you find an organization that is dear to your heart. What a great thing for you to do!

When we were stationed in DC my hubby was one of many military guys that helped when they came to visit. He loved it and meet so many WWII vets. I think they would love the help.
 
Charitable Donations cannot be claimed if you claim the standard deduction, only if you itemize your deductions. So, keep that in mind when considering what to do with the tickets.

To help offset the cost of the extra tax you will have to pay, you may want to consider modifying your w/holdings from your paycheck. While it wont lower your tax consequence in the end, it will help make it a bit more bearable.
 
Congrats and way to go! So thoughtful and generous of you to share with others in need.
 
Also to lessen the tax bill, if you can prove the flights you took were less than 400.00 you can claim that number, not the random 400.00 assigned to them.

You can, but the IRS will disallow it.

I won a similar prize several year ago. We got Disney Park Hoppers, nights at AKL, and airfare for four. I looked up the value of our flights and made a hard print copy showing what that flight was selling for 6 weeks out and the week of the trip. The IRS said that United had claimed a much higher value for the flights and I had to pay tax based on that number.

The good news about that is that OP will be able to claim a value of $400 per flight for any she gives away. Southwest/Subway have already declared that to be the value they spent for marketing so the value is established in the eyes of the IRS. (Since this is a happy board, I won't start in on United declaring they'd spent $$$ offering us flights they couldn't sell for $$.:cool1:)
 
I won 24 Southwest airlines green must fly passes from Subway recently.

It is an amazing prize and while I did use 5 of them to book our upcoming Disneyworld trip and gave 2 to my aunt so she can go visit my cousin who is coming home from Afghanistan soon I still have a few that I won't be able to use. It's wonderful to have free flights but as you all know you still have to pay for food, attractions, and possibly hotel where ever you go.

Anyhow, I was thinking of donating some of them (I can't sell them but I can give them away as I please) to help out with the tax bill I'll be hit with due to the win (almost $10,000 prize) southwest values the vouchers at $400 a piece ARV so I thought if I donated some of them it might help knock down the tax bill. Just wondering if anyone here may know how I would go about doing that? Charity suggestions? Not sure if you can donate flight vouchers or not but being this is the travel section thought someone may know. I'm going to post this in the budget board as well. Thanks.

Congrats on winning!

What about Make-A-Wish?
 















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