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Kailua

$218+ 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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — HNL
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Kailua are usually found in February or January, booked 50 days in advance, depart on a Monday or Tuesday and return on a Wednesday

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 January 29, 2026.

This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 2/243:07 pm
ORD
-
HNL
1 stop25h 42m
Multiple Airlines
Tue 3/311:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/28$392
This Southwest deal was found by Cheapflights users on 1/29. 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 2/265:00 am
MDW
-
HNL
1 stop12h 15m
Southwest
Wed 3/49:55 pm
HNL
-
MDW
1 stop15h 35m
Southwest
Deal found 1/29$393
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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.
Sat 2/213:07 pm
ORD
-
HNL
1 stop32h 42m
Alaska Airlines
Tue 3/1010:35 pm
HNL
-
ORD
1 stop11h 23m
Alaska Airlines
Deal found 1/28$394
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 2/243:07 pm
ORD
-
HNL
2 stops19h 34m
Multiple Airlines
Tue 3/1010:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/28$399
This Aunt Betty deal was found by Cheapflights users on 1/27. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:20 am
ORD
-
HNL
1 stop32h 29m
Hawaiian Airlines
Tue 3/311:35 pm
HNL
-
ORD
1 stop11h 23m
Hawaiian Airlines
Deal found 1/27$400
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 2/243:07 pm
ORD
-
HNL
1 stop32h 42m
Alaska Airlines
Wed 3/411:35 pm
HNL
-
ORD
1 stop11h 23m
Alaska Airlines
Deal found 1/26$401
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Mon 4/276:00 am
ORD
-
HNL
1 stop12h 13m
Multiple Airlines
Thu 5/77:00 am
HNL
-
ORD
1 stop11h 59m
Multiple Airlines
Deal found 1/27$402
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 2/268:20 am
ORD
-
HNL
1 stop17h 06m
Multiple Airlines
Tue 3/1010:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/28$403
This Southwest deal was found by Cheapflights users on 1/27. 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 2/2610:15 pm
MDW
-
HNL
1 stop17h 00m
Southwest
Thu 3/52:50 pm
HNL
-
MDW
1 stop16h 15m
Southwest
Deal found 1/27$403
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 3/39:15 am
ORD
-
HNL
2 stops32h 57m
Multiple Airlines
Tue 3/107:50 am
HNL
-
ORD
1 stop15h 59m
Multiple Airlines
Deal found 1/28$406
This Alaska Airlines deal was found by Cheapflights users on 1/26. 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 2/243:07 pm
ORD
-
HNL
2 stops24h 36m
Multiple Airlines
Wed 3/411:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/26$408
This Alaska Airlines deal was found by Cheapflights users on 1/28. 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 2/233:07 pm
ORD
-
HNL
2 stops23h 02m
Multiple Airlines
Tue 3/1010:35 pm
HNL
-
ORD
1 stop11h 23m
Multiple Airlines
Deal found 1/28$409

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$392
(Alaska Airlines)

One-way from

$218
(Delta)

Popular in

June

Cheapest in

February

Average price

$641
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. 9% potential increase in price ($79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

MDW - HNL

MDWHNL

Chicago Midway

Thu 2/26

5:00 am-1:15 pm

1 stop12h 15m

Honolulu

Thu 3/5

2:50 pm-5:55 am

1 stop11h 05m

$393

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/20

7:24 pm-11:01 am

1 stop20h 37m

Honolulu

Thu 4/30

7:23 am-11:43 pm

1 stop11h 20m

$403

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 2/21

3:07 pm-7:49 pm

1 stop32h 42m

Honolulu

Wed 3/11

7:00 am-11:56 pm

1 stop11h 56m

$414

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 2/23

8:35 pm-11:15 am

1 stop18h 40m

Honolulu

Mon 3/2

8:05 am-12:25 am

1 stop12h 20m

$422

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 2/28

3:07 pm-9:26 pm

1 stop34h 19m

Honolulu

Wed 3/4

11:35 pm-2:58 pm

1 stop11h 23m

$423

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Wed 2/25

2:20 pm-9:54 pm

1 stop11h 34m

Honolulu

Mon 3/2

5:45 pm-1:29 pm

1 stop15h 44m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sun 4/12

7:20 am-3:01 pm

1 stop12h 41m

Honolulu

Fri 4/17

3:15 pm-7:40 am

1 stop11h 25m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 4/18

12:46 pm-9:20 pm

1 stop13h 34m

Honolulu

Tue 5/12

3:35 pm-10:00 am

1 stop13h 25m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 4/20

12:46 pm-9:20 pm

1 stop13h 34m

Honolulu

Wed 5/13

3:35 pm-10:00 am

1 stop13h 25m

$424

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 4/18

12:14 pm-9:45 pm

2 stops14h 31m

Honolulu

Wed 5/13

3:35 pm-10:00 am

1 stop13h 25m

$430

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 40 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 January 23, 2026.

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 50 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 January 29, 2026.

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.

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 January 29, 2026.

The most flights from CHI to K4I are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

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 January 29, 2026.
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
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Alaska Airlines
8.0
Very good
11,806 reviews
Alaska Airlines
8.0
Very good
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Southwest
8.0
Very good
4,267 reviews
Alaska Airlines
8.0
Very good
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
Delta
7.9
Good
8,128 reviews
Alaska Airlines
8.0
Very good
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
United Airlines
7.4
Good
9,215 reviews
Alaska Airlines
8.0
Very good
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading
American Airlines
7.2
Good
11,205 reviews
Alaska Airlines
8.0
Very good
11,806 reviews

Overall

8.0

Entertainment

7.0

Food

7.1

Crew

8.5

Boarding

8.1

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Jan 2026

STS - LAX

Enjoyed staff assistance from ticking thru tsa , boarding and in the plane Couldn’t pick a seat except upgrading

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 Southwest, Alaska Airlines, and Delta fly from Chicago to Kailua in about 11h 34m. The time it takes to get you to your destination can typically vary by up to 22h 45m. Chicago and Kailua are separated by a distance of 4234 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. Alaska Airlines flights start at $230 while deals on Hawaiian Airlines start at $231 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 United Airlines (77%), Air New Zealand (77%) and American Airlines (70%).

  • What are the cheapest flights from Chicago to Kailua?

    On average you can expect to pay $1,333 for a flight from Chicago to Kailua. The cheapest flight overall is $181 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $342.

  • 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$645FlexibilityNo cancel feeOn-timeN/A
Hawaiian AirlinesCheapest$331Average$699FlexibilityNo cancel feeOn-time85%
Alaska AirlinesCheapest$442Average$683FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$469Average$804FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$510Average$1,031FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$550Average$753FlexibilityNo cancel feeOn-time63%

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