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$227+ Cheap flights from Chicago (CHI) to Kailua, HI

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
set 11 — set 181
From?
To?
mer 9/11
mer 9/18
1 adult, Economy
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Find cheap flights from Chicago to Kailua with Cheapflights

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The best prices from Chicago to Kailua are usually found in January or November, booked 55 days in advance, depart on a Tuesday or Wednesday and return on a Friday

Cheap flight deals from Chicago to Kailua

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Kailua (K4I). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated settembre 6, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$401
(Alaska Airlines)

One-way from

$227
(Southwest)
High demand for flights, 24% potential price rise
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Best time to find cheap flights, 22% potential price drop
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From Chicago (CHI) to Kailua
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One-way flight from Chicago (CHI) to Kailua
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Cheap Chicago to Kailua flights in September & October 2024

Find cheap flight options from Chicago to Kailua specifically for the months of September and October 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,924,376 searches. Prices were last updated on settembre 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Kailua in 2024. More deals are always being added, so be sure to check back regularly.
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 10/265:45 pmORD - HNL
1 stop24h 35mAlaska Airlines
ven 11/11:15 pmHNL - ORD
1 stop11h 13mAlaska Airlines
Deal found 9/5$430
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 10/226:00 amORD - HNL
2 stops33h 00mAlaska Airlines
mer 10/302:56 pmHNL - ORD
1 stop28h 03mAlaska Airlines
Deal found 9/5$439
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 10/287:00 amORD - HNL
1 stop32h 39mAlaska Airlines
gio 10/318:13 pmHNL - ORD
1 stop22h 46mAlaska Airlines
Deal found 9/5$443
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 10/76:00 amORD - HNL
1 stop20h 45mAlaska Airlines
lun 10/212:23 pmHNL - ORD
1 stop21h 24mAlaska Airlines
Deal found 9/5$444
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 10/288:00 amORD - HNL
1 stop16h 13mAlaska Airlines
gio 10/313:55 pmHNL - ORD
2 stops32h 33mAlaska Airlines
Deal found 9/5$445
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 10/247:00 amORD - HNL
1 stop32h 40mAlaska Airlines
mar 11/122:15 pmHNL - ORD
1 stop11h 13mAlaska Airlines
Deal found 9/5$449
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 10/269:24 amMDW - HNL
2 stops16h 41mDelta
gio 10/313:40 pmHNL - MDW
1 stop12h 15mDelta
Deal found 9/3$449
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 10/268:40 amORD - HNL
2 stops30h 20mAlaska Airlines
mar 10/293:55 pmHNL - ORD
1 stop19h 53mAlaska Airlines
Deal found 9/5$450
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 9/95:25 pmORD - HNL
1 stop25h 45mAlaska Airlines
mer 10/212:50 pmHNL - ORD
1 stop11h 40mAlaska Airlines
Deal found 9/5$453

Chicago to Kailua 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Kailua in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,924,376 searches. Data last updated settembre 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to Kailua in 2024. More deals are always being added, so be sure to check back regularly.
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 10/265:45 pmORD - HNL
1 stop24h 35mAlaska Airlines
ven 11/11:15 pmHNL - ORD
1 stop11h 13mAlaska Airlines
Deal found 9/5$430
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 11/125:54 pmORD - HNL
1 stop32h 19mAlaska Airlines
mer 11/2011:33 pmHNL - ORD
1 stop25h 27mAlaska Airlines
Deal found 9/5$437
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 11/117:00 amORD - HNL
1 stop32h 39mAlaska Airlines
gio 11/212:15 pmHNL - ORD
1 stop11h 13mAlaska Airlines
Deal found 9/5$438
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 11/129:20 amMDW - HNL
2 stops16h 30mDelta
gio 11/214:50 pmHNL - MDW
1 stop11h 55mDelta
Deal found 9/4$438
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 10/226:00 amORD - HNL
2 stops33h 00mAlaska Airlines
mer 10/302:56 pmHNL - ORD
1 stop28h 03mAlaska Airlines
Deal found 9/5$439
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 11/117:00 amORD - HNL
1 stop32h 39mAlaska Airlines
gio 11/147:00 amHNL - ORD
1 stop25h 09mAlaska Airlines
Deal found 9/5$443
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 11/15:57 pmORD - HNL
1 stop23h 18mAlaska Airlines
gio 11/711:33 pmHNL - ORD
1 stop25h 27mAlaska Airlines
Deal found 9/5$444
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 10/287:19 pmORD - HNL
1 stop28h 54mAlaska Airlines
gio 10/313:55 pmHNL - ORD
2 stops32h 33mAlaska Airlines
Deal found 9/5$445
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 11/128:55 amORD - HNL
2 stops16h 55mDelta
gio 11/214:50 pmHNL - ORD
1 stop10h 36mDelta
Deal found 9/5$448

