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Chicago To Honolulu Round Trip
Almost everyone wants to go to Hawaii, but too many travelers think it’s too expensive to get there. We are here to prove you wrong.
United Cheap Flights To Chicago From $ 119
Cheap flights to Hawaii are back in a big way in 2023. Trust us: We’ve received and posted several Thrifty Traveler Premium alerts over the past few weeks, including…
Cheap flights and great deals to Hawaii just keep coming, and they couldn’t come at a better time. After Maui’s summer wildfires, state and local officials have been urging visitors to return to the island. That means Hawaii is open, no matter which island you want to go to.
With that in mind, you should put a trip to Hawaii back on your list for 2023 or 2024. So what else are we looking at, event-wise? We’re so glad you asked.
Finding a cheap flight to Hawaii is never a sure thing. Paying $600 to over $1,000 or more per ticket can be common, and travelers can go months without seeing even a half-decent deal on the islands.
American Offering Round Trip Flights To Hawaii From Multiple Us Cities Starting At $296
But that has changed dramatically: Flight deals and fare wars between airlines to Hawaii are hot and frequent these days. In the past few weeks alone, we’ve found and sent Thrifty Traveler Premium members several deals on flights from airports around the country for under $500 round-trip or less for travel in 2023 or 2024.
Exhibit A: This nationwide flight offer to all four of Hawaii’s big islands through winter and into spring 2024.
We’ve seen direct flights to Honolulu (HNL), Maui (OGG), Kauai (LIH), and The Big Island (KOA) across the country for half the departures or more. Now all you have to do is choose the best island to visit in Hawaii for your cheap trip.
If you live on the West Coast, you’re in for better fare. In fact, prices have fallen to record lows recently. Flights to Hawaii don’t get much cheaper than this.
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Flights under $200 from the mainland are already a great deal, but if you can get to Hawaii and back for that price, you’d better grab a chance!
Along with cheap flights, we’ve been finding award deals exclusive to these islands and alerting our Thrifty Traveler Premium members instantly. Yes, our premium members get award alerts to use their points and miles on all the cheapest cash fares, too.
We’re always on the lookout for Delta SkyMiles sales, deeply discounted offers to get a flight for a fraction of what the airline would normally charge. After a long absence, they have recently returned. And the deals don’t get much better than just 13,000 SkyMiles for round-trip flights to Hawaii!
Still, SkyMiles award rates are often astronomical. Lucky for you, there’s a great way to score a Delta flight to the islands for less: Using Virgin Atlantic Flying Club points instead.
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That’s right: Transfer your credit card points to Virgin Atlantic, keep the same bonus transfer time from banks like Chase, and you can book unlimited Delta flights for up to 35,000 points round trip! We’re not exaggerating when we say that these flights are usually over $1,000 in cash or about 100,000 Delta SkyMiles each.
If you have some points lined up anywhere, there’s probably a nice and easy way for you to fly to paradise this year. Be prepared to jump on fares like these when Delta drops rates.
Airlines are slashing prices for flights to Hawaii for 2023 and beyond, even as the Maui government asks for the return of travelers following wildfires on part of the island.

So feel free to book one of these Thrifty Traveler Premium flight deals. It’s the difference between paying $800-plus for your next trip to Hawaii … or less than half that.
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The disaster caused a flood of cheap flights to Hawaii, but many of them are stuck. This guide covers recent contracts.
But when it comes to finding cheap flights, it won’t always be this easy. While you may find that airlines are cutting prices right now, there are some general tips and tricks to keep in mind when it comes time to book the cheapest flights to Hawaii down the line.
Even West Maui areas including Kā‘anapali, Nāpili, Honokōwai and Kapalua, are expected to reopen on October 8, according to the latest emergency declaration signed by Hawaii Governor Josh Green. Some Hawaiians are asking travelers to avoid these areas of West Maui. However, there are many other places on the big island to visit responsibly.
Travelers are encouraged to plan or keep their existing travel plans to Maui while also being cautious and respectful as the community recovers from the wildfires.
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We will update this post with new deals and updates on cheap flights to Hawaii. It’s a hot spot for travelers, and we’re always on the hunt.
But if you want to stay up-to-date on deals on flights to Hawaii and other bucket list destinations as they happen, we highly recommend signing up for Thrifty Traveler Premium+! Premium+ members get access to all the best deals on flights to Hawaii – you’ll only see a small portion of them here and on other airline deals.
Looking for the best airline to fly to Hawaii on a budget? We regularly see cheap and direct flights to Hawaii on Hawaiian Airlines, Alaska Airlines, Delta Air Lines, American Airlines, Southwest Airlines, United Airlines, and WestJet – if you live in Canada, of course.
We always recommend booking your flights at least three to six months before you plan to travel – especially if your travel dates are subject to change.
Book Round Trip Flights To Hawaii Starting At $217
But as with all things in finding cheap flights, the key to getting the most bang for your buck on flights to Hawaii is simple: You may need to wait for a good price to come your way, then book on the cheapest date. Flexibility is the key to getting discounted tickets.
It depends: A good flight to Hawaii can happen at any time of the year.
But many find it cheaper to fly to Hawaii in January, February, April, and September through November. During the holidays and the peak travel months of June and December, you are more likely to experience higher prices, so it may be worth avoiding travel during those times.
If finding the cheapest flight to Hawaii is your ultimate goal, then you may not be too concerned about the best time to visit Hawaii – it is Hawaii, after all. However, if you’re evaluating options based on the cheapest flights to Hawaii you’ve found, here are some things to keep in mind:
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American Airlines is running a huge sale on flights to Hawaii through spring 2021, with fares as low as $197 round-trip from many major cities across the country. But you’ll want to book fast, as these prices only last until midnight on Friday, January 8!
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Would you like amazing flight deals like this delivered straight to your email inbox? We posted this Thrifty Traveler Premium offer first. Try it for just $5.99 a month!
Hawaii is already open to travel, with a requirement to provide a COVID-19 test taken no more than 72 hours before departure. And with this deal, you can get Honolulu (HNL), Maui (OGG), or the Big Island (KOA) for less from February to May. And American offers free changes and cancellations on these fares if you reconsider your trip.
You’ll find the lowest prices on direct flights from American Airlines hubs such as Charlotte (CLT), Chicago-O’Hare (ORD), Dallas-Fort Worth (DFW), Phoenix (PHX), or Los Angeles (LAX). There are also discounts from Las Vegas (LAS), Austin (AUS), New York-LaGuardia (LGA), and
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