Question 1

What are the most popular routes to and from Kailua?

Accepted Answer

Travelers frequently search for route combinations, such as Kailua and London, Vancouver, Calgary, Los Angeles, Maui, San Francisco, New York, Kahului, Tokyo, Las Vegas, Portland, Bangkok, Montreal, San Diego, Auckland, Busan, Boston, San Jose, Zürich, Spokane.

Question 2

What are the most popular routes to and from Chicago?

Accepted Answer

Travelers frequently search for route combinations, such as Chicago and London, Mexico City, New York, Guadalajara, Edinburgh, Dallas, Manchester, Morelia, Atlanta, Los Angeles, Houston, León, Leeds, Orlando, San Francisco, Philadelphia, Tampa, Miami, Monterrey, Birmingham.

Question 3

What airports are near Kailua?

Accepted Answer

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

Question 4

What airports are near Chicago?

Accepted Answer

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

Question 5

Which airlines fly between Kailua and Chicago?

Accepted Answer

Currently, you can fly between Kailua and Chicago with Hawaiian Airlines, Frontier Airlines, United Airlines, Alaska Airlines, WestJet.

Question 6

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

Accepted Answer

If you don’t have specific dates for your trip between Kailua and Chicago, 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.

Question 7

What flights operate between Kailua and Chicago?

Accepted Answer

Traveling between Kailua and Chicago, 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.

Question 8

How many airports are there near Kailua?

Accepted Answer

There are a number of airports in and around Kailua. The main one is Kona International and other nearby airports include Kona International, Hilo International, Waimea-Kohala

Question 9

How many airports are there near Chicago?

Accepted Answer

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, Fort Wayne International, Dane County Regional, General Mitchell International, Quad City International, General Wayne A. Downing Peoria International, Muskegon County, Central Illinois Regional, University of Illinois Willard.

Question 10

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

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Kailua, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 11

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

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Question 12

What time do flights between Kailua and Chicago depart?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Kailua, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 13

What time do flights between Kailua and Chicago arrive?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Cheapest one-way trip	£194
Cheapest round-trip	£439
Average round-trip	£576
Most popular airline	Hawaiian Airlines

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Blue Line to downtown	40-50 min	$5 (standard fare)	every 5–10 min (traffic dependent)	budget travelers to Loop
Pace Bus 250 to Metra	60-90 min	$2-$5 (combined bus and Metra fare)	every 20–30 min (traffic dependent)	northwest suburbs connection
Taxi to downtown	35-70 min	$45-$65 (metered; varies by traffic)	on-demand 24/7 (traffic dependent)	door-to-door with luggage
Ride-hailing (Uber/Lyft)	35-70 min	$35-$75 (surge pricing may apply)	on-demand 24/7 (traffic dependent)	app-based convenience
Private transfer/shuttle	35-70 min	$60-$120 (pre-booked; fixed rate)	by reservation (traffic dependent)	groups or business travel

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Orange Line to downtown	25-30 min	$5 (standard fare)	every 6–12 min (traffic dependent)	quick access to Loop
Taxi to downtown	20-45 min	$30-$45 (metered; varies by traffic)	on-demand 24/7 (traffic dependent)	door-to-door convenience
Ride-hailing (Uber/Lyft)	20-45 min	$25-$50 (surge pricing may apply)	on-demand 24/7 (traffic dependent)	flexible pickup location

Airline	Mon 06.04	Tue 07.04	Wed 08.04	Thu 09.04	Fri 10.04	Sat 11.04	Sun 12.04
United Airlines	---	---	---	---	---	1	---
Weekly flights: 1 total	Daily flights: 0.14 average	Most flights: Saturday 1 flights

Airline	Mon 13.04	Tue 14.04	Wed 15.04	Thu 16.04	Fri 17.04	Sat 18.04	Sun 19.04
United Airlines	---	---	---	---	---	---	---
Weekly flights: 0 total	Daily flights: 0 average	Most flights: 0 flights

Cheap flights from Kailua to Chicago from £194

Explore flight deals to Chicago

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

How much do flights to Chicago cost?

Cheapest one-way trip

Cheapest round-trip

Average round-trip

Most popular airline

Getting from Chicago's airport to the city center

From O'Hare International Airport (ORD)

From Chicago Midway International Airport (MDW)

Key info about flying to Chicago

Weekly direct flights

Check-in for a flight from Kailua to Chicago

Weather in Chicago

Average Weather

14 day forecast

Frequently asked questions

Explore alternative trips

Start your next adventure now. Download our app and explore cheap flights effortlessly!

Company

Platform

Features

Discover

Name	Carrier code	IATA Code	Passport needed during booking
Hawaiian Airlines	HAL	HA	No
Frontier Airlines	FFT	F9	No
United Airlines	UAL	UA	No
Alaska Airlines	ASA	AS	No
WestJet	WJA	WS	No

Month	Average monthly max temperature	Average monthly min temperature
January	-1°C	-6°C
February	0°C	-5°C
March	6°C	0°C
April	11°C	4°C
May	17°C	10°C
June	22°C	16°C
July	26°C	20°C
August	25°C	19°C
September	22°C	16°C
October	15°C	10°C
November	8°C	3°C
December	2°C	-1°C