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Kailua

$279+ 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 3/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kailua are usually found in January or February, booked 87 days in advance, depart on a Monday or Tuesday and return on a Monday

Cheap 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 18, 2025.

This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/257:25 amORD - HNL
2 stops18h 35mDelta
Wed 1/215:15 pmHNL - ORD
1 stop11h 25mDelta
Deal found 12/16$638
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:55 amORD - HNL
1 stop13h 11mMultiple Airlines
Tue 12/238:13 amHNL - ORD
1 stop31h 49mMultiple Airlines
Deal found 12/15$639
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/163:05 pmORD - HNL
1 stop25h 26mMultiple Airlines
Thu 12/181:43 pmHNL - ORD
1 stop11h 19mMultiple Airlines
Deal found 12/16$667
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Tue 12/1610:45 amORD - HNL
1 stop13h 54mUnited Airlines
Thu 12/186:05 pmHNL - ORD
Nonstop8h 11mUnited Airlines
Deal found 12/16$708
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/177:50 amORD - HNL
1 stop16h 39mDelta
Wed 12/2411:15 pmHNL - ORD
1 stop10h 31mDelta
Deal found 12/16$717
This Southwest deal was found by Cheapflights users on 12/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/168:55 pmMDW - HNL
1 stop18h 25mSouthwest
Tue 12/239:00 pmHNL - MDW
1 stop11h 45mSouthwest
Deal found 12/15$717
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:17 pmORD - HNL
2 stops20h 38mMultiple Airlines
Wed 12/2410:07 amHNL - ORD
1 stop30h 16mMultiple Airlines
Deal found 12/16$725
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:15 amORD - HNL
1 stop13h 33mUnited Airlines
Tue 1/67:30 amHNL - ORD
1 stop13h 28mUnited Airlines
Deal found 12/17$737
This Southwest deal was found by Cheapflights users on 12/16. 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 12/168:55 pmMDW - HNL
1 stop18h 25mSouthwest
Thu 12/188:00 amHNL - MDW
1 stop13h 30mSouthwest
Deal found 12/16$740
This United Airlines deal was found by Cheapflights users on 12/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:45 amORD - HNL
1 stop14h 03mUnited Airlines
Tue 1/67:30 amHNL - ORD
1 stop11h 29mUnited Airlines
Deal found 12/17$742
This Southwest deal was found by Cheapflights users on 12/16. 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 12/178:55 pmMDW - HNL
1 stop18h 25mSouthwest
Wed 12/249:00 pmHNL - MDW
1 stop14h 00mSouthwest
Deal found 12/16$770
This Southwest deal was found by Cheapflights users on 12/17. 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.
Thu 12/185:30 amMDW - HNL
1 stop12h 55mSouthwest
Thu 12/259:25 pmHNL - MDW
1 stop10h 50mSouthwest
Deal found 12/17$780

Find flight deals from Chicago to Kailua

Keep the following information in mind while searching for Chicago to Kailua flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$481
(Alaska Airlines)

One-way from

$279
(Delta)

Popular in

July

Cheapest in

January

Average price

$898
Provider with most accurate pricing for Chicago (CHI)-Honolulu flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Honolulu flights.
Search Deals
From Chicago (CHI) to Kailua
Search Deals
One-way flight from Chicago (CHI) to Kailua
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($92 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 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

Mon 1/19

9:00 am-9:21 pm

1 stop16h 21m

Honolulu

Sat 1/24

12:58 pm-11:37 pm

1 stop30h 39m

$484

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Fri 1/30

6:00 am-3:10 pm

1 stop13h 10m

Honolulu

Fri 2/6

4:45 pm-8:52 am

1 stop12h 07m

$487

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 4/22

7:15 am-7:21 pm

2 stops17h 06m

Honolulu

Fri 5/1

3:35 pm-10:00 am

1 stop13h 25m

$488

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 1/14

6:50 am-9:28 pm

2 stops18h 38m

Honolulu

Sun 1/18

4:44 pm-9:41 am

1 stop12h 57m

$493

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 2/8

7:20 am-3:56 pm

1 stop12h 36m

Honolulu

Sun 3/8

8:35 pm-6:00 pm

2 stops16h 25m

$493

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 1/21

7:20 am-9:28 pm

2 stops18h 08m

Honolulu

Sun 1/25

10:55 pm-5:44 pm

1 stop14h 49m

$493

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 1/29

5:30 am-3:10 pm

1 stop13h 40m

Honolulu

Tue 2/10

5:15 pm-1:13 pm

2 stops15h 58m

$494

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 1/7

7:20 am-9:28 pm

2 stops18h 08m

Honolulu

Wed 1/14

9:35 pm-5:44 pm

2 stops16h 09m

$494

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 1/31

11:45 am-9:28 pm

2 stops13h 43m

Honolulu

Wed 2/4

5:15 pm-9:08 am

1 stop11h 53m

$494

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 1/14

9:32 am-9:28 pm

2 stops15h 56m

Honolulu

Sun 1/18

5:15 pm-12:46 pm

2 stops15h 31m

$498

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 39 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 December 12, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 87 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, January is the cheapest month in which you can book a flight from Chicago to Kailua (average of $310). Flying from Chicago to Kailua in July is currently the most expensive (average of $663). 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 18, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 39% 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 December 16, 2024.

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

How much does it cost to fly round-trip from Chicago to Kailua?

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 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. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,477 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,005 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
United Airlines
7.4
Good
9,091 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
American Airlines
7.2
Good
11,054 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Food

7.1

Boarding

8.1

Entertainment

7.0

Crew

8.5

Overall

8.0

Comfort

7.8

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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.

  • How long is the flight from Chicago to Kailua?

    Airlines like Delta and Southwest fly from Chicago to Kailua in about 13h 10m. The time it takes to get you to your destination can typically vary by up to 3h 50m. Chicago and Kailua are separated by a distance of 4243 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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. American Airlines flights start at $215 while deals on Alaska Airlines start at $230 one-way.

  • What are the most reliable airlines from Chicago to Kailua?

    The top 3 most reliable airlines when flying from Chicago to Kailua are American Airlines (86%), Qantas Airways (86%) and Alaska Airlines (86%).

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $1,127 for a flight from Chicago to Kailua. The cheapest flight overall is $308 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $397.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Kailua (average of $310). Flying from Chicago to Kailua in July is currently the most expensive (average of $663). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$322Average$597FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$405Average$732FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$425Average$674FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$459Average$799FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$564Average$756FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$664Average$1,084FlexibilityNo cancel feeOn-time69%

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