Southwest® flights from Chicago (Midway) to Kona (Island of Hawaii) from $297

What to expect at Kona International Airport (KOA)

Ellison Onizuka Kona International Airport (KOA) is a smaller airport that primarily serves leisure travelers. It’s a perfect access point for the western half of the Big Island, including the Kailua-Kona area and the Kohala Coast resorts.

Like several other airports in the Hawaiian Islands, KOA is a partially open-air facility. You’ll feel the island breeze throughout the open-air terminals, and passengers exit the plane straight onto the tarmac. While the tropical climate is typically comfortable for travelers, it’s a good idea to dress in layers so you can adjust to the temperature at your own leisure.

Island hopping from Kona (KOA)

There’s more than enough on the Big Island of Hawaii to keep you occupied after your flight from Chicago to Kona, but it's also a convenient connection point if you want to explore more of Hawaii. Flying is the most efficient way to get between islands, and frequent flights connect the Big Island to Oahu, Maui, and Kauai.

Whether you're planning a multi-island itinerary from the start or just feeling spontaneous once you land, it's easy to build in a quick island hop. Check out Hawaii inter-island flights and explore all Southwest flights to Hawaii to see what works for your schedule.

Getting from KOA to Kona and nearby areas

After your flight from Chicago to Kailua-Kona, you’ll be just 15 minutes by car from the downtown area and from numerous resorts. However, note that the Big Island is indeed pretty big, and that it takes a little more planning to get around. The most common transportation options include:

• Rental cars: Most visitors to the Big Island choose to rent a car. It’s the most convenient way to get around if you want to venture beyond the immediate Kona area. For the smoothest experience, book your car in advance, then pick it up at the airport lot.
• Rideshares and taxis: Finding a rideshare or taxi is usually easy at KOA, but note that availability might be limited at night or in rural areas.
• Hotel shuttles: Resorts in Hawaii often include an airport shuttle service for guests, but contact your hotel ahead of time to learn about times and availability.

How to find cheap flights from Midway (MDW) to Kona (KOA)

Searching for cheap flights from Midway to Kona? These tips can help you find the best deals on airfare from Chicago to Hawaii:

• Use the Low Fare Calendar: The Southwest Low Fare Calendar lets you instantly compare travel dates and find the cheapest days to travel.
• Book early: You’re not the only traveler dreaming of an island vacation, so book your airfare from Chicago to Hawaii sooner rather than later.
• Travel in shoulder seasons: The farther you get from the peak periods in the summer and the winter holidays, the more likely you are to find a great deal on fares.
• Get alerts: Sign up for Southwest email alerts, so you always have the inside scoop on new promotions and flight deals.

What’s the best time to travel from Chicago to Kona?

• Peak travel periods: Winter holidays and school breaks are some of the busiest times to visit the Big Island. If you're planning your Hawaiian vacation during these popular travel windows, book flights, accommodations, and rental cars well in advance.
• Whale watching: Humpback whales migrate through Hawaiian waters between December and March, making this one of the best times to experience whale-watching tours from the Big Island.
• Best value: If your travel dates are flexible, visiting outside major holidays and peak vacation periods can often mean lower fares, greater hotel availability, and a more relaxed experience across the island.
• Ocean conditions: The Kona Coast offers excellent snorkeling and other water activities year-round, but ocean conditions change with the seasons. Summer generally brings calmer waters, while winter can produce larger swells around the island's northern shores.

What to do in Kona after you land

• Fresh Kona coffee: Tour coffee farms and drink the island’s legendary coffee straight from its source.
• Snorkeling at Kealakekua Bay: Visit this stunning coral reef, packed with colorful fish and corals in clear, calm water.
• Hawaii Volcanoes National Park: Take a day trip out to this unique national park and see landscapes you won’t believe are real.
• Manta ray night dives: Meet these majestic creatures on their home turf in an unforgettable nocturnal experience.