How long is the flight from Waikiki to Chicago?

A quick flight from Waikiki to Chicago can take about 29h 55m. Japan Airlines provides one of the quickest options available for as low as $1,617. There are 10947 mi between Waikiki and Chicago. This flight may include one or multiple stops.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest time of day to fly from WK1 to CHI?

When flying from Waikiki to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Yes. In addition to deals on Waikiki to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Waikiki to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Waikiki to Chicago.

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

Yes. Cheapflights offers flight deals from Waikiki to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$663+ Flights from Waikiki to Chicago

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Waikiki to Chicago 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 Waikiki to Chicago are usually found in May or August, booked 21 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Waikiki to Chicago

Cheapest flights from Waikiki to Chicago
Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Wed 12/174:55 amPER - ORD

2 stops52h 40mMultiple Airlines

Wed 12/312:35 pmORD - PER

1 stop26h 20mMultiple Airlines

Deal found 12/16

$2,173

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

Thu 1/2910:30 amPER - ORD

2 stops35h 05mJapan Airlines

Thu 2/510:35 amORD - PER

2 stops47h 20mJapan Airlines

Deal found 12/15

$1,316

Thu 1/299:55 pmPER - ORD

1 stop29h 55mANA

Thu 2/57:10 amORD - PER

2 stops47h 00mANA

Deal found 12/15

$1,617

Thu 1/2910:55 pmPER - ORD

3 stops34h 45mAir Canada

Thu 2/52:00 pmORD - PER

3 stops34h 30mAir Canada

Deal found 12/15

$1,699

Wed 1/2812:25 amPER - ORD

1 stop26h 30mCathay Pacific

Thu 2/52:35 pmORD - PER

1 stop42h 20mCathay Pacific

Deal found 12/15

$2,010

Sat 3/710:20 pmPER - ORD

1 stop30h 25mEmirates

Wed 3/118:45 pmORD - PER

1 stop31h 35mEmirates

Deal found 12/15

$2,040

Sat 3/710:45 pmPER - ORD

1 stop30h 00mQatar Airways

Wed 3/114:19 pmORD - PER

2 stops30h 36mQatar Airways

Deal found 12/15

$2,466

Sat 3/75:05 pmPER - ORD

3 stops42h 51mSingapore Airlines

Wed 3/116:04 amORD - PER

2 stops41h 31mSingapore Airlines

Deal found 12/15

$2,523

Fri 3/612:25 amPER - ORD

2 stops27h 20mJapan Airlines

Wed 3/116:40 pmORD - PER

2 stops47h 15mJapan Airlines

Deal found 12/15

$1,460

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

Wed 12/174:55 amPER - ORD

2 stops52h 40mMultiple Airlines

Wed 12/312:35 pmORD - PER

1 stop26h 20mMultiple Airlines

Deal found 12/16

$2,173

Wed 1/2812:25 amPER - ORD

1 stop26h 30mCathay Pacific

Thu 2/52:35 pmORD - PER

1 stop42h 20mCathay Pacific

Deal found 12/15

$2,010

Thu 1/2910:30 amPER - ORD

2 stops35h 05mJapan Airlines

Thu 2/510:35 amORD - PER

2 stops47h 20mJapan Airlines

Deal found 12/15

$1,316

Thu 1/299:55 pmPER - ORD

1 stop29h 55mANA

Thu 2/57:10 amORD - PER

2 stops47h 00mANA

Deal found 12/15

$1,617

Thu 1/2910:30 pmPER - ORD

2 stops30h 11mAir Canada

Thu 2/52:00 pmORD - PER

3 stops34h 30mAir Canada

Deal found 12/15

$1,669

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

Sat 3/148:40 pmPER - ORD

3 stops48h 55mMultiple Airlines

Deal found 12/16

$663

Fri 3/1312:25 amPER - ORD

1 stop26h 30mCathay Pacific

Deal found 12/16

$1,319

Find flight deals from Waikiki to Chicago

Round-trip from	$1,316 (Bravofly)
One-way from	$663 (Kiwi.com)
Popular in	October
Cheapest in	May
Average price	$1,818

From Waikiki to Chicago (CHI)

Search Deals

One-way flight from Waikiki to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($125 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($48 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

PerthChicago

PER - ORD

PERORD

Perth

Thu 1/29

10:30 am-7:35 am

2 stops35h 05m

Chicago O'Hare Intl

Thu 2/5

10:35 am-11:55 pm

2 stops47h 20m

$1,316

PerthChicago

PER - ORD

PERORD

Perth

Fri 3/6

12:25 am-1:45 pm

2 stops27h 20m

Chicago O'Hare Intl

Wed 3/11

6:40 pm-6:55 am

2 stops47h 15m

$1,460

PerthChicago

PER - ORD

PERORD

Perth

Thu 1/29

9:55 pm-1:50 pm

1 stop29h 55m

Chicago O'Hare Intl

Thu 2/5

7:10 am-8:10 pm

2 stops47h 00m

$1,617

PerthChicago

PER - ORD

PERORD

Perth

Thu 1/29

10:55 pm-7:40 pm

3 stops34h 45m

Chicago O'Hare Intl

Thu 2/5

2:00 pm-2:30 pm

3 stops34h 30m

$1,699

PerthChicago

PER - ORD

PERORD

Perth

Wed 1/28

12:25 am-12:55 pm

1 stop26h 30m

Chicago O'Hare Intl

Thu 2/5

2:35 pm-10:55 pm

1 stop42h 20m

$2,010

PerthChicago

PER - ORD

PERORD

Perth

Sat 3/7

10:20 pm-2:45 pm

1 stop30h 25m

Chicago O'Hare Intl

Wed 3/11

8:45 pm-5:20 pm

1 stop31h 35m

$2,040

PerthChicago

PER - ORD

PERORD

Perth

Sat 3/7

10:45 pm-2:45 pm

1 stop30h 00m

Chicago O'Hare Intl

Wed 3/11

4:19 pm-11:55 am

2 stops30h 36m

$2,466

PerthChicago

PER - ORD

PERORD

Perth

Sat 3/7

5:05 pm-9:56 pm

3 stops42h 51m

Chicago O'Hare Intl

Wed 3/11

6:04 am-12:35 pm

2 stops41h 31m

$2,523

PerthChicago

PER - ORD

PERORD

Perth

Sat 3/14

8:40 pm-8:35 am

3 stops48h 55m

$663

PerthChicago

PER - ORD

PERORD

Perth

Fri 3/13

12:25 am-1:55 pm

1 stop26h 30m

$1,319

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Best time to book a flight from Waikiki to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Waikiki 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 Waikiki to Chicago

How far ahead should I book a flight from Waikiki to Chicago?

To ensure you get the cheapest price possible for a flight from Waikiki to Chicago, you should look to book at least 19 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 Waikiki to Chicago?

Currently, October is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $855). Flying from Waikiki to Chicago in January is currently the most expensive (average of $1,782). 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.

Related info for your journey

How long is the flight from Waikiki to Chicago?
A quick flight from Waikiki to Chicago can take about 29h 55m. Japan Airlines provides one of the quickest options available for as low as $1,617. There are 10947 mi between Waikiki and Chicago. This flight may include one or multiple stops.
Can I find deals for flights from Waikiki to Chicago that include hotel bookings?
Yes. In addition to deals on Waikiki to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Waikiki to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Waikiki to Chicago.
Can I find deals for business class flights from Waikiki to Chicago?
Yes. Cheapflights offers flight deals from Waikiki to Chicago 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 Waikiki to Chicago?
Currently, October is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $855). Flying from Waikiki to Chicago in January is currently the most expensive (average of $1,782). 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

Lansing

Merrillville

Hammond

Porter

Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Waikiki to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Japan Airlines	Cheapest$965	Average$973	FlexibilityNo cancel fee	On-time79%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$663+ Cheap flights from Waikiki, Australia to Chicago (CHI)

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.

Find cheap flights from Waikiki to Chicago with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Waikiki to Chicago are usually found in May or August, booked 21 days in advance, depart on a Wednesday or Tuesday and return on a Monday

Cheap flight deals from Waikiki to Chicago

Cheapest flights from Waikiki to ChicagoExplore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

Find flight deals from Waikiki to Chicago

Keep the following information in mind while searching for Waikiki to Chicago flight deals. Data was last updated December 16, 2025.

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 Waikiki to Chicago that are best for you.

Best time to book a flight from Waikiki to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Waikiki with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Waikiki to Chicago

How far ahead should I book a flight from Waikiki to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Waikiki to Chicago. Price data was last updated on December 12, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Waikiki to Chicago. 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 Waikiki to Chicago?

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

How can I find direct flights from Waikiki to Chicago?

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

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

Traveling to a place near Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Waikiki to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Waikiki to Chicago

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from Waikiki to Chicago
Explore the most affordable flight options available from Waikiki to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.