Your Family Guide to Visiting Hawaii on a Budget

With gorgeous beaches, wonderful weather and rich cultural experiences, Hawaii is a remarkable destination for a family vacation. If you think that a trip to our 50th state is out of your budget, think again. Here are some tips to help make it possible for Chicago families to say “Aloha!” to paradise.

Southwest now flies to Hawaii.

Southwest Airlines recently began operating flights to airports throughout the Hawaiian islands, including Honolulu on Oahu, Kahului on Maui and Kona on the island of Hawaii. Southwest is known for its low fares and that combined with using its Rapid Rewards frequent flier program can make travel more affordable for families. It’s the only way my family could afford to get to Hawaii last month.

Flights from Midway typically go through Oakland. It’s a nice chance to stretch your legs and let little ones burn off some energy before continuing on to paradise. 

Avoid additional fees where you’re staying.

While a hotel may seem like the obvious choice for lodging, beware the extra costs that may not be so apparent. Many hotels charge a resort fee, often around $35 per day, and it is not unusual for them to also charge a parking fee of between $25 and $40 per day. Those two costs add up quickly. They can be buried in the fine print and while easy to miss at the start, you’ll definitely notice on your bill. Be sure to ask before booking. 

Consider other options that don’t have those charges, such as a vacation rental of either a condo or a home. For example, the Kaanapali Alii is a resort where you can book condos without resort or parking fees, and offer other ways to save on food. (See below.) It can also be a great option if you want to have a little space to enjoy after the kids are tucked in bed for a nap or bedtime. Should you need at least a little hotel time to really feel like you’ve gotten away, consider splitting up your stay between traditional hotels and rental options.

Save on food.

Eating in restaurants for every meal gets expensive, and that’s especially true in Hawaii. The good news is that there are more cost-effective dining options. Consider buying food there. Pack a reusable bag or two, as they charge for them. If you’re traveling with a decent number of people, bring your Costco card, and you’ll find Costcos on Oahu, Maui and Hawaii. 

While cereal or bagels for breakfast can be a help, also consider making your dinners, too. Check and see if where you’re staying has grills. At the Kaanapali Alii, they have a Grill Master who will help you cook up a delicious dinner by assisting with operating the grill, offering expert tips and even sharing some delicious rubs. The kids can play in the pool nearby and don’t even have to get dressed. There are also food trucks all over and they are downright delicious, as well as easier on the wallet than a sit-down restaurant and tons of fun.

Take advantage of free activities.

When we were in Hawaii, I asked my daughter about doing a variety of activities, which would have cost a fair amount of money. To my surprise, she said, “There’s a beach, right? And a path we can walk along to other beaches? And a pool? That’s enough!” She was content with what was available to us without additional cost. While there are a lot of amazing sights to see in Hawaii, and they are worth seeing, have a conversation with your family to make sure that you’re all on board about wanting to go before you pay a lot of money. 

Also, inquire as to what activities are available where you are staying. Many resorts and hotels offer free activities. (If you are staying at a hotel with a resort fee, find out what’s included and take full advantage!) The Wailea Beach Resort has a game room with arcade games, board games, shuffleboard and more — the perfect option for a break from the sun. For example, at the Kaanapali Alii, kids can take ukulele lessons or join in a tennis clinic. Head to Black Rock Beach to see a torch lighting and cliff diving ceremony. It’s put on by the Sheraton Maui Resort but free for anyone to watch from the beach. 

You can also find free activities in other locations. On Maui, the Shops at Wailea host weekly free concerts, and Whalers Village hosts free hula shows and lei making classes. Activities in nature can be economical, too. Many state parks are free and on Oahu, admission to the stunning Diamond Head State Monument is $5 per car, $1 per person for pedestrians. 

Consider if a car is really necessary.

Renting a car in Hawaii may not be entirely necessary, depending on where you’re staying and what you want to do. Uber is readily available. We crunched the numbers on getting an Uber to and from the airport, and from one hotel to another. It was much cheaper than renting a car, and that’s before you consider the parking fees. 


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