$216 Cheap Flights from Chicago (MDW) to Kailua-Kona (KOA)

Bundle Your Flight + Hotel & Save!

Featured airlines

Top nine airline logos for desktop

    Plan, book, fly with confidence
  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • one key icon
    Earn twice
    Earn your airline miles on top of our OneKeyCash

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

Prices were available within the past 7 days and start at $216 for one-way flights and $432 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Delta
Flights from Chicago (MDW) to Kailua-Kona (KOA)
Origin airport
Midway Intl.
Destination airport
Kona Intl.
Airlines serving
Delta
Roundtrip price
$431
Distance
4215 mi

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 $216 now!

Frequently asked questions

How much is a one-way flight from Midway Airport to Kona Intl. Airport (KOA)?
Get ready to score a terrific deal, because one-way Chicago flights to Kailua-Kona start from $516. This info is based on the cheapest fare found on Expedia for this route with a departure date within the next three months. This airfare is for an Delta flight, leaving from Midway Airport on June 11 2024 and landing at Ellison Onizuka Kona Intl. Airport at Keāhole. The price of this airfare was last updated on May 31 2024 and has not changed since.
Is it cheaper to buy a plane ticket from Chicago Airport to Ellison Onizuka Kona Intl. Airport at Keāhole last minute?
Booking your trip from MDW to Kona Intl. Airport (KOA) last minute could save you a pretty penny if you luck out and find an epic deal. However, fares don’t typically get cheaper as the date of departure nears. If you take a wait-and-see approach, flights could also be booked out or the best seats taken (because who wants the middle seat?). If you’d rather play it safe, book well in advance of your departure date. Don’t forget that some of the biggest bargains can be found up to 12 months in advance. If your preferred airline hasn’t released its fares yet, check back regularly as deals are updated on Expedia constantly.
What is the cheapest airline flying from MDW to KOA in the next 90 days?
The cheapest carrier flying from Chicago to Kailua-Kona found on Expedia is Delta, which has fares starting from $516. This price is based on fares found on Expedia with a departure date within the next 90 days. The flight jets off from MDW on June 11 2024 and arrives at Kona Intl. Airport (KOA). The pricing information was updated on May 31 2024 and has not changed since.
What's the cheapest price for a flight from Midway Intl. Airport (MDW) to KOA next month?
Lock in a flight from Chicago to Kailua-Kona for only $516. This is the cheapest price for this trip with a departure date in the next month. It’s an Delta flight heading off from Chicago Airport on June 11 2024 and landing at KOA. The pricing info was correct as of May 31 2024 and has not changed since. It was found after searching all available flights on Expedia within the next 30 days.
What airports do you fly into for Kona Coast from Chicago?
Kona Intl. Airport (KOA), Waimea-Kohala Airport (MUE) and Upolu Point, HI (UPP-Upolu) are your options when traveling from Chicago to Kona Coast. Around 9 mi west of the heart of Kona Coast, Kona Intl. Airport (KOA) is the city’s main hub. Keep in mind factors such as flight arrival and departure times and the distance to your hotel before choosing your airport. Makani Golf Club and Kailua-Kona Beaches are a couple of leading attractions to put on your must-see list when you get to your destination.
Can I change the date of my flight from Midway Airport to KOA?
Expedia makes it easy to make amendments to your Chicago Airport to KOA journey yourself. Log in to the Expedia Trips portal and click on “change flight.” Look for new flights and secure the one that works best. You’ll get an estimate of applicable flight change costs. Alternatively, use our Customer Service portal to chat to our Virtual Agent and quickly get answers to your questions.
Chicago nearby Airports
*Available to One Key members.