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$233+ 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to Kailua are usually found in February or January, booked 65 days in advance, depart on a Tuesday or Thursday 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$461
(Delta)

One-way from

$233
(Delta)

Popular in

December

Cheapest in

February

Average price

$588
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. 2% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. 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 3/56:45 amORD - HNL
2 stops19h 11mDelta
Sun 3/99:45 pmHNL - ORD
2 stops15h 36mDelta
Deal found 2/20$466
This Delta deal was found by Cheapflights users on 2/20. 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 3/510:19 amMDW - HNL
2 stops15h 37mDelta
Sun 3/910:31 pmHNL - MDW
2 stops14h 47mDelta
Deal found 2/20$466
This Mytrip deal was found by Cheapflights users on 2/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/710:27 pmORD - HNL
2 stops27h 23mMultiple Airlines
Tue 4/2211:15 pmHNL - ORD
3 stops26h 18mMultiple Airlines
Deal found 2/20$470
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 3/134:05 pmORD - HNL
1 stop23h 55mAlaska Airlines
Tue 3/1812:40 pmHNL - ORD
2 stops24h 36mAlaska Airlines
Deal found 2/20$475
This Southwest deal was found by Cheapflights users on 2/19. 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 3/65:45 amMDW - HNL
1 stop13h 50mSouthwest
Sun 3/91:55 pmHNL - MDW
1 stop16h 15mSouthwest
Deal found 2/19$485
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Tue 4/298:25 amORD - HNL
1 stop16h 16mAmerican Airlines
Tue 4/299:39 pmHNL - ORD
1 stop14h 45mAmerican Airlines
Deal found 2/20$518
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 10/115:50 pmORD - HNL
1 stop22h 05mHawaiian Airlines
Mon 10/209:15 pmHNL - ORD
1 stop14h 04mHawaiian Airlines
Deal found 2/20$520
This Southwest deal was found by Cheapflights users on 2/20. 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.
Fri 3/286:00 amORD - HNL
1 stop14h 25mSouthwest
Wed 4/28:30 amHNL - ORD
1 stop10h 25mSouthwest
Deal found 2/20$574
This United Airlines deal was found by Cheapflights users on 2/20. 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 8/277:15 amORD - HNL
1 stop16h 18mUnited Airlines
Thu 9/410:30 pmHNL - ORD
1 stop21h 41mUnited Airlines
Deal found 2/20$617
This Trip.com deal was found by Cheapflights users on 2/20. 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.
Sun 4/68:50 pmMDW - HNL
1 stop13h 10mMultiple Airlines
Sun 4/1310:35 pmHNL - MDW
1 stop25h 48mMultiple Airlines
Deal found 2/20$665

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 February 20, 2025.

Fly from

Chicago

Fly to

Kailua

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 3/5

6:45 am-9:56 pm

2 stops19h 11m

Honolulu

Sun 3/9

9:45 pm-6:21 pm

2 stops15h 36m

$466

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Wed 3/5

10:19 am-9:56 pm

2 stops15h 37m

Honolulu

Sun 3/9

10:31 pm-6:18 pm

2 stops14h 47m

$466

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/7

10:27 pm-8:50 pm

2 stops27h 23m

Honolulu

Tue 4/22

11:15 pm-6:33 am

3 stops26h 18m

$470

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Thu 3/13

4:05 pm-11:00 am

1 stop23h 55m

Honolulu

Tue 3/18

12:40 pm-6:16 pm

2 stops24h 36m

$475

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 3/6

5:45 am-3:35 pm

1 stop13h 50m

Honolulu

Sun 3/9

1:55 pm-11:10 am

1 stop16h 15m

$485

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 4/29

8:25 am-7:41 pm

1 stop16h 16m

Honolulu

Tue 4/29

9:39 pm-5:24 pm

1 stop14h 45m

$518

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Fri 3/28

6:00 am-3:25 pm

1 stop14h 25m

Honolulu

Wed 4/2

8:30 am-11:55 pm

1 stop10h 25m

$574

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 8/12

7:20 am-7:09 pm

1 stop16h 49m

Honolulu

Tue 8/26

11:50 am-11:46 am

2 stops18h 56m

$640

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 4/6

8:50 pm-5:00 am

1 stop13h 10m

Honolulu

Sun 4/13

10:35 pm-5:23 am

1 stop25h 48m

$665

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 3/8

6:45 am-10:46 pm

2 stops20h 01m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 18 results
1
2

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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 65 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 February 20, 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 February 20, 2025.

The most flights from CHI to K4I are scheduled on a Thursday (3 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 February 20, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Boarding

8.2

Food

7.1

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $233. American Airlines flights start at $262 while deals on Southwest start at $278 one-way.

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $1,451 for a flight from Chicago to Kailua. The cheapest flight overall is $502 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $422.

  • 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$413Average$720FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$421Average$639FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$421Average$662FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$522Average$759FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$881Average$1,127FlexibilityNo cancel feeOn-time69%
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