Here’s a minor sale which offers a major discount. Visitors often tell me that there isn’t enough sale pricing from Chicago to Hawaii, so here it is.
The deal as of this moment:
- American Airlines
- Travel Dates: Mid August through early November.
- Best price varies from approximately $514 to $554 total.
- Availability: Quite limited, especially at lowest price, so act fast. Use flexible date search on Kayak, for example.
Steven (2 years ago)
Aloha,
This is a great deal and have been looking for a Chicago to Hawaii. However I am specifically looking for a CHI to OGG flight. Would you recommend taking a connector flight from HNL to OGG, or wait for a RT from CHI to OGG? I am flying early September and am aware that Fall deals have not yet all come out.
- Steven
Jeff (2 years ago)
Hi Steven,
OGG is running about $200 more those days, so at under $100 for RT between HNL and OGG, that would save you some money.
Chicago to Hawaii is one of the funnier markets. We see sales, but not as consistently as say New York, DC, or obviously the west coast.
If you’re really set on early September, I might just go for this deal. If on the other hand you’re more flexible, either look at early October, when there is a $590 fare to OGG, or perhaps wait.
Aloha, Jeff
Steven (2 years ago)
Great, thanks for the advice. Where do you recommend looking for getting the best RT deal from HNL to OGG.
Jeff (2 years ago)
That price I mentioned can be found on Kayak. I suggest using every tool out there, as no one tool ever has it all right.
Elise (2 years ago)
Hi!
That’s a great deal!
I am looking for a flight from San Diego for this summer (July 18th – 24th). Would you recommend wait or buy now?
Thank you,
Elise.
Jeff (2 years ago)
Hi Elise,
I’m afraid that at this point, the pricing is grim. Mid $500′s from LAX or mid $600′s from SAN. It isn’t likely to get better or worse. So I’d probably just keep watching. There’s a slim chance we’ll see another round of summer reductions.
Aloha, Jeff
Mark (2 years ago)
Jeff,
Do you think I should book this multi-city originating in Chicago?
$695 per person – US Airways
Depart: September 15th ORD 7:20a – OGG 2:13p (11h 53m) 1 stop
Return: September 28th LIH 9:04p – ORD 2:14p (12h 10m) 2 stops
Seems not half bad. I posted on another thread this week and prices at that time were closer to $900.
Thank you!
Jeff (2 years ago)
Hey Mark,
Not bad, not great, in my opinion. A somewhat better connection is available on AA at about the same price.
It just comes down to how badly you need to book this now. I’d wait, but that’s me. The more I do this, the more I don’t want to pay extra if its avoidable. On the other hand, sometimes you just have to book now, for sanity sake. When I do that, I try to never look back.
Aloha, Jeff
Kris (2 years ago)
I’m with Steven, looking for September fares to OGG. The general tone of the post rings true, that us here in Chicago seem to be left out of some of the big headline sales that you see on most travel sites and blogs.
For me, the September timeframe is for the Maui Photo Festival and Workshops at the Hyatt, so there’s only a little wiggle room date wise.
Still, a November trip always sounds good, too.