CHI - KOA

$219 Find Cheap Flights from Chicago to Kailua-Kona - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Kailua-Kona departing on 11/16. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$500
Typical prices: $494-$738
Alaska Airlines
Tue 9/22Wed 9/23
ORD - KOA • 1 stop
Cheapest non-stop
$1,172
United Airlines
Sat 1/2Sat 1/9
ORD - KOA • Non-stop
Nonstop flights
Not available
There are currently no direct flights between Chicago and Kailua-Kona. You'll need at least 1 connection.
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Top layover airports
San Diego (SAN)
Cheapest • Avg $440 (round-trip)
Honolulu (HNL)
Shortest trip • 11h 09m (one-way)
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Top routes
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When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 33% compared to booking last minute.
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When to travel
January
Cheapest • 28% price drop
March
Most popular
Good to know
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Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Kailua-Kona 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Tue, Sep 22 - Wed, Sep 23
Multiple Airlines Logo
8:00 am - 7:27 pmORD  Chicago O'Hare Intl-KOA Kona Intl
16h 27m1 stop Seattle/Tacoma Intl
Multiple Airlines Logo
8:00 am - 6:20 amKOA  Kona Intl-ORD Chicago O'Hare Intl
17h 20m2 stops Lihue Seattle/Tacoma Intl
$500Multiple Airlines
Fri, Nov 6 - Thu, Nov 12
Southwest Logo
10:05 am - 9:25 pmMDW  Chicago Midway-KOA Kona Intl
15h 20m2 stops Oakland Honolulu
Southwest Logo
9:30 pm - 11:50 amKOA  Kona Intl-MDW Chicago Midway
10h 20m1 stop Las Vegas Harry Reid Intl
$524Southwest
Tue, Nov 3 - Tue, Nov 10
Delta Logo
7:00 am - 6:38 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 38m1 stop Seattle/Tacoma Intl
Delta Logo
9:40 pm - 1:32 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 52m1 stop Los Angeles
$534Delta
Wed, Sep 9 - Wed, Oct 28
Delta Logo
7:00 am - 5:31 pmORD  Chicago O'Hare Intl-KOA Kona Intl
15h 31m1 stop Seattle/Tacoma Intl
Delta Logo
10:02 pm - 1:38 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
10h 36m1 stop Los Angeles
$534Delta
Sat, Oct 17 - Thu, Oct 22
Alaska Airlines Logo
2:21 pm - 2:43 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 22m1 stop San Diego
Alaska Airlines Logo
10:36 am - 1:25 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 49m1 stop San Diego
$574Alaska Airlines
Sat, Oct 17 - Fri, Oct 23
Alaska Airlines Logo
2:21 pm - 2:43 pmORD  Chicago O'Hare Intl-KOA Kona Intl
29h 22m1 stop San Diego
Alaska Airlines Logo
10:36 am - 1:25 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
21h 49m1 stop San Diego
$574Alaska Airlines
Mon, Nov 2 - Tue, Nov 10
American Airlines Logo
5:00 am - 3:02 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 02m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
10:21 pm - 2:43 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
12h 22m1 stop Phoenix Sky Harbor Intl
$594American Airlines
Mon, Oct 19 - Wed, Oct 28
American Airlines Logo
6:00 am - 3:17 pmORD  Chicago O'Hare Intl-KOA Kona Intl
14h 17m1 stop Los Angeles
American Airlines Logo
9:45 pm - 2:33 pmKOA  Kona Intl-ORD Chicago O'Hare Intl
11h 48m1 stop Phoenix Sky Harbor Intl
$594American Airlines
Thu, Dec 10 - Sat, Dec 19
United Airlines Logo
11:51 am - 8:32 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 41m1 stop San Francisco
United Airlines Logo
5:50 pm - 5:54 amKOA  Kona Intl-ORD Chicago O'Hare Intl
8h 04mnonstop
$774United Airlines
Thu, Dec 10 - Sat, Dec 19
United Airlines Logo
11:51 am - 8:32 pmORD  Chicago O'Hare Intl-KOA Kona Intl
12h 41m1 stop San Francisco
United Airlines Logo
5:50 pm - 5:54 amKOA  Kona Intl-ORD Chicago O'Hare Intl
8h 04mnonstop
$774United Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Kailua-Kona flights

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

How much is a round-trip flight from Chicago to Kailua-Kona?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago to Kailua-Kona departing in September.

Flight prices are below average for this route right now.

Flights to Kailua-Kona from Chicago usually cost between $614 and $780 in September.
The lowest price found in the past 5 days was $438 on American Airlines (Sep 9-Oct 28).

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

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago to Kailua-Kona costs $1,025 on the route between Chicago O'Hare Intl Airport (ORD) and Kailua-Kona (KOA). It is also the most popular route.

