Best Website to help us find the following info for travel plans. . .any destination ideas too?

Question

Here is my situation:
1. I can fly from Moline Quad City Intl Airport (MLI) or from Chicago, IL, - O'Hare (ORD)
2. My travel companion can fly from New York ISP (Islip, Long Island) or from LGA (LaGuardia) in the city.
3. We can fly Fri evening 08-04 through Tues evening 08-08, but we both prefer to fly Fri evening 08-11 through Tues evening 08-15
4.We are trying to find a destination city to fly to so we can spend some time together and will need one hotel room and probably a rental car or be able to walk or use city transit.
5. We have spent hours and days and weeks searching sites and are frustrated. How can we coordintate this to find flights for under $300 round trip a piece?
6. One of us prefers not to go anywhere hot. We both like the idea of Canada. We both want to get away from Chicago and New York.

ANY tips or pointers????? Is complicated, escpecially since we don't know where we want to meet at. Any help is appreciated . . .no 'smart remarks' please. THX!!!

Just to clarify we mean $300 each for the round trip tickets. . . not including hotel and car and stuff.

Answer 1

Try this site. You can search prices on motels,car rentals,air travel etc... Hope this helps you, and have a good trip.

Answer 2

For $300 a piece - thats gonna be hard if not impossible to find. You might try Southwest airlines, as they are having a lot of specials on one way tickets (With a 21 day advance purchase).

Answer 3

Try Spirit airlines they also are having tons of deals right now

Answer 4

You can meet in Toronto (YYZ). You will not have to rent a car.

Air Canada: http://www.aircanada.com/

Toronto is wonderful (I'm prejudiced!):
http://thetravelzine-torontosc.spaces.msn.com/