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Kailua

$274+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
abr. 22 — abr. 291
mar. 4/22
mar. 4/29
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kailua are usually found in February or January, booked 53 days in advance, depart on a Thursday or Tuesday and return on a Monday

Cheap flight deals from Chicago to Kailua

Keep the following information in mind while searching for Chicago to Kailua flight deals. Data was last updated abril 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$429
(Delta)

One-way from

$274
(Delta)

Popular in

December

Cheapest in

February

Average price

$718
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
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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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Highest demand for flights based on searches. 3% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Chicago to Kailua

Cheapest flights from Chicago to Kailua
Explore the most affordable flight options available from Chicago to Kailua. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 17, 2025.

This Alaska Airlines deal was found by Cheapflights users on 4/15. 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. 5/69:00 amORD - HNL
1 stop15h 10mAlaska Airlines
lun. 5/1211:45 pmHNL - ORD
1 stop12h 15mAlaska Airlines
Deal found 4/15$423
This Delta deal was found by Cheapflights users on 4/15. 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. 5/66:45 amORD - HNL
2 stops17h 34mDelta
lun. 5/123:21 pmHNL - ORD
1 stop11h 28mDelta
Deal found 4/15$429
This Delta deal was found by Cheapflights users on 4/15. 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. 5/610:20 amMDW - HNL
2 stops15h 21mDelta
lun. 5/123:21 pmHNL - MDW
1 stop12h 19mDelta
Deal found 4/15$429
This eDestinos deal was found by Cheapflights users on 4/16. 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.
mar. 5/69:34 amMDW - HNL
3 stops41h 26mMultiple Airlines
lun. 5/1211:15 pmHNL - MDW
2 stops31h 11mMultiple Airlines
Deal found 4/16$524
This American Airlines deal was found by Cheapflights users on 4/16. 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.
sáb. 5/311:33 pmORD - HNL
1 stop12h 38mAmerican Airlines
sáb. 6/75:33 pmHNL - ORD
1 stop11h 37mAmerican Airlines
Deal found 4/16$540
This Hawaiian Airlines deal was found by Cheapflights users on 4/16. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/102:05 pmORD - HNL
1 stop11h 20mHawaiian Airlines
lun. 9/151:10 pmHNL - ORD
1 stop11h 30mHawaiian Airlines
Deal found 4/16$557
This Southwest deal was found by Cheapflights users on 4/17. 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. 9/89:10 pmMDW - HNL
1 stop18h 10mSouthwest
mar. 9/1611:35 amHNL - MDW
2 stops12h 25mSouthwest
Deal found 4/17$586

Cheapflights Fare Finder

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 2,558,603 searches. Data last updated abril 17, 2025.
Use the filters below to find and compare flights from Chicago to Kailua that are best for you.

Fly from

Chicago

Fly to

Kailua

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar. 5/6

9:00 am-7:10 pm

1 stop15h 10m

Honolulu

lun. 5/12

11:45 pm-5:00 pm

1 stop12h 15m

$423

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mar. 5/6

6:45 am-7:19 pm

2 stops17h 34m

Honolulu

lun. 5/12

3:21 pm-7:49 am

1 stop11h 28m

$429

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mar. 5/6

10:20 am-8:41 pm

2 stops15h 21m

Honolulu

lun. 5/12

3:21 pm-8:40 am

1 stop12h 19m

$429

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

mar. 5/6

9:34 am-10:00 pm

3 stops41h 26m

Honolulu

lun. 5/12

11:15 pm-11:26 am

2 stops31h 11m

$524

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sáb. 5/31

1:33 pm-9:11 pm

1 stop12h 38m

Honolulu

sáb. 6/7

5:33 pm-10:10 am

1 stop11h 37m

$540

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

lun. 5/5

9:25 pm-10:05 am

1 stop17h 40m

Honolulu

lun. 5/12

12:10 pm-5:15 am

1 stop12h 05m

$607

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

dom. 5/11

6:00 am-1:48 pm

1 stop12h 48m

Honolulu

dom. 5/25

11:45 pm-5:02 pm

1 stop12h 17m

$631

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

vie. 5/16

6:55 pm-10:05 am

2 stops20h 10m

Honolulu

vie. 5/23

11:15 am-12:45 pm

2 stops20h 30m

$674

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

sáb. 5/17

7:45 pm-4:16 pm

1 stop25h 31m

Honolulu

sáb. 5/24

9:40 pm-8:01 pm

2 stops17h 21m

$676

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

mié. 5/14

7:15 am-7:03 pm

1 stop16h 48m

$274

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Showing 1-10 of 18 results
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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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Kailua

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 April 11, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 53 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.

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Kailua (average of $469). Flying from Chicago to Kailua in June is currently the most expensive (average of $687). 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 abril 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Kailua as you normally would.

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 December 16, 2024.

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

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 abril 17, 2025.

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).

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 abril 17, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta 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.
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,380 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Boarding

8.1

Comfort

7.9

Crew

8.5

Entertainment

7.1

Food

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

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

    To fly one-way, consider booking your trip with Delta, which is currently one of the cheapest options available, starting at $274. Alaska Airlines flights start at $278 while deals on American Airlines start at $299 one-way.

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $2,285 for a flight from Chicago to Kailua. The cheapest flight overall is $277 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $417.

  • 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.

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Kailua (average of $469). Flying from Chicago to Kailua in June is currently the most expensive (average of $687). 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.

See more FAQs

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Top 6 airlines flying from Chicago to Kailua

Discover the top 6 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 2,558,603 searches. Data last updated abril 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$361Average$846FlexibilityNo cancel feeOn-time85%
DeltaCheapest$404Average$707FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$417Average$648FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$421Average$655FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$522Average$753FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$830Average$1,127FlexibilityNo cancel feeOn-time69%

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