What is the cheapest month to fly from Chicago to Kailua-Kona?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Kailua-Kona, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Kailua-Kona is January, where tickets cost $536 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $1,103 and $947 respectively.

How far in advance should I book a flight from Chicago to Kailua-Kona?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Kailua-Kona, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago to Kailua-Kona, you should book around 4 weeks before departure, which saves you about 33% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

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Expert advice

Expert advice for your flight from Chicago to Kailua-Kona

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on KOA

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more

Good to know

Low season

January

Cheapest flight

$219
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago O'Hare Airport to Kailua-Kona

When to book flights from Chicago to Kailua-Kona

Are your dates flexible? Find out the best times to travel from Chicago to Kailua-Kona 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 Chicago to Kailua-Kona

  • Consider flying First Class when traveling with American Airlines from Chicago to Kailua-Kona. The airline's First Class ticket comes with priority privileges like speed through security, check-in and boarding at the airports, and priority bag handling after your flight. You also get to enjoy comfy seats, premium dining, and free in-flight entertainment.

    What are the common stopover options for flights from Chicago to Kailua Kona?

  • Flights from Chicago to Kailua Kona are generally connecting flights, as there are no direct flights at the moment. These flights have layovers in different cities depending on the airline. Most airlines flying from Chicago to Kailua-Kona have layovers in Seattle, Tacoma (SEA), Los Angeles (LAX), San Francisco (SFO), Atlanta (ATL), Honolulu (HNL), and Denver (DEN).

    Which airlines flying from Chicago to Kailua-Kona assist passengers with special needs?

  • Each airline flying from Chicago to Kailua-Kona offer assistance services for passengers with special needs. Every airline on this route runs a wheelchair assistance program to help travelers with reduced mobility easily get through the airport. If you need a wheelchair for your travel, we recommend informing your airline at least 48 hours before your flight to ensure it is available. These airlines also have attendants who assist passengers with special needs when boarding, moving to and from seats, or disembarking from planes.

    How can I get from the Kailua International Airport to Downtown Kailua-Kona?

  • There are several transportation options from Kona Airport to Kailua-Kona. Buses offer one of the most affordable and convenient ways of completing the trip from the airport to Kailua-Kona. Bus Line 202 runs from the airport to Luhia Street. The buses are operated by Hele-On Bus and depart the airport every 30 minutes. Alternatively, you can taxi or drive from the airport to Kailua-Kona.

    Which airlines flying from Chicago to Kailua-Kona offer better pet policies?

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

    In the last 5 days, the lowest price for a flight from Chicago to Kailua-Kona was $219 for a one-way ticket and $438 for a round-trip.

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

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

  • Which airports will I be using when flying from Chicago to Kailua-Kona?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Kona Intl.

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

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

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

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Chicago and Kailua-Kona, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Kailua-Kona, Southwest or Alaska Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Kailua-Kona are Southwest and Alaska Airlines. With an average price for the route of $744 and an overall rating of 8.0, Southwest is the most popular choice. Alaska Airlines is also a great choice for the route, with an average price of $722 and an overall rating of 7.9.

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

    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 Chicago to Kailua-Kona.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kailua-Kona from Chicago 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 Chicago to Kailua-Kona?

    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 Kailua-Kona with an airline and back to Chicago with another airline.

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

    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 Kailua-Kona from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

  • If you have a carry-on bag, consider flying with American Airlines on the NYC to BGR route. The airline allows you to board with one standard carry-on bag, which should have 40 lb at most of the weight. Its maximum dimensions must not exceed 22 x 14 x 9 inches. Also, you can have a personal item with sizes 18 x 14 x 8 inches, which must fit under the seat.
  • Flights from Chicago to Kailua-Kona depart from either Chicago O’Hare International Airport (ORD) or Chicago Midway Airport (MDW). Of the two Chicago airports, ORD handles more flights to Kailua-Kona than MDW. Therefore, consider flying from ORD to get more flight options.
  • Consider flying from Chicago MDW to Ellison Onizuka Kona International Airport (KOA) if you want to avoid long queues at the departure airport. MDW is usually less crowded than ORD. Therefore, you will spend less time getting through the airport for your flight.
  • Consider booking American Airlines or United when flying from Chicago ORD to Kailua-Kona. The airport is a hub for these two airlines; therefore, flying with them will give you more flight options. You will also get a way to access United Club and American Airlines Admirals Club at ORD by paying at the door.
  • You are welcome to use the pet relief areas at ORD when traveling with your pet from Chicago to Kailua-Kona. Outdoor pet relief areas are outside Door 1A, Door 2A, Door 5B, and near Lotto Booth in Terminal 1 Main Hall.

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

Information on your arrival and departure airports

Kailua-Kona (KOA)