How long is the flight from Chicago to Kailua?

Airlines like Alaska Airlines, Delta, and Southwest fly from Chicago to Kailua in about 16h 28m. The time it takes to get you to your destination can typically vary by up to 8h 37m. 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.

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.

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).

What are the cheapest flights from Chicago to Kailua?

On average you can expect to pay $2,177 for a flight from Chicago to Kailua. The cheapest flight overall is $266 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $447.

What are the most popular airlines that fly from Chicago to Kailua?

United Airlines, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Kailua.

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.

$247+ Flights from Chicago to Kailua

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

Airfare is below average for this route at the moment. Chicago to Kailua flights typically cost between $514 and $809 in January. The cheapest round-trip price found within the last 3 days was $473 on Delta (Jan 21-Jan 27).

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Find cheap flights from Chicago to Kailua with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Chicago to Kailua are usually found in October or February, booked 35 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

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 October 16, 2025.

Tue 11/187:47 amORD - HNL

2 stops18h 02mDelta

Sun 11/2311:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$489

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Mon 11/31:42 pmHNL - ORD

2 stops13h 46mMultiple Airlines

Deal found 10/14

$490

Wed 11/51:48 pmORD - HNL

2 stops25h 45mMultiple Airlines

Fri 11/149:35 pmHNL - ORD

1 stop21h 25mMultiple Airlines

Deal found 10/16

$493

Wed 11/57:37 amORD - HNL

2 stops17h 49mDelta

Mon 11/1011:25 pmHNL - ORD

2 stops15h 20mDelta

Deal found 10/15

$494

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Fri 11/77:43 amHNL - ORD

1 stop19h 45mMultiple Airlines

Deal found 10/14

$495

Sat 12/610:00 amORD - HNL

1 stop13h 05mAlaska Airlines

Sun 12/147:00 amHNL - ORD

1 stop11h 30mAlaska Airlines

Deal found 10/16

$496

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Wed 11/57:43 amHNL - ORD

2 stops22h 18mMultiple Airlines

Deal found 10/14

$497

Wed 12/107:50 amORD - HNL

2 stops17h 58mDelta

Sun 1/115:15 pmHNL - ORD

2 stops15h 26mDelta

Deal found 10/15

$498

Sat 11/155:23 amORD - HNL

2 stops18h 52mDelta

Sat 11/2211:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$499

Thu 11/275:23 amORD - HNL

1 stop13h 38mDelta

Sat 12/611:30 pmHNL - ORD

1 stop13h 45mDelta

Deal found 10/15

$500

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Mon 11/1011:13 pmHNL - ORD

1 stop26h 19mMultiple Airlines

Deal found 10/14

$501

Sun 11/168:00 amORD - HNL

1 stop16h 04mAlaska Airlines

Sat 11/227:00 amHNL - ORD

1 stop12h 59mAlaska Airlines

Deal found 10/15

$502

Best flights from Chicago to Kailua
Discover carefully curated flight deals from Chicago to Kailua that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 16, 2025.

