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$1,096+ Cheap flights from Waikiki, Australia to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
PER — CHI
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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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 January 29, 2026.

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.
Sat 2/79:55 pm
PER
-
ORD
2 stops45h 20m
ANA
Mon 2/2310:30 am
ORD
-
PER
1 stop43h 40m
ANA
Deal found 1/27$1,096
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/219:55 pm
PER
-
ORD
2 stops45h 10m
ANA
Fri 12/1110:30 am
ORD
-
PER
1 stop43h 40m
ANA
Deal found 1/27$1,141
This oojo 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:30 am
PER
-
ORD
2 stops35h 05m
Japan Airlines
Sun 4/121:05 am
ORD
-
PER
2 stops58h 35m
Japan Airlines
Deal found 1/28$1,290
This Japan 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 Japan Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/510:30 am
PER
-
ORD
2 stops41h 15m
Japan Airlines
Mon 3/911:35 am
ORD
-
PER
2 stops47h 20m
Japan Airlines
Deal found 1/26$1,300
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:45 pm
PER
-
ORD
2 stops64h 50m
Multiple Airlines
Fri 12/1111:30 pm
ORD
-
PER
2 stops35h 50m
Multiple Airlines
Deal found 1/27$1,304
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/810:30 am
PER
-
ORD
2 stops41h 15m
Japan Airlines
Sat 4/111:05 am
ORD
-
PER
2 stops40h 45m
Japan Airlines
Deal found 1/28$1,309
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/910:30 am
PER
-
ORD
2 stops35h 05m
Japan Airlines
Sat 4/111:05 am
ORD
-
PER
2 stops40h 45m
Japan Airlines
Deal found 1/28$1,341
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/712:25 am
PER
-
ORD
2 stops27h 20m
Japan Airlines
Tue 4/1412:10 pm
ORD
-
PER
2 stops29h 40m
Japan Airlines
Deal found 1/28$1,362

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 January 29, 2026.

Round-trip from

$1,290
(oojo)

Popular in

October

Cheapest in

May

Average price

$1,386
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 January 2026
Search Deals

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 January 29, 2026.
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

Thu 3/5

10:30 am-1:45 pm

2 stops41h 15m

Chicago O'Hare Intl

Mon 3/9

11:35 am-11:55 pm

2 stops47h 20m

$1,300

PerthChicago

PER - ORD

PERORD

Perth

Thu 7/2

6:05 pm-9:10 pm

2 stops64h 05m

Chicago O'Hare Intl

Sun 7/26

12:30 am-4:05 am

2 stops38h 35m

$1,416

PerthChicago

PER - ORD

PERORD

Perth

Wed 3/11

5:45 pm-1:04 pm

2 stops32h 19m

Chicago O'Hare Intl

Tue 4/14

1:36 pm-12:05 pm

2 stops33h 29m

$1,659

PerthChicago

PER - ORD

PERORD

Perth

Mon 3/9

11:45 pm-6:52 pm

2 stops32h 07m

Chicago O'Hare Intl

Wed 4/15

6:00 pm-2:40 pm

2 stops31h 40m

$1,699

PerthChicago

PER - ORD

PERORD

Perth

Mon 3/9

10:40 pm-1:04 pm

2 stops27h 24m

Chicago O'Hare Intl

Sat 4/11

2:56 pm-11:15 am

2 stops31h 19m

$1,706

PerthChicago

PER - ORD

PERORD

Perth

Tue 3/10

10:40 pm-1:04 pm

2 stops27h 24m

Chicago O'Hare Intl

Fri 4/10

4:30 pm-11:15 am

2 stops29h 45m

$1,706

PerthChicago

PER - ORD

PERORD

Perth

Mon 3/9

10:40 pm-1:04 pm

2 stops27h 24m

Chicago O'Hare Intl

Fri 4/10

4:30 pm-12:15 pm

2 stops30h 45m

$1,706

PerthChicago

PER - ORD

PERORD

Perth

Fri 3/6

10:40 pm-9:25 pm

2 stops36h 45m

Chicago O'Hare Intl

Sun 4/12

7:17 pm-1:35 pm

2 stops29h 18m

$1,711

PerthChicago

PER - ORD

PERORD

Perth

Thu 3/12

10:40 pm-1:04 pm

2 stops27h 24m

Chicago O'Hare Intl

Sun 4/12

7:17 pm-3:25 pm

2 stops31h 08m

$1,711

PerthChicago

PER - ORD

PERORD

Perth

Thu 3/12