Chicago to Hawaii Including 2009 Peak Seasons $400
Dec 03, 2008
8 Comments
Updated 2/1/09: This on and off fare fare is gone for now.
Updated 1/25/09: The fare is now $473 RT (all-inclusive) to Honolulu or $493 to Maui. Availability is through March 4, although I suspect it may be extended until April 30.
Updated 12/31/08: Fare is gone for now.
Updated 12/25/08: AA has dropped the price to $343 RT!
We are starting to see the New Year deals really strike now.
This excellent offer includes most all the players and is valid during Spring Break and throughout the peak summer season as well. For the best choice of those dates, act quickly.
- Cost: $400-$408 RT (all-inclusive)
- Airlines: American, Delta/Northwest, United
- Dates: Travel through October 2009
- Minimum/maximum days: 3/60
- Advance purchase: 7 days
- Availability: Excellent
First To Report the Web's Best Hawaii Deals Plus Industry News and More. We Are All Travel, No Ads, Hawaii Based. 
I am looking to book a Chicago to Maui trip for early/mid September 2009. Do you have any tips or recommendations in searching for the best deals? Typically, when do you see September fares being offered or going on sale?
Thank you -
Hi Steven,
Typically we expect to see the Fall deals (with validity starting the 2nd half of August) start appearing 4-6 weeks prior.
As I recall last summer, however, the airlines dragged their feet and didn’t really roll the Fall deals out until quite late, like late August.
Hope that helps.
Jeff
We are looking to plan a trip to Hawaii mid June or end of June/beg of July. We’re hoping to go to Maui and Kauai, but are flexible. Any suggestions on when to book or where to look for airfare deals?
Thanks,
Cathy
Hi Cathy,
Your planned trip is obviously in high season. At present the best price is $620, which isn’t bad at all for that time of year.
The difference between the best deal we’ve seen ($400) and the current $620 offer isn’t that great. So if it were me, and I had my heart set on a summer vacation in Hawaii, I’d buy it now. You never know, the prices could easily inch higher.
If you are more flexible of course, wait, and better deals may arise at any time. On the other hand, they may not.
I hope that helps.
Aloha,
Jeff
Looks like I might have missed the goodness. We’re planning a trip to Hawaii (from Chicago) Aug 8 – 17. Ideally AA since I have some miles but all can find are 800+ airfares. Could they go higher still or should I hold out for a lower fluctuation?
Thanks!
Hi Kevin,
Yes this deal has been gone for a while now. I wish a had a simple answer to your question, but I don’t. So if it were me, and I only had those dates available and my heart set on Maui, then I think I’d go ahead and book now. On the other hand, your dates are at the end of the peak season, and it wouldn’t surprise me to see a deal that would be a lot sweeter than the over $800 current price.
One other thought. You can get from SFO to OGG for about $450, and from ORD to SFO for under $200. I don’t know if that is desirable, but wanted to mention it.
Aloha,
Jeff
Hi Jeff,
I am planning a wedding in Maui in late October and we are trying to help our people find the best fares. Currently we can get there for 435 from LA which seems really good, but prices for SAT or AUS where a lot of our people are coming from are 700+. Do you think we should advise people to wait until the fall deals start to come up, or should we suggest they buy now?
Thanks
Aaron
Hi Aaron.
Congratulations.
October will unquestionably be a cheap time to come to Hawaii. I know that waiting will be completely nerve wracking, but you will definitely save oodles of money if you wait on the airfare until about August. Whenever the Fall deals show up, we’ll definitely be posting them.
I hope that helps.
Aloha,
Jeff