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Flights from Chicago to Kailua-Kona

Cheap flight deals from Chicago to Kailua-Kona

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Chicago to Kailua-Kona?

We monitor flight fares to help you find the best deals effortlessly

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  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
  • 8 15
  • 15 22
  • 22 29

  • Jul

    29 6
  • 6 13
  • 13 20
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Kailua-Kona (KOA) the cheapest?

    Airlines adjust prices for flights from Chicago to Kailua-Kona based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Kailua-Kona (KOA) cost?

    According to Trip.com's data, the lowest price is around AED 3,051.

  • How long does it take to fly from Chicago (CHI) to Kailua-Kona (KOA)?

    It takes about 9 hours 3 minutes to fly from Chicago (CHI) to Kailua-Kona (KOA).

  • What are the most popular airlines that fly from Chicago (CHI) to Kailua-Kona (KOA)?

    Airlines with flights from Chicago (CHI) to Kailua-Kona (KOA): United Airlines.

  • How many airports are there in Kailua-Kona (KOA)?

    There are 1 airport(s) near Kailua-Kona (KOA): Kona International Airport.

How to find a cheap flight from Chicago to Kailua-Kona

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Kailua-Kona. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Kailua-Kona ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Kailua-Kona airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Wed, May 14 at AED 784 for one-way flights.
2
Compare cheap Chicago to Kailua-Kona flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Kailua-Kona. The cheapest airline operating is Spirit Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Kailua-Kona route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Kailua-Kona flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Kailua-Kona to get exclusive deals for you.

Flight Info | Chicago to Kailua-Kona

Cheapest one-way flight price AED 784
Cheapest return ticket price AED 4,519
Off-season for travel March
Peak season for travel January
Flight distance 6,793.37 km
Average flight time 9 hours 3 minutes
Popular airline Alaska Airlines

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