Flying to the Hawaiian islands from the mainland can seem like a daunting haul, especially if you don’t happen to live along the west coast. For us, living in Chicago, and for anyone else travelling from our area or along the east coast, you’re in for some serious seat time on an airplane, with total transit times starting at about 9 hours for a direct flight.
So, do you try and bite the bullet and do the 9 hours all at once, or is it better to add a connection and time to stretch your legs halfway through? Good question.
In the Past
In planning our previous trips to Maui, we have always chosen a direct flight to Kahului. Since we’re in Chicago, we have more than a decent selection of flight options flying out of O’Hare, and I realize for those not living near a major airport, direct flights aren’t an option anyway.
The thought behind taking a direct flight, at least for me, was wanting to get to Maui as soon as humanly possible. There are a few other factors that have worked their way into that line of thinking as well. When we went to Oahu for our honeymoon, we flew NWA, which had to connect to their central hub in St. Paul, MN. Somewhere between Chicago, St. Paul, and Honolulu, Cindy’s luggage chose a different route and didn’t show up 3 days later!
Two years after that, for our first trip to Maui, we decided to book a direct flight with United instead. We thought we were a little safer that time, but wouldn’t you know it, 2 months before our trip, the travel agent calls to tell us that United added a connection to the existing flight we had already booked. And, of course, we sat on the plane, stuck in the gate, for a good 45 minutes with a mechanical delay, and almost missed our connection. Running through airport terminals with your carry-on luggage is not really the way to start a relaxing vacation in paradise.
This Trip
But as we’ve come to realize after flying direct these past few years, that direct flight (all 9 hours of it) can really take it’s toll. Crammed in that little seat, not being able to walk around as much as you’d like, and your iPod dying about halfway through can all add to the challenge of keeping your spirits up. So this time, we decided to ditch the direct flight and give the connecting route another chance. We will be stopping in San Francisco on the way to Kahului, which adds a few hours to the total transit time, but will hopefully be more comfortable.
We’ve changed our return flight for this trip, too. In the past, we’ve opted for the red-eye back out of Kahului, which would leave late Saturday night, connect in SFO early Sunday morning, and get us back to Chicago a little after Noon on Sunday. The two schools of thought there are that (1) you get to spend more time on Maui that Saturday, and (2) you can just take advantage of your normal sleep habits and get some shut eye on that first flight.
Of course, like anything else, there are pros and cons with that approach. I’ll get into more details another time, but this trip, we’ve chosen a 2pm flight out of Maui, which will arrive in SFO about 8:30pm. The flight to Chicago isn’t until 11:45pm, so hopefully that will give us time to grab something to eat, stretch out for awhile, and still sleep on the plane home. We’ll be arriving at O’Hare just before 6am, though, so even if a night’s rest on those oh-so-comfy airplane chairs isn’t satisfying, we can still sleep in our own beds when we get home early Sunday morning.
So, Which is Better?
It depends, really. Like everything, it’s a matter of preference and what your situation calls for. I have always liked the direct flight and the red-eye home, mostly because I just tough it up and adjust fairly well to all of those drawbacks. Cindy likes to move around more, and can’t always sleep on the plane when she wants to, so right there you have two different sets of preferences.
I do look forward to seeing how the change in our flying habits works out on this trip, and if it goes off without a hitch (knock on wood) and makes the overall travel more bearable, I’m open to switching for future trips. We’ll have to wait and see.
What’s Your Preference?
We’d love to hear your thoughts on this topic. Tell us about your travel experiences to any of the Hawaiian islands, and what preferences or tricks you have to make the time fly by (pardon the pun). And for you folks in California, try not to rub it in too much, okay? :)
Mahalo.




I’ll be interested in finding out how it works. I would imagine that it will be easier to get over jet lag.
You’re lucky that you have the ability to fly non-stop to Hawaii. We always have to connect through either Dallas or Chicago.
Yeah, I was thinking about folks on the East coast, too, when I writing this. We also met an older couple at O’Hare a few trips ago that was from Edwardsville, IL, which is down in Southern Illinois near St. Louis. They had to jump on a plane near them at some horribly early morning hour just to get to O’Hare for the connecting flight to SFO we were sharing. Yikes.
And then we met a family at a luau the following year that was from San Diego, and they had taken the red eye to Maui the night before and talked about the flight like it was no big deal. So jealous.