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Kailua

$211+ 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 1/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Dec 28 — Jan 41
Sat 12/28
Sat 1/4
1 adult, Economy
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The best prices from Chicago to Kailua are usually found in January or February, booked 77 days in advance, depart on a Tuesday or Monday and return on a Sunday

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 December 23, 2024.

Round-trip from

$432
(Delta)

One-way from

$211
(Delta)

Popular in

December

Cheapest in

January

Average price

$1,100
From Chicago (CHI) to Kailua
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One-way flight from Chicago (CHI) to Kailua
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High demand for flights, 0% potential price rise
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Best time to find cheap flights, 4% potential price drop
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Average for round-trip flights in December 2024
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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 December 23, 2024.

This American Airlines deal was found by Cheapflights users on 12/21. 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.
Mon 12/308:30 amORD - HNL
1 stop14h 10mAmerican Airlines
Mon 1/1310:40 pmHNL - ORD
1 stop11h 09mAmerican Airlines
Deal found 12/21$738
This Alaska Airlines deal was found by Cheapflights users on 12/22. 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.
Mon 12/236:56 pmORD - HNL
1 stop19h 49mAlaska Airlines
Mon 1/133:31 pmHNL - ORD
1 stop22h 28mAlaska Airlines
Deal found 12/22$783
This Kissandfly.com deal was found by Cheapflights users on 12/22. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/309:35 pmORD - HNL
3 stops23h 47mMultiple Airlines
Sat 1/111:55 pmHNL - ORD
1 stop12h 00mMultiple Airlines
Deal found 12/22$869
This Southwest deal was found by Cheapflights users on 12/22. 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.
Mon 12/3010:45 pmMDW - HNL
1 stop16h 30mSouthwest
Sat 1/112:45 pmHNL - MDW
2 stops21h 50mSouthwest
Deal found 12/22$887
This Southwest deal was found by Cheapflights users on 12/22. 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.
Mon 12/307:10 pmORD - HNL
2 stops20h 05mSouthwest
Sat 1/112:45 pmHNL - ORD
2 stops22h 00mSouthwest
Deal found 12/22$892
This Delta deal was found by Cheapflights users on 12/21. 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.
Mon 12/307:00 amORD - HNL
1 stop11h 58mDelta
Mon 1/131:54 pmHNL - ORD
2 stops15h 22mDelta
Deal found 12/21$928
This Kissandfly.com deal was found by Cheapflights users on 12/22. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/307:35 amORD - HNL
1 stop14h 06mHawaiian Airlines
Sat 1/1110:21 pmHNL - ORD
1 stop12h 29mHawaiian Airlines
Deal found 12/22$936
This United Airlines deal was found by Cheapflights users on 12/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/237:10 amORD - HNL
2 stops17h 29mUnited Airlines
Thu 12/267:30 amHNL - ORD
1 stop12h 29mUnited Airlines
Deal found 12/22$1,005
This Delta deal was found by Cheapflights users on 12/22. 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.
Tue 12/249:30 amMDW - HNL
2 stops13h 47mDelta
Tue 12/316:39 pmHNL - MDW
1 stop12h 29mDelta
Deal found 12/22$1,078

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 2,558,603 searches. Data last updated December 23, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 5/1

6:00 am-2:30 pm

1 stop13h 30m

Honolulu

Mon 5/12

1:15 pm-6:05 am

1 stop11h 50m

$431

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 2/5

6:15 am-5:46 pm

2 stops15h 31m

Honolulu

Wed 2/12

4:50 pm-11:30 am

2 stops14h 40m

$432

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 2/5

9:33 am-10:01 pm

2 stops16h 28m

Honolulu

Thu 2/13

6:40 pm-1:05 pm

2 stops14h 25m

$432

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 1/19

6:55 pm-11:30 am

1 stop20h 35m

Honolulu

Sun 1/26

11:30 am-1:07 pm

1 stop21h 37m

$433

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 2/6

9:18 pm-5:53 pm

2 stops24h 35m

Honolulu

Thu 2/13

9:50 am-5:40 am

2 stops15h 50m

$437

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/23

6:00 am-2:56 pm

1 stop12h 56m

Honolulu

Wed 2/5

11:25 pm-12:17 am

2 stops20h 52m

$437

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/6

7:15 am-10:59 pm

3 stops19h 44m

Honolulu

Thu 2/13

12:15 pm-5:31 am

2 stops13h 16m

$489

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 1/15

12:56 pm-8:30 pm

1 stop11h 34m

Honolulu

Mon 2/3

10:40 pm-1:49 pm

1 stop11h 09m

$498

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 1/31

5:45 am-6:40 pm

2 stops16h 55m

Honolulu

Thu 2/6

2:45 pm-4:45 pm

2 stops22h 00m

$528

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/31

8:35 pm-3:20 pm

2 stops22h 45m

Honolulu

Thu 2/6

2:45 pm-1:35 pm

2 stops18h 50m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 19 results
1
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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.

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 December 20, 2024.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 77 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 December 23, 2024.

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 Wednesday at noon when fares are most often at their lowest. Sunday 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 December 23, 2024.

The most flights from CHI to K4I are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 December 23, 2024.
Peruse reviews from past customers who have flown with American 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.
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,780 reviews
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,549 reviews
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,588 reviews
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Hawaiian Airlines
7.9
Good
2,294 reviews
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
9,020 reviews
Southwest
8.1
Very good
4,780 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $211. Alaska Airlines flights start at $222 while deals on Hawaiian Airlines start at $246 one-way.

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $1,392 for a flight from Chicago to Kailua. The cheapest flight overall is $413 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $404.

  • 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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Alternative routes for Chicago to Kailua

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Chicago to Kailua

Discover the top 5 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 December 23, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$409Average$720FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$415Average$641FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$421Average$679FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$511Average$734FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$858Average$1,127FlexibilityNo cancel feeOn-time69%
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