Cheap flights from Chicago to Kailua from £289

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1 stop
Tue, Nov 10
Chicago ORDKailua KOA
£289
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1 stop
Mon, Nov 9
Chicago ORDKailua KOA
£289
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1 stop
Tue, Nov 10
Chicago ORDKailua KOA
£290
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1 stop
Thu, Nov 12
Chicago ORDKailua KOA
£297
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1 stop
Wed, Nov 11
Chicago ORDKailua KOA
£297
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1 stop
Fri, Nov 13
Chicago ORDKailua KOA
£305
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1 stop
Mon, Nov 9 – Thu, Nov 12
Chicago ORDKailua KOA
£586
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1 stop
Mon, Nov 9 – Wed, Nov 11
Chicago ORDKailua KOA
£586
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1 stop
Tue, Nov 10 – Thu, Nov 12
Chicago ORDKailua KOA
£586
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1 stop
Mon, Nov 9 – Thu, Nov 12
Chicago ORDKailua KOA
£586
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1 stop
Tue, Nov 10 – Thu, Nov 12
Chicago ORDKailua KOA
£587
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1 stop
Thu, Nov 12 – Tue, Nov 17
Chicago ORDKailua KOA
£594
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How much do flights to Kailua cost?

Cheapest one-way trip

£289

Cheapest round-trip

£586

Average round-trip

£594

Most popular airline

Alaska Airlines

Key info about flying to Kailua

Depart from
O Hare International
Arrive to
Kona International
Average flights per week
285
Flight distance

Check-in for a flight from Chicago to Kailua

NameCarrier codeIATA CodePassport needed during booking
Alaska AirlinesASAASNo
Air CanadaACAACYes
Porter AirlinesPOEPDNo
United AirlinesUALUANo
WestJetWJAWSNo

Online check-in is not available for these airlines.

Weather in Kailua

Average Weather

MonthAverage monthly max temperatureAverage monthly min temperature
January23°C20°C
February23°C20°C
March23°C20°C
April24°C21°C
May24°C21°C
June25°C22°C
July26°C22°C
August26°C23°C
September26°C23°C
October26°C23°C
November25°C22°C
December24°C21°C
Hottest Month
26°C
August
Coldest month
20°C
February
Sunny days
183
days per year

14 day forecast

Friday
16 Oct
57%
27°C24°C
23 Oct
57%
27°C24°C
Saturday
17 Oct
59%
27°C24°C
24 Oct
74%
26°C25°C
Sunday
18 Oct
57%
27°C24°C
25 Oct
65%
27°C24°C
Monday
19 Oct
57%
27°C24°C
26 Oct
20%
27°C24°C
Tuesday
20 Oct
36%
27°C24°C
27 Oct
23%
26°C24°C
Wednesday
21 Oct
57%
27°C24°C
28 Oct
20%
26°C23°C
Thursday
22 Oct
41%
26°C24°C
29 Oct
26%
26°C23°C

Kailua travel tips

Cool off with shave ice

Hawaiian shave ice is a perfect treat for a humid day. Try a classic rock salt plum flavour or hunt for something more unique at one of the many shave ice shops throughout the town.

Spot a celebrity

It’s not uncommon to see a famous face in Kailua. The beautiful weather and warm, friendly atmosphere make it a favourite destination for celebrities to unwind and enjoy the laid back vibe.

Gambling is illegal in Hawaii

You won’t find any casinos in Kailua, as Hawaii is one of only two states in America where gambling is forbidden. Residents of Hawaii love to gamble, however, and often spend their holidays in Las Vegas to get their fix!

Travelers usually depart from O Hare International, Chicago Midway International, or Chicago Rockford International when they travel from Chicago to Kailua. The most popular airlines for this route are Alaska Airlines, Air Canada, Porter Airlines, United Airlines, and WestJet. Chicago and Kailua have 285 direct flights per week.

Frequently asked questions

What are the most popular routes to and from Chicago?

Travelers frequently search for route combinations, such as Chicago and Mexico City, London, Guadalajara, Morelia, New York, Orlando, León, Las Vegas, Dallas, Houston, Tampa, Los Angeles, Phoenix, Monterrey, Miami, Denver, Cancún, Istanbul, Atlanta, Calgary.

What are the most popular routes to and from Kailua?

Travelers frequently search for route combinations, such as Kailua and London, Vancouver, New York, San Diego, Portland, Los Angeles, Las Vegas, Salt Lake City, Honolulu, Auckland, San Francisco, San Jose, Phoenix, Bangkok, Seattle, Calgary, Kauai, Shanghai, Brisbane, Paris.

Which airports are there in Chicago?

Chicago is mainly served by O Hare International. But there are other airports nearby, including Chicago Midway International, Chicago Rockford International.

What airports are near Chicago?

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, South Bend International, Dane County Regional, General Mitchell International, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard.

What airports are near Kailua?

The main airport in Kailua is Kona International. It is also served by Kona International, Hilo International.

Which airlines fly between Chicago and Kailua?

Currently, you can fly between Chicago and Kailua with Alaska Airlines, Air Canada, Porter Airlines, United Airlines, WestJet.

When’s the best time to travel between Chicago and Kailua?

If you don’t have specific dates for your trip between Chicago and Kailua, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

What flights operate between Chicago and Kailua?

Traveling between Chicago and Kailua, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

How many airports are there near Chicago?

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, South Bend International, Dane County Regional, General Mitchell International, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard

How many airports are there near Kailua?

What time do nonstop (direct) flights between Chicago and Kailua depart?

What time do nonstop (direct) flights between Chicago and Kailua arrive?

What time do flights between Chicago and Kailua depart?

What time do flights between Chicago and Kailua arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.

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