Cheap O Air - I just checked out round trip tickets in July from Seattle to Rome & found tickets for $1,100 (with one stop) OR JFK to Rome in April for $420 bucks nonstop - now we are talking! Plus with their Presidents Day Sale take $10-$15 off the final price (ending 28/02/09)
Lufthansa is offering numerous discounted flights including Bella Italia with tickets to Italy from $180 for the spring and they just released a Romantic Europe Sale including a Buy-1-Get-1 at 50% OFF special to some of Europe's most popular destinations. Fly to Rome or Venice starting at $546 - but remember, that's each way for 2 people. So it's actually $273 each way per person after the discount! Depart April 3 through May 22 to take advantage of this special. Just be sure to book soon as we don't expect this offer to last long.Travel Zoo - is packed with deals take a look - that's where I found the Lufthansa sale!
Kayak - I randomly checked a week in June & found JFK to Bologna for 805 Euro.
Skyscanner is great too & checks for inter-European flights which come in handy when you are hitting up multiple destinations or find an outrageous deal to London & then need to find your way from London to Italy for example. Also it uses a handy graph of each month, with the cost per day of flights so you can see when its cheapest to fly.
How far of a drive are we from the airport?
Rimini - 1.5 hours
Ancona - 1.5 hours
Forli - 1.5 hours
Bologna - 2 hours
Florence - a little over 2 hours
Rome - a little over 3 hours
Venice - 4 hours
Milan - 5 hours