Chicago to Kailua flights leaving soon

Find last-minute flight options from Chicago to Kailua for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,924,376 searches. Data last updated settembre 6, 2024.
Book one of these great deals on flights from Chicago to Kailua. Users should examine the flight details to ensure there are no surprises.
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/128:20 amORD - HNL
1 stop11h 35mDelta
mar 9/179:15 pmHNL - ORD
1 stop10h 05mDelta
Deal found 9/5$472
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/126:00 amORD - HNL
2 stops17h 30mDelta
mar 9/179:15 pmHNL - ORD
1 stop10h 05mDelta
Deal found 9/5$477
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/126:00 amORD - HNL
2 stops17h 30mDelta
mar 9/1712:35 pmHNL - ORD
2 stops13h 51mDelta
Deal found 9/5$482
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/129:32 amMDW - HNL
2 stops16h 32mDelta
mer 9/1812:35 pmHNL - MDW
2 stops15h 06mDelta
Deal found 9/5$482
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 9/108:25 amMDW - HNL
1 stop15h 05mSouthwest
mar 9/178:35 amHNL - MDW
1 stop10h 30mSouthwest
Deal found 9/5$514
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 9/166:35 amORD - HNL
1 stop17h 22mDelta
mer 9/183:35 pmHNL - ORD
1 stop10h 51mDelta
Deal found 9/5$524
This eDestinos deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 9/166:40 amORD - HNL
2 stops31h 52mMultiple Airlines
ven 9/203:50 pmHNL - ORD
2 stops27h 38mMultiple Airlines
Deal found 9/5$526
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 9/166:35 amORD - HNL
1 stop17h 22mDelta
lun 9/2312:35 pmHNL - ORD
2 stops13h 51mDelta
Deal found 9/5$529
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 9/137:09 amORD - HNL
1 stop11h 46mAmerican Airlines
ven 9/203:25 pmHNL - ORD
1 stop16h 37mAmerican Airlines
Deal found 9/5$530

One-way flights to Kailua from Chicago

Search for one-way flight options from Chicago to Kailua. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,924,376 searches. Data last updated settembre 6, 2024.
If you're seeking multiple options on one-way flights from Chicago to Kailua, be sure to check out these deals, which are updated often. Those seeking round-trip flights from Chicago to Kailua should utilize the search form at the the top of the page.
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 11/48:40 pmMDW - HNL
1 stop18h 35mSouthwest
Deal found 9/5$227
This Southwest deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/266:15 amORD - HNL
2 stops15h 45mSouthwest
Deal found 9/5$232
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/269:21 amMDW - HNL
2 stops16h 43mDelta
Deal found 9/5$232
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/197:03 amORD - HNL
1 stop12h 02mDelta
Deal found 9/5$236
This Alaska Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 10/67:00 amORD - HNL
2 stops21h 59mAlaska Airlines
Deal found 9/5$238
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/85:45 amORD - HNL
2 stops16h 15mSouthwest
Deal found 9/4$241
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 11/35:20 amORD - HNL
2 stops17h 16mDelta
Deal found 9/4$248
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/266:00 amMDW - HNL
1 stop12h 32mDelta
Deal found 9/5$256
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 10/29:32 amMDW - HNL
2 stops16h 32mDelta
Deal found 9/5$261

Find flights from Chicago to Kailua within your budget

Customize your flight search to find flights from Chicago to Kailua that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,924,376 searches. Data last updated settembre 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$401 - $468

Route

Depart

Return

Price

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar 1/21

2 stops23h 56m

Honolulu

mar 1/28

1 stop21h 00m

$401

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar 1/21

2 stops23h 56m

Honolulu

mar 1/28

2 stops20h 10m

$406

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar 1/28

1 stop15h 03m

Honolulu

mer 2/12

1 stop15h 29m

$407

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sab 10/19

2 stops21h 42m

Honolulu

gio 10/24

3 stops30h 26m

$424

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mer 11/13

1 stop15h 00m

Honolulu

mar 11/19

1 stop15h 10m

$428

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

gio 11/14

1 stop12h 52m

Honolulu

sab 11/23

1 stop10h 15m

$433

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

lun 10/7

1 stop29h 18m

Honolulu

lun 10/21

2 stops14h 00m

$441

Chicago O'Hare IntlHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mer 1/8

1 stop16h 51m

Honolulu

mer 1/15

1 stop11h 14m

$447

Chicago MidwayHonolulu

MDW - HNL

MDWHNL

Chicago Midway

gio 10/24

1 stop17h 30m

Honolulu

lun 10/28

2 stops19h 55m

$468

Flights are sorted by cheapest first

Deals found on 9/4

Best time to book a flight from Chicago to Kailua

Have a flexible travel schedule? Discover the best time to fly to Kailua from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago to Kailua

Get recent, data-driven insights about flights from Chicago to Kailua including ideal travel times, pricing trends, and more.

How far ahead should I book a flight from Chicago to Kailua?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Kailua. Price data was last updated on August 30, 2024.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 55 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Find deals

What is the cheapest month to book a flight from Chicago to Kailua?

Currently, January is the cheapest month in which you can book a flight from Chicago to Kailua (average of $396). Flying from Chicago to Kailua in June is currently the most expensive (average of $606). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to K4I?

Find hourly flight availability from Chicago to Kailua. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated settembre 6, 2024.