Mon 1/122:06 pmORD - HNL

2 stops25h 05mAlaska Airlines

Sun 1/188:20 amHNL - ORD

1 stop11h 17mAlaska Airlines

Deal found 10/16

$492

Sat 11/157:47 amORD - HNL

1 stop16h 28mDelta

Sat 11/2211:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$494

Sat 2/288:55 pmMDW - HNL

1 stop18h 20mSouthwest

Mon 3/98:15 amHNL - MDW

1 stop15h 45mSouthwest

Deal found 10/14

$497

Tue 1/132:06 pmORD - HNL

2 stops25h 05mAlaska Airlines

Thu 1/228:20 amHNL - ORD

1 stop11h 17mAlaska Airlines

Deal found 10/16

$492

Thu 1/89:30 amMDW - HNL

2 stops15h 03mDelta

Thu 1/151:35 pmHNL - MDW

2 stops15h 15mDelta

Deal found 10/16

$494

Sun 1/188:10 amMDW - HNL

2 stops16h 50mSouthwest

Sat 1/249:55 pmHNL - MDW

1 stop10h 35mSouthwest

Deal found 10/14

$502

Mon 1/126:00 amMDW - HNL

1 stop13h 11mDelta

Wed 1/214:50 pmHNL - MDW

1 stop13h 06mDelta

Deal found 10/16

$497

Tue 12/28:59 pmORD - HNL

1 stop25h 07mAlaska Airlines

Tue 12/99:33 pmHNL - ORD

1 stop22h 26mAlaska Airlines

Deal found 10/16

$511

Thu 1/296:00 amMDW - HNL

1 stop13h 11mDelta

Tue 2/34:50 pmHNL - MDW

1 stop13h 06mDelta

Deal found 10/15

$497

Fri 11/146:00 amORD - HNL

1 stop33h 10mAlaska Airlines

Mon 11/179:55 pmHNL - ORD

1 stop14h 35mAlaska Airlines

Deal found 10/16

$520

Tue 1/136:00 amMDW - HNL

1 stop13h 11mDelta

Wed 1/214:50 pmHNL - MDW

1 stop13h 06mDelta

Deal found 10/16

$497

Thu 1/13:37 pmORD - HNL

1 stop30h 13mAlaska Airlines

Sun 1/118:20 amHNL - ORD

1 stop11h 17mAlaska Airlines

Deal found 10/15

$525

Tue 1/136:00 amMDW - HNL

1 stop13h 11mDelta

Mon 1/194:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$497

Fri 11/286:00 amORD - HNL

1 stop33h 10mAlaska Airlines

Wed 12/311:30 pmHNL - ORD

1 stop20h 20mAlaska Airlines

Deal found 10/16

$536

Sat 1/179:30 amMDW - HNL

2 stops15h 03mDelta

Mon 1/194:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$502

Wed 11/268:49 pmORD - HNL

1 stop25h 12mAlaska Airlines

Wed 12/37:45 pmHNL - ORD

2 stops20h 09mAlaska Airlines

Deal found 10/16

$539

Mon 1/129:20 amMDW - HNL

2 stops16h 10mDelta

Mon 1/194:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$502

Sun 1/119:30 amMDW - HNL

2 stops15h 03mDelta

Mon 1/194:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$502

Wed 1/149:30 amMDW - HNL

2 stops16h 00mDelta

Mon 1/194:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$502

Fri 1/169:30 amMDW - HNL

2 stops15h 03mDelta

Thu 1/224:45 pmHNL - MDW

1 stop12h 05mDelta

Deal found 10/16

$502

Thu 1/15:30 amORD - HNL

1 stop13h 34mDelta

Thu 1/89:55 pmHNL - ORD

1 stop11h 30mDelta

Deal found 10/16

$504

Wed 11/127:47 amORD - HNL

1 stop16h 28mDelta

Sat 11/2211:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$514

Thu 11/277:47 amORD - HNL

2 stops18h 02mDelta

Wed 12/311:30 pmHNL - ORD

1 stop20h 29mDelta

Deal found 10/16

$522

Last-minute flights from Chicago to Kailua
Discover last-minute flight deals from Chicago to Kailua. Data last updated October 16, 2025 and is based on user searches.

