You might consider taking a bus trip to a casino in Indiana. They give you great rates on the hotel because they want you to gamble. It not warm but the have indoor pools. The also offer tours to other casinos like Las Vegas and even Louisiana. Just check web sites. Flying cost entirely too much. SOmeone told me how much there plane ticket it was twice as much as last year. A organized bus trip might be your best bet.
I m thinking of Las Vegas for your trip because you can always get great deals on hotels, food, and more in Las Vegas. Also, there are so many inexpensive and free attractions in Las Vegas which will help save you money. Skip all the gambling and you ll have it made. Las Vegas is fun for people of all ages. Check out Southwest flights and see what deals you can get. I fly Southwest out of Midway Airport and they always have some good deals depending on when you re flying to Vegas.Here is a link with more information on Las Vegas:http://www.lasvegas.com/attractionsHave fun!
Checkout travelbyjen.com. They mostly have Caribbean vacations so you would need a passport, but they also have packages for florida and Hawaii. I saw a flight for you from IND to Cancun for $478 all inclusive, but you would have to leave buy the 16th.
There is a great website called www.allegiantair.com. They have great affordable vacation packages. My Husband, My Son and I would fly from Vegas to Idaho round trip and stay in a hotel for a week, all under $500.00. Check it out, it s worth it.
Try http://www.kayak.com/buzz or http://www.travelzoo.comAirline tickets go up the closer you get to the date of travel, and especially once you get within 2 weeks, so honestly I doubt you ll find exactly what you re looking for at this point. You could probably do the same trip for cheaper if you can do it in January or February (or if you had booked it earlier).