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Airfare for 6

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You tried flying on a tue, wed or sat? 250/ea aint too bad... depends where you go in FL but from NYC you can generally go for $200/rt.

With 6 peeps driving might be an option. @ 25mpg Chicago to Orlando is approx 1100mi. 2200/25 = 88 gallons of gas @ $3.5/gal = total cost of $308. I'd drive.
 
Well if you gotta fly that's the cost of convenience. Fwiw I think that's an ok price. You could maybe generate some miles, maybe sign everyone up for a new account... I think my parents did that one year and we all got a leg.free or something. If you're confident in the carrier you'll be flying go to giftcardgranny.com and save 0-5% buying gift cards ahead of your purchase.