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Mon 11/31:42 pmHNL - ORD

2 stops13h 46mMultiple Airlines

Deal found 10/14

$490

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Fri 11/77:43 amHNL - ORD

1 stop19h 45mMultiple Airlines

Deal found 10/14

$495

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Wed 11/57:43 amHNL - ORD

2 stops22h 18mMultiple Airlines

Deal found 10/14

$497

Fri 10/316:30 amORD - HNL

1 stop19h 15mMultiple Airlines

Mon 11/1011:13 pmHNL - ORD

1 stop26h 19mMultiple Airlines

Deal found 10/14

$501

Mon 11/36:30 amORD - HNL

2 stops35h 55mMultiple Airlines

Sun 11/99:35 pmHNL - ORD

1 stop29h 53mMultiple Airlines

Deal found 10/15

$503

Wed 11/51:48 pmORD - HNL

2 stops25h 45mMultiple Airlines

Fri 11/149:35 pmHNL - ORD

1 stop21h 25mMultiple Airlines

Deal found 10/16

$493

Wed 11/57:37 amORD - HNL

2 stops17h 49mDelta

Mon 11/1011:25 pmHNL - ORD

2 stops15h 20mDelta

Deal found 10/15

$494

Sat 11/89:22 pmORD - HNL

1 stop27h 18mMultiple Airlines

Wed 11/129:35 pmHNL - ORD

1 stop21h 25mMultiple Airlines

Deal found 10/15

$498

Sat 11/155:23 amORD - HNL

2 stops18h 52mDelta

Sat 11/2211:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$499

Sun 11/168:00 amORD - HNL

1 stop16h 04mAlaska Airlines

Sat 11/227:00 amHNL - ORD

1 stop12h 59mAlaska Airlines

Deal found 10/15

$502

Tue 11/187:47 amORD - HNL

2 stops18h 02mDelta

Sun 11/2311:25 pmHNL - ORD

1 stop13h 53mDelta

Deal found 10/16

$489

Thu 11/275:23 amORD - HNL

1 stop13h 38mDelta

Sat 12/611:30 pmHNL - ORD

1 stop13h 45mDelta

Deal found 10/15

$500

One-way flights from Chicago to Kailua
Search for one-way flight options from Chicago to Kailua. Find affordable one-way fares based on user searches. Data last updated October 16, 2025.

Wed 11/129:22 pmORD - HNL

3 stops30h 07mMultiple Airlines

Deal found 10/14

$247

Thu 11/1310:00 amORD - HNL

1 stop14h 04mHawaiian Airlines

Deal found 10/14

$250

Mon 11/39:22 pmORD - HNL

2 stops25h 35mMultiple Airlines

Deal found 10/14

$251

Sun 11/167:47 amORD - HNL

1 stop16h 28mDelta

Deal found 10/15

$252

Tue 11/188:00 amORD - HNL

1 stop16h 04mAlaska Airlines

Deal found 10/16

$253

Mon 12/86:15 amMDW - HNL

3 stops37h 50mMultiple Airlines

Deal found 10/15

$253

Sun 11/169:22 pmORD - HNL

3 stops40h 13mMultiple Airlines

Deal found 10/14

$254

Mon 11/176:00 amORD - HNL

2 stops20h 36mMultiple Airlines

Deal found 10/16

$255

Tue 11/188:00 amORD - HNL

2 stops18h 47mMultiple Airlines

Deal found 10/14

$256

Sun 12/76:00 amMDW - HNL

2 stops18h 29mDelta

Deal found 10/15

$257

Wed 12/37:50 amORD - HNL

1 stop33h 10mDelta

Deal found 10/15

$258

Thu 11/137:47 amORD - HNL

2 stops18h 02mDelta

Deal found 10/15

$259

Cheap flight deals from Chicago to Kailua

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$473 (Delta)
One-way from	$247 (Kiwi.com)
Popular in	December
Cheapest in	October
Average price	$635

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. 5% potential increase in price ($45 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in October 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Mon 1/12