Unlike at noon, when flights are generally more expensive, you can save up to 98% on flights from Chicago to Kailua by exploring options for tickets in the evening.

What is the cheapest day to fly from Chicago to Kailua?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Kailua. Price data was last updated on September 1, 2024.

Travelers seeking maximum savings on their Chicago to Kailua flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Find deals

Weekly flight availability from Chicago to Kailua

Explore weekly flight availability from Chicago to Kailua. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated settembre 6, 2024.

The most flights from CHI to K4I are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

What are the most popular airlines that fly from Chicago to Kailua?

Our users search for these airlines the most when looking for flights from Chicago to Kailua. Data last updated on settembre 6, 2024.

United Airlines, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Kailua.

United Airlines

United Airlines

From $653

American Airlines

American Airlines

From $425

Alaska Airlines

Alaska Airlines

From $399

Delta

Delta

From $403

Rainfall in Kailua by month

Plan your trip to Kailua by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Kailua ranges from 0.3 - 3.2 inches per month. December is typically the wettest month, when rainfall can reach 3.2 in. June is typically the driest time to visit Kailua when rainfall is around 0.3 in.

Temperature in Kailua by month

Plan your trip to Kailua by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Kailua, use this chart to help with planning. For those seeking warmer temperatures, August is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 73.4 F).

Reviews of airlines servicing Kailua

Get insights into the airlines that provide service to Kailua. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Kailua. Reviews last updated settembre 6, 2024.
Peruse reviews from past customers who have flown with Alaska Airlines, United Airlines and American Airlines from Chicago to Kailua to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.2
Very good
5,383 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,356 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
9,185 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,648 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.3
Good
10,000 reviews
Southwest
8.2
Very good
5,383 reviews

Comfort

8.1

Food

7.3

Entertainment

7.8

Crew

8.7

Boarding

8.3

Overall

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Chicago to Kailua. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find flights from Chicago to Kailua for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago to Kailua for under $500. The cheapest flight booked recently is on Alaska Airlines for just $401, but on average you can expect to pay $420.

  • Are there nonstop flights from Chicago to Kailua for under $1,000 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Kailua under $1,000. A good price for a nonstop flight from Chicago to Kailua is less than $1,108.

  • Are there last-minute flights available from Chicago to Kailua for under $500?

    There are currently 20+ open flights from Chicago to Kailua within the next 7 days for less than $500.

  • What are the cheapest airlines to fly from Chicago to Kailua one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $227. Delta flights start at $232 while deals on Alaska Airlines start at $238 one-way.

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $2,094 for a flight from Chicago to Kailua. The cheapest flight overall is $385 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $407.

  • What does ORD to HNL mean?

    Great question - ORD to HNL just means Chicago O'Hare Intl Airport to Honolulu Airport. Now you’ll know what these unique codes when you look for flights! Ready for more IATA code knowledge? These are related airports for your current travel destination: Kapolei Kalaeloa Airport (JRF), Mokuleia Dillingham Airfield Airport (HDH), Kaneohe Marine Corps Air Station Kaneohe Bay Airport (NGF), Kaneohe Barbers Point Airport (NAX).

  • Can I find deals for flights from Chicago to Kailua that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Kailua flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Kailua with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Kailua flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Kailua that include hotel bookings?

    Yes. In addition to deals on Chicago to Kailua flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Kailua?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Kailua.

  • Can I find deals for business class flights from Chicago to Kailua?

    Yes. Cheapflights offers flight deals from Chicago to Kailua by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Kailua that allow pets onboard?

    Many airlines flying from Chicago to Kailua offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Kailua?

    Yes, you can often find last-minute deals on Chicago to Kailua flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Kailua flight deals updated?

    The Chicago to Kailua flight deals you see on this page were last updated on 9/5.

  • What is the cheapest month to book a flight from Chicago to Kailua?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Kailua (average of $396). Flying from Chicago to Kailua in June is currently the most expensive (average of $606). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Kailua
See prices for flight routes from nearby airports that may be better suited for you.

O'Hare Intl to Honolulu flights
O'Hare Intl to Kahului flights
Midway to Honolulu flights
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Moline to Kahului flights
O'Hare Intl to Waimea (Kamuela) flights
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Moline to Kailua-Kona flights
Peoria to Kahului flights
Springfield to Honolulu flights
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St. Louis to Waimea (Kamuela) flights
Bloomington to Kahului flights
Bloomington to Lihue flights
Decatur to Honolulu flights
Evansville to Kahului flights
Champaign to Honolulu flights
Champaign to Kailua-Kona flights
Springfield to Lihue flights
Springfield to Kahului flights
Moline to Hilo flights
St. Louis to Kapalua flights
Dubuque to Honolulu flights
Evansville to Lihue flights

Top 4 airlines flying from Chicago to Kailua

Discover the top 4 airlines that operate flights from Chicago to Kailua. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,924,376 searches. Data last updated settembre 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$399Average$635FlexibilityNo cancel feeOn-time75%
DeltaCheapest$403Average$738FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$425Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$653Average$1,053FlexibilityNo cancel feeOn-time69%
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