I did standy by last week so now i have a free Round Trip Flight on Alaska Airlines. I have to leave out of Chicago. I am not sure where i should go. Also, how is Alaska's policy on the Free Ticket i got, i hope they are pretty good with it.
I can go international too

If it were me, loving warm weather destinations like I do, I'd use it for Cancun and then get to somewhere like Isla Mujeres or the Mayan Riviera from there. I thought I read that they pull those seats from the FF inventory. Check flyertalk.com. They'd know. Have fun!

When do you want to go?

Blast up to Nome in time for the mushers to arrive this weekend? Par-tay.

Puerto Vallerta?

Or all the buzz on the aforementioned flyertalk.com is that Alaska will in inaugurating Hawaii service sometime later this year. Triangle trip - Chicago > Anchorage > Hawaii > Seattle > Chicago? Ooh.

I'd go to places like Adak or Dutch Harbor. Expensive to go otherwise, and you probably won't go there EVER on your own dime.

Dutch is very interesting; Adak less so. If you decide to travel out the Chain, be aware that flight delays/cancellations are not uncommon given the locally lousy weather. "Where the storms are born" - no lie.

BTW, "Dutch Harbor" is the Anglo name for the airport. Unalaska is the proper name of the city.

Alaska flies to Florida - it will be 82 down here today. Do you hear South Beach calling? ;-)

Go international. Ask if you can fly their partner NW Airlines to Amsterdam. Otherwise, if it's just use on Alaska Air, they now fly to Miami and Boston I think. But your best bet is Mexico. They go to many cities, so it depends on what you want to do.

another vote for Cancun!