Unbelievable Deal Alert: Chicago to Maui (or Maui to Chicago!) for Under $400!

Hello travel enthusiasts! Get ready to have your wanderlust ignited because I’ve just stumbled upon an absolute steal of a deal that I simply had to share with you all. As you know, I spend countless hours scouring the web for the best travel deals so you don’t have to, and this one is truly exceptional. Right now, Alaska Airlines is offering round-trip basic economy flights between Chicago (ORD) and Maui (OGG) – or vice versa – for an astounding $384! Yes, you read that correctly: under four hundred dollars to paradise.

This isn’t some fly-by-night, gone-in-a-flash deal either. This incredible pricing appears to be available for travel between January and March 2026. While that may seem like a long way off, planning ahead is the key to securing these kinds of incredible offers. And trust me, for this price, I’m already considering booking myself a trip.

Digging into the Deal: What You Need to Know

Now, before you rush off to book (which, honestly, I wouldn’t blame you for!), let’s break down the details and discuss what you need to know about this specific fare. Firstly, it is essential to acknowledge that this is a basic economy fare. This means you’ll encounter some restrictions compared to a standard economy ticket. These restrictions can vary slightly from airline to airline.

With Alaska Airlines’ basic economy (Saver Fare), be mindful of the following:

* Seat Assignment: You won’t be able to select your seat for free during booking. Alaska Airlines assigns seats to Saver Fare passengers at check-in, which can happen within 24 hours before your flight. If you want to guarantee a seat next to your travel companions, you would need to pay extra to select your seats ahead of time or upgrade to a Main Cabin fare. * Changes and Cancellations: Saver fares are generally non-refundable and non-changeable. Be extremely certain of your travel dates before booking, as you likely won’t be able to alter them without forfeiting the ticket entirely. * Baggage Allowance: The basic economy fare includes one personal item that fits under the seat in front of you. If you want to bring a carry-on bag that fits in the overhead bin, you will have to pay extra for it. Checked baggage also incurs a fee.

For those who prioritize flexibility and comfort, the main cabin fare may be more suitable. However, if you’re comfortable traveling light and are confident in your travel dates, this basic economy fare is an unbeatable way to get to Hawaii.

Why This Deal is So Exceptional

Let’s put this price into perspective. Round-trip flights from Chicago to Maui typically cost upwards of $800, and often much more, especially during peak season. Even finding a deal in the $600-$700 range is considered a win. Securing a flight for under $400 is simply phenomenal.

This is particularly appealing because Hawaii is often perceived as an expensive destination. While accommodation and activities can add up, this drastically reduced airfare significantly lowers the overall cost of your trip, making a Hawaiian vacation much more accessible.

Additionally, the January-March timeframe is excellent for visiting Maui. The weather is typically pleasant, with warm days and comfortable evenings. While it is technically considered the rainy season, the showers are usually brief and localized, leaving plenty of sunshine for enjoying the beaches, hiking, and exploring.

How to Find and Book This Deal

The best way to find this deal is by using Google Flights or directly through the Alaska Airlines website. When searching, be sure to select “round trip” and specify your origin and destination airports (ORD and OGG, or vice versa). Experiment with different dates within the January-March 2026 timeframe to find the lowest fares. I have found that Tuesdays and Wednesdays often offer the best prices, but it is worth checking other days as well.

Once you’ve found a date that works for you, click through to the Alaska Airlines website to complete your booking. Be sure to carefully review the terms and conditions of the basic economy fare before finalizing your purchase.

Maximize Your Savings with the Right Credit Card

Okay, you’ve found the deal, and you’re ready to book. Now, let’s talk about how to maximize your savings and earn rewards by using the right credit card. As a frequent traveler, I always advocate for using a travel rewards credit card for all your travel purchases, and this is no exception.

Here are a few of my favorite credit card strategies to consider for this booking:

* The Alaska Airlines Visa Signature Card: If you are a loyal Alaska Airlines flyer, this card is a no-brainer. You’ll earn miles on your purchase that you can redeem for future Alaska Airlines flights. The welcome bonus is also frequently quite generous. Furthermore, you get a free checked bag for yourself and up to six other passengers on the same reservation, which can offset the baggage fees associated with a basic economy ticket. I love this card because Alaska miles are some of the most valuable in the industry, and I have used them to book many incredible trips over the years. * A General Travel Rewards Credit Card: If you’re not particularly loyal to Alaska Airlines, a general travel rewards card is still an excellent option. These cards typically earn points or miles that you can redeem for a variety of travel expenses, including flights, hotels, and rental cars. I find these cards provide the most flexibility since you are not tied down to one airline. * A Credit Card with a Travel Portal Bonus: Some credit cards offer bonus points or miles when you book travel through their specific travel portal. Check your card’s benefits to see if this applies to you. However, I advise comparing the prices on the portal with the Alaska Airlines website to ensure you’re still getting the best deal. * Don’t Forget the Sign-Up Bonus: If you don’t already have a travel rewards credit card, now might be the perfect time to apply for one. Many cards offer lucrative sign-up bonuses after you meet a certain spending requirement within a few months of opening the account. This can significantly boost your travel rewards balance.

Pro-Tips for Planning Your Maui Getaway

Now that you’ve secured your flights, let’s talk about planning the rest of your Maui vacation. Here are a few of my favorite tips for making the most of your trip:

* Consider Alternative Airports: While the deal focuses on flights to and from Chicago, also check fares from nearby airports if you are able to drive. Sometimes flying from a smaller airport can save you money. * Book Accommodation in Advance: Maui is a popular destination, especially during peak season. Book your accommodation well in advance to secure the best rates and availability. Consider renting a condo or vacation home for a more spacious and budget-friendly option. * Rent a Car: While Maui has some public transportation, renting a car is the best way to explore the island at your own pace. Be sure to book your rental car in advance, especially if you’re traveling during peak season. * Explore Beyond the Beaches: While Maui’s beaches are stunning, don’t miss out on other attractions, such as the Road to Hana, Haleakala National Park, and Iao Valley State Monument. * Take Advantage of Free Activities: There are plenty of free activities to enjoy on Maui, such as hiking, swimming, snorkeling, and exploring the local towns. Pack a picnic lunch to save money on dining out. * Embrace the Aloha Spirit: The people of Maui are known for their warmth and hospitality. Take the time to learn about the local culture and embrace the “aloha spirit.”

Don’t Miss Out!

This deal is simply too good to pass up. A round-trip flight to Maui for under $400 is an incredible opportunity to experience paradise without breaking the bank. So, don’t hesitate! Head over to Google Flights or the Alaska Airlines website and book your tickets today. I wouldn’t be surprised if these fares disappear quickly.

Happy travels, and I hope to see you on the beaches of Maui!