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Help me plan our first vacation!
H and I want to go on a spring break trip. We were thinking April 6-11 (Good Friday- Weds). 5 nights.
We
want to go someplace very warm where we are guaranteed to have great
weather (no rain, no hurricanes), on a beach, preferably all-inclusive
so that we can drink as much as we want. 
Is it possible to find this for less than $1,000? This is our max budget, including airfare, flying out of Chicago.
Has anyone done this for less than $1,000? Tell me your secrets!
Re: Help me plan our first vacation!
I don't have any great secrets
BUT I believe this is very possible to do if you start looking now- and book now- and wouldn't mind going to Mexico. The beach cities of Mexico are very safe and tourist friendly, and they have some great AI's. I know $1000 is your budget, however I am almost positive this is do-able for the $1200 or less range, if not your current budget anyway.
Check priceline... I always start my searches through them and build from there. Good luck!
There are some things listed on cheap caribbean that are like $479 pp including flights for three nights. In the Bahamas.
That's the cheapest I can imagine, and it's a) not the right amount of time and b) flights from ORD may be more expensive as I'm not sure you can fly direct to Nassau.
Also, the dates she wants are probably blacked out since it's easter/spring break.
I think it's really unlikely. I'd cut back the number of nights or maybe go on a cheap 3 day cruise.