Cheap Flights from Chicago (MDW) to Kailua-Kona (KOA)

Popular airlines from Chicago Midway Airport (MDW) to Kona Intl. Airport (KOA)

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Flights from Chicago (MDW) to Kailua-Kona (KOA)
Origin airport
Midway Intl.
Destination airport
Kona Intl.
Distance
6745 km

Chicago to Kailua-Kona Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Kailua-Kona offer the perfect respite. Not only does exploring Kailua-Kona provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Kailua-Kona may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from to today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Kailua-Kona are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Kailua-Kona more flexibly many prefer to purchase one-way tickets with options to take different airlines. A one way ticket to Kailua-Kona is now!

Frequently asked questions

Is it cheaper to buy a plane ticket from Chicago Airport to Ellison Onizuka Kona Intl. Airport at Keāhole last minute?
Booking your flight from Chicago Airport to Kona Intl. Airport (KOA) last minute could save you a nice sum if you luck out and find a bargain. However, tickets usually don't come down in price as the date of departure nears. If you wait around, flights could also be booked up or the best seats gone (hello, middle seat!). If you'd rather not take any chances, book well ahead of when you want to leave. Remember that some of the most awesome deals can be found up to 12 months in advance. If your favorite carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia constantly.
What airports do you fly into for Kailua-Kona from Chicago?
From Chicago, you can reach Kailua-Kona through Kona Intl. Airport (KOA), Waimea-Kohala Airport (MUE) and Upolu Point, HI (UPP-Upolu). Research which hub is the best option for you before you make a decision. If you decide on Kona Intl. Airport (KOA), it's about 11 kilometers northwest of the center of the city. Use the dollars you save when booking your ticket with Expedia to check out the city's popular attractions, such as Kailua Pier and Kona Brewing Company.
Can I change the date of my flight from Chicago Airport to KOA?
Quickly make changes to your MDW to Kona Intl. Airport (KOA) ticket via the Expedia Trips portal. But before you make any amendments, check the rules and restrictions in your itinerary to see what the carrier will let you do and if change fees apply. Some airlines have a change fee per person, plus any difference in fare prices. But if you booked in the last 24 hours, you may be able to cancel for free and book new flights. You can also visit our Customer Service portal for more advice and to chat with our Virtual Agent.