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KOA - CHI

$247 Find Cheap Flights from Kailua-Kona to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kailua-Kona to Chicago departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kailua-Kona to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Kailua-Kona to Chicago, as well as popular online travel agencies
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Cheap Flight Deals from Kailua-Kona to Chicago (KOA-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Kailua-Kona to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Kailua-Kona to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Kailua-Kona to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:16 pm - 3:21 pmKOA-ORD
13h 05m2 stops
7:10 am - 2:20 pmORD-KOA
12h 10m1 stop
$490American Airlines
Find Deal
Tue, Apr 22 - Wed, Apr 30
9:16 pm - 3:21 pmKOA-ORD
13h 05m2 stops
5:00 am - 2:20 pmORD-KOA
14h 20m2 stops
$496American Airlines
Find Deal
Tue, Apr 22 - Wed, Apr 30
1:42 pm - 6:06 amKOA-ORD
11h 24m1 stop
6:00 am - 2:20 pmORD-KOA
13h 20m1 stop
$524American Airlines
Find Deal
Tue, Apr 22 - Wed, Apr 30
9:41 pm - 1:30 pmKOA-ORD
10h 49m1 stop
7:15 am - 5:30 pmORD-KOA
15h 15m1 stop
$593Delta
Find Deal
Tue, May 20 - Tue, Jun 3
9:41 pm - 1:30 pmKOA-ORD
10h 49m1 stop
9:00 am - 7:10 pmORD-KOA
15h 10m2 stops
$598Delta
Find Deal
Tue, May 20 - Tue, Jun 3
8:38 pm - 5:25 pmKOA-ORD
15h 47m2 stops
9:00 am - 7:10 pmORD-KOA
15h 10m2 stops
$615Delta
Find Deal
Tue, May 20 - Tue, Jun 3
9:30 pm - 10:30 pmKOA-ORD
20h 00m1 stop
6:00 am - 4:10 pmORD-KOA
15h 10m2 stops
$738Alaska Airlines
Find Deal
Thu, Jul 24 - Mon, Jul 28
5:59 am - 11:44 pmKOA-ORD
12h 45m2 stops
6:00 am - 4:10 pmORD-KOA
15h 10m2 stops
$744Alaska Airlines
Find Deal
Thu, Jul 24 - Mon, Jul 28
8:20 pm - 12:10 pmKOA-MDW
10h 50m1 stop
5:05 am - 2:15 pmMDW-KOA
14h 10m2 stops
$883Southwest
Find Deal
Wed, Jul 23 - Sun, Jul 27
8:20 pm - 1:20 pmKOA-MDW
12h 00m2 stops
6:25 am - 5:55 pmMDW-KOA
16h 30m2 stops
$889Southwest
Find Deal
Wed, Jul 23 - Sun, Jul 27

Flights from Kailua-Kona to Chicago - Travel Insights & Trends

Get data-powered insights and trends into flights from Kailua-Kona to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Kailua-Kona to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Kailua-Kona to Chicago.
Our data shows that the cheapest route for a return flight from Kailua-Kona to Chicago cost $1,135 and was between Kailua-Kona (KOA) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $1,135.

What’s the cheapest day of the week to fly from Kailua-Kona to Chicago?

The average price of all round-trip flights from Kailua-Kona to Chicago clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Chicago on a Monday and more expensive on a Saturday. On your return trip to Kailua-Kona, you should consider flying back on a Tuesday, and avoid Saturdays for better deals.

Good to know

Low season

August

High season

February

Cheapest flight

$247
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from Kailua-Kona to Chicago O'Hare Airport

When to book flights from Kailua-Kona to Chicago

Are your dates flexible? Find out the best times to travel from Kailua-Kona to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Kailua-Kona to Chicago

  • What is the cheapest flight from Kailua-Kona to Chicago?

    In the last 3 days, the lowest price for a flight from Kailua-Kona to Chicago was $247 for a one-way ticket and $490 for a round-trip.

  • Do I need a passport to fly between Kailua-Kona and Chicago?

    A passport is not required to fly from Kailua-Kona to Chicago.

  • Which aircraft models fly most regularly from Kailua-Kona to Chicago?

    The Boeing 787-8 Dreamliner is the aircraft model that flies most regularly on the Kailua-Kona to Chicago flight route.

  • Which airline alliances offer flights from Kailua-Kona to Chicago?

    Star Alliance is the only airline alliance operating flights between Kailua-Kona and Chicago.

  • On which days can I fly direct from Kailua-Kona to Chicago?

    You can catch a nonstop flight from Kailua-Kona to Chicago on on Saturday.

  • How does KAYAK find such low prices on flights from Kailua-Kona to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Kailua-Kona to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kailua-Kona to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Kailua-Kona is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Kailua-Kona to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Kailua-Kona with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kailua-Kona to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Kailua-Kona up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Kailua-Kona to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $515 or less one-way and $1,221 or less round-trip.

Prefer to fly direct from Kailua-Kona to Chicago?

Find which airlines fly direct from Kona Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Kona Intl to Chicago

Saturday

Lufthansa, United Airlines

Lufthansa, United Airlines

See more direct flights

Direct returns

Chicago to Kona Intl

Saturday

United Airlines

United Airlines

See more direct flights
See more direct flights

Top airline flying from Kailua-Kona to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Kailua-Kona to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Kailua-Kona to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
7.5Boarding
7.3Comfort
8.0Crew
6.5Food
7.0Entertainment
Airline reviews

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

10.0 ExcellentDr. Joseph, Feb 2025DCA - ORD
Read more American Airlines reviews

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

What, first class and not even a cup of coffee before landing at 5 am in First Class? Really?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

Everything you need to know for your flight from Kailua-Kona to Chicago

Information on your arrival and departure airports

Kailua-Kona (KOA)

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