2:06 pm-11:11 am

2 stops25h 05m

Honolulu

Sun 1/18

8:20 am-11:37 pm

1 stop11h 17m

$492

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Tue 1/13

2:06 pm-11:11 am

2 stops25h 05m

Honolulu

Thu 1/22

8:20 am-11:37 pm

1 stop11h 17m

$492

ChicagoHonolulu

ORD - HNL

ORDHNL

Chicago O'Hare Intl

Sat 11/15

7:47 am-8:15 pm

1 stop16h 28m

Honolulu

Sat 11/22

11:25 pm-5:18 pm

1 stop13h 53m

$494

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/8

9:30 am-8:33 pm

2 stops15h 03m

Honolulu

Thu 1/15

1:35 pm-8:50 am

2 stops15h 15m

$494

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sat 2/28

8:55 pm-11:15 am

1 stop18h 20m

Honolulu

Mon 3/9

8:15 am-5:00 am

1 stop15h 45m

$497

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Mon 1/12

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Wed 1/21

4:50 pm-9:56 am

1 stop13h 06m

$497

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Thu 1/29

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Tue 2/3

4:50 pm-9:56 am

1 stop13h 06m

$497

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 1/13

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Wed 1/21

4:50 pm-9:56 am

1 stop13h 06m

$497

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Tue 1/13

6:00 am-3:11 pm

1 stop13h 11m

Honolulu

Mon 1/19

4:45 pm-8:50 am

1 stop12h 05m

$497

ChicagoHonolulu

MDW - HNL

MDWHNL

Chicago Midway

Sun 1/18

8:10 am-9:00 pm

2 stops16h 50m

Honolulu

Sat 1/24

9:55 pm-12:30 pm

1 stop10h 35m

$502

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 43 results

...

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?

To ensure you get the cheapest price possible for a flight from Chicago to Kailua, you should look to book at least 35 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 $362). 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?

Unlike at noon, when flights are generally more expensive, you can save up to 38% 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?

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.

Weekly flight availability from Chicago to Kailua

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).

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

Reviews of airlines servicing Kailua

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

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Alaska Airlines

8.0

Very good

11,100 reviews

Alaska Airlines

8.0

Very good

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Southwest

8.0

Very good

4,241 reviews

Alaska Airlines

8.0

Very good

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Delta

8.0

Very good

7,984 reviews

Alaska Airlines

8.0

Very good

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

United Airlines

7.4

Good

8,982 reviews

Alaska Airlines

8.0

Very good

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

American Airlines

7.2

Good

11,043 reviews

Alaska Airlines

8.0

Very good

11,100 reviews

Reviews

1 / 20

10.0

Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

How long is the flight from Chicago to Kailua?
Airlines like Alaska Airlines, Delta, and Southwest fly from Chicago to Kailua in about 16h 28m. The time it takes to get you to your destination can typically vary by up to 8h 37m. 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 flights from Chicago to Kailua?
On average you can expect to pay $2,177 for a flight from Chicago to Kailua. The cheapest flight overall is $266 while the most popular route, (Chicago O'Hare Intl - Honolulu) is currently priced at $447.
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 $362). 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Chicago to Kailua

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Peoria to Lihue flights

Springfield to Honolulu flights

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Evansville to Kahului flights

O'Hare Intl to Waimea (Big Island) flights

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St. Louis to Waimea (Big Island) flights

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Dubuque to Honolulu flights

Champaign to Kailua-Kona flights

Top 6 airlines flying from Chicago to Kailua

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$305	Average$578	FlexibilityNo cancel fee	On-timeN/A
Hawaiian Airlines	Cheapest$405	Average$744	FlexibilityNo cancel fee	On-time85%
Alaska Airlines	Cheapest$424	Average$668	FlexibilityNo cancel fee	On-time75%
American Airlines	Cheapest$436	Average$778	FlexibilityNo cancel fee	On-time71%
Southwest	Cheapest$553	Average$757	FlexibilityNo cancel fee	On-time63%
United Airlines	Cheapest$716	Average$1,104	FlexibilityNo cancel fee	On-time69%

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$247+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Chicago to Kailua with Cheapflights

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3. Compare prices and book

Cheapflights Tip: The best prices from Chicago to Kailua are usually found in October or February, booked 35 days in advance, depart on a Thursday or Tuesday and return on a Wednesday

Find flight deals from Chicago to Kailua

Cheapest flights from Chicago to KailuaExplore 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 October 16, 2025.

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 October 16, 2025.

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 October 16, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago to Kailua that are best for you.

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.

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 October 10, 2025.

What is the cheapest month to book a flight from Chicago to Kailua?

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 October 16, 2025.

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.

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 October 16, 2025.

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

Reviews of airlines servicing Kailua

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.

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?

What are the cheapest flights from Chicago to Kailua?

Can I find deals for flights from Chicago to Kailua that include hotel bookings?

How can I find direct flights from Chicago to Kailua?

Can I find deals for business class flights from Chicago to Kailua?

What is the cheapest month to book a flight from Chicago to Kailua?

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Alternative routes for Chicago to Kailua

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Top 6 airlines flying from Chicago to Kailua

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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 October 16, 2025.