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Kailua

$303+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kailua are usually found in February or January, booked 44 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 June 18, 2025.

Round-trip from

$561
(Delta)

One-way from

$303
(Delta)

Popular in

December

Cheapest in

February

Average price

$940
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 ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:10 amORD - HNL
2 stops15h 26mDelta
Thu 9/44:09 pmHNL - ORD
2 stops15h 36mDelta
Deal found 6/16$595
This Alaska Airlines deal was found by Cheapflights users on 6/18. 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.
Thu 10/98:20 amORD - HNL
1 stop17h 45mAlaska Airlines
Sat 10/188:03 amHNL - ORD
1 stop15h 58mAlaska Airlines
Deal found 6/18$598
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/31:35 pmMDW - HNL
1 stop12h 25mSouthwest
Mon 9/811:35 amHNL - MDW
2 stops12h 35mSouthwest
Deal found 6/16$600
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/196:04 amMDW - HNL
1 stop12h 11mDelta
Tue 8/263:05 pmHNL - MDW
1 stop13h 11mDelta
Deal found 6/16$605
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/56:15 amORD - HNL
1 stop13h 05mSouthwest
Wed 8/208:10 amHNL - ORD
1 stop10h 30mSouthwest
Deal found 6/16$629
This Trip.com deal was found by Cheapflights users on 6/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/233:18 pmORD - HNL
1 stop18h 42mMultiple Airlines
Mon 7/282:05 pmHNL - ORD
1 stop19h 08mMultiple Airlines
Deal found 6/18$654
This American Airlines deal was found by Cheapflights users on 6/18. 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 11/1010:00 amORD - HNL
Nonstop9h 15mAmerican Airlines
Mon 11/177:50 pmHNL - ORD
1 stop13h 35mAmerican Airlines
Deal found 6/18$662
This Hawaiian Airlines deal was found by Cheapflights users on 6/16. 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.
Sun 11/309:00 amORD - HNL
1 stop11h 50mHawaiian Airlines
Fri 12/58:00 amHNL - ORD
1 stop11h 59mHawaiian Airlines
Deal found 6/16$678
This United Airlines deal was found by Cheapflights users on 6/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/97:40 pmORD - HNL
1 stop20h 37mUnited Airlines
Fri 8/151:35 pmHNL - ORD
2 stops17h 17mUnited Airlines
Deal found 6/16$712

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 June 18, 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

Fri 8/29

6:10 am-4:36 pm

2 stops15h 26m

Honolulu

Thu 9/4

4:09 pm-12:45 pm

2 stops15h 36m

$595

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 8/16

7:18 pm-10:15 pm

1 stop31h 57m

Honolulu

Sun 8/24

11:09 pm-7:03 am

1 stop26h 54m

$599

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 9/3

1:35 pm-9:00 pm

1 stop12h 25m

Honolulu

Mon 9/8

11:35 am-5:10 am

2 stops12h 35m

$600

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 8/19

6:04 am-1:15 pm

1 stop12h 11m

Honolulu

Tue 8/26

3:05 pm-9:16 am

1 stop13h 11m

$605

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 8/5

6:15 am-2:20 pm

1 stop13h 05m

Honolulu

Wed 8/20

9:05 pm-3:20 pm

2 stops13h 15m

$610

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 9/4

10:00 am-7:07 pm

1 stop14h 07m

Honolulu

Sat 9/13

7:50 am-11:59 pm

1 stop11h 09m

$615

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 7/23

3:18 pm-2:52 pm

2 stops28h 34m

Honolulu

Mon 7/28

2:05 pm-2:13 pm

1 stop19h 08m

$652

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 8/9

7:40 pm-11:17 am

1 stop20h 37m

Honolulu

Fri 8/15

1:35 pm-11:52 am

2 stops17h 17m

$712

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 9/4

7:15 am-7:05 pm

2 stops16h 50m

$303

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 9/4

9:30 am-7:05 pm

2 stops14h 35m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 16 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.

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 June 13, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 44 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 June 18, 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. 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 June 18, 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 June 18, 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
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,964 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,507 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,810 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Entertainment

7.1

Boarding

8.1

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 $303. Alaska Airlines flights start at $307 while deals on Southwest start at $317 one-way.

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $1,539 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 $465.

  • 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 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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Hawaiian AirlinesCheapest$361Average$825FlexibilityNo cancel feeOn-time85%
DeltaCheapest$395Average$581FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$419Average$640FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$422Average$671FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$559Average$758FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$777Average$1,129FlexibilityNo cancel feeOn-time69%

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