HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$649+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
PER — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Keep the following information in mind while searching for Waikiki to Chicago flight deals. Data was last updated October 30, 2025.

Round-trip from

$1,219
(SmartFares)

One-way from

$649
(Kiwi.com)

Popular in

December

Cheapest in

May

Average price

$1,444
From Waikiki to Chicago (CHI)
Search Deals
One-way flight from Waikiki to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($188 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($54 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find 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 October 30, 2025.

This BestPriceTravel deal was found by Cheapflights users on 10/28. 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 BestPriceTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/26:50 pmPER - ORD
2 stops42h 20mAir New Zealand
Sun 11/97:10 amORD - PER
2 stops43h 40mAir New Zealand
Deal found 10/28$1,129
This SmartFares deal was found by Cheapflights users on 10/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:15 amPER - ORD
2 stops26h 20mQantas Airways
Mon 12/227:47 pmORD - PER
2 stops56h 28mQantas Airways
Deal found 10/30$1,219
This Air New Zealand deal was found by Cheapflights users on 10/28. 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 Air New Zealand is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:50 pmPER - ORD
2 stops38h 40mAir New Zealand
Mon 11/101:00 pmORD - PER
2 stops37h 50mAir New Zealand
Deal found 10/28$1,237
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/24:45 pmPER - ORD
2 stops64h 50mMultiple Airlines
Sun 11/911:30 pmORD - PER
2 stops35h 45mMultiple Airlines
Deal found 10/28$1,324
This Qantas Airways deal was found by Cheapflights users on 10/30. 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 Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:00 amPER - ORD
3 stops29h 35mMultiple Airlines
Mon 12/222:50 pmORD - PER
2 stops26h 55mMultiple Airlines
Deal found 10/30$1,361
This Japan Airlines deal was found by Cheapflights users on 10/27. 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 Japan Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2010:30 amPER - ORD
2 stops35h 00mJapan Airlines
Mon 11/2410:20 amORD - PER
2 stops47h 35mJapan Airlines
Deal found 10/27$1,429
This Expedia deal was found by Cheapflights users on 10/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/212:25 amPER - ORD
1 stop26h 30mCathay Pacific
Mon 11/102:35 pmORD - PER
1 stop26h 20mCathay Pacific
Deal found 10/28$1,506
This Cathay Pacific deal was found by Cheapflights users on 10/27. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1912:25 amPER - ORD
1 stop26h 30mCathay Pacific
Mon 11/242:35 pmORD - PER
1 stop26h 20mCathay Pacific
Deal found 10/27$1,571

Cheapflights Fare Finder

 
Customize your flight search to find flights from Waikiki to Chicago 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 October 30, 2025.
Use the filters below to find and compare flights from Waikiki to Chicago that are best for you.

Fly from

Waikiki

Fly to

Chicago

Route

Depart

Return

Price

PerthChicago

PER - ORD

PERORD

Perth

Tue 12/9

7:15 am-7:35 pm

2 stops26h 20m

Chicago O'Hare Intl

Mon 12/22

7:47 pm-6:15 pm

2 stops56h 28m

$1,219

PerthChicago

PER - ORD

PERORD

Perth

Thu 11/20

10:30 am-7:30 am

2 stops35h 00m

Chicago O'Hare Intl

Mon 11/24

10:20 am-11:55 pm

2 stops47h 35m

$1,429

PerthChicago

PER - ORD

PERORD

Perth

Tue 4/14

1:10 am-2:25 pm

2 stops50h 15m

Chicago O'Hare Intl

Fri 5/15

4:00 pm-11:55 pm

2 stops42h 55m

$1,495

PerthChicago

PER - ORD

PERORD

Perth

Wed 4/15

9:15 am-2:25 pm

1 stop42h 10m

Chicago O'Hare Intl

Fri 5/15

4:00 pm-10:40 pm

1 stop41h 40m

$1,554

PerthChicago

PER - ORD

PERORD

Perth

Wed 11/19

12:25 am-12:55 pm

1 stop26h 30m

Chicago O'Hare Intl

Mon 11/24

2:35 pm-6:55 am

1 stop26h 20m

$1,571

PerthChicago

PER - ORD

PERORD

Perth

Wed 2/4

5:15 am-6:25 pm

3 stops51h 10m

$649

PerthChicago

PER - ORD

PERORD

Perth

Wed 12/31

7:20 am-1:26 pm

2 stops44h 06m

$1,259

PerthChicago

PER - ORD

PERORD

Perth

Wed 2/4

8:30 am-12:55 pm

1 stop42h 25m

$1,286

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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?

Use this chart to determine the optimal time to book a round-trip flight from Waikiki to Chicago. Price data was last updated on October 24, 2025.

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 December is currently the most expensive (average of $1,534). 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.

How much does it cost to fly round-trip 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?

    A quick flight from Waikiki to Chicago can take about 26h 20m. Qantas Airways provides one of the quickest options available for as low as $1,219. 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 December is currently the most expensive (average of $1,534). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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.
Perth to O'Hare Intl flights

Top airline flying from Waikiki to Chicago

Discover the top airline that operate flights from Waikiki to Chicago. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Japan AirlinesCheapest$965Average$973FlexibilityNo cancel feeOn-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.