Hello from Bettendorf, we booked out tickets for trip in Feb, after watching prices for several weeks. Out of O'Hare we are at $345.00 RT. We still need to book tickets for our kids and g'kids, who are joining us for a week in March, we are hoping to use our miles from 2 credit cards for their tickets. Last year, using our FF miles, the "price" in one day, went from 80,000 to 40,000 so it pays to check often. A friend puts his ticket on his credit card then uses the miles to upgrade. Peter Greenberg said the best prices are after midnight on Tues. but I can never stay up that late ! Go Hawkeyes!!!

It's not to early to start checking airfare. We normally go to STT in late October early November and will start checking as early as January, it seems I've always been able to find good prices 8-9 months out. American/US Air & Spirit usually have the best fares out of ORD, with American having the most over the past few years. Good luck in your search.

PS: Over the last 4-5 years we've been paying in the low to mid $300's /pp with all taxes and fee's (not including any baggage rip off fee's)

We are going early January 2011 and have been watching airfare out of ORD for two months. It was as low as $303 in July, and is currently $387....should have booked it in July. I don't think it ever gets below $300. I agree, Tuesdays seem to be when fares drop.

I saw 2 tickets come up for $240 RT from Ohare and grabbed them. With insurance, $266 each. Hawaii kept going up in price and I couldn't pass up this price.

austinill...what site did you use to monitor rates and buy at $266 each? I believe the lowest price we ever got was about $225 our of ORD in 2005 or 2006. I'd like to use your site if it works well for monitoring. I often use Yapta and Orbitz, but wonder if there's a better place for IA Joe to land his "best case scenario"?

We are flying out of Chicago in early November 2010 with a price from AA at $315.70 pp/rt and that includes taxe (fare: $525.00 plus $63.70/tax). That was a great price, since we had a price of $385.00 on hold. My wife was just about ready to purchase the higher price, when the $315.70 came up on the AA website. We always fine the best price directly on the AA website. Add that we got a fantastic rate at the Grande Bay/Cruz Bay, we are really excited about the cost of the airfare/lodging on this trip. Our trip this past May, was somewhat higher in cost and we stayed at the Wyndhum on STT ($110.00/night).
There were times when we were able to fly out of our airport here in Iowa and the airfare would be cheaper to STT, then starting in Chicago. Those days a gone I guess, because the last 4 times to the island, we have had to start our trip in Chicago, Anyway, the drive to O'Hare isn't that bad for us.
Hope this helps and look forward to hearing about your trip.

I used expedia. Have always had good luck. Timing is the key. In '05, was looking for tickets to Oahu. Started at $900, saw them drop to $700 and was ready to book when next morning they dropped to $500. For 5 tickets, I save $2,000 rt by waiting a few days. VERY LUCKY.

This one just popped up. Saw RT to Oahu for $461, but they were gone before I could do anything.

Has anyone checked flying out of Midway on Delta? The last 2 yrs we have flown with Delta for 350 pp/rt in Aug. We live in IN and it is so much easier driving to Midway then O'Hara. We use to fly on AA out of O'Hara and had to take a bus from IN but when flying out of Midway we just drive to the airport and park there---so easy and less time. We were so impressed with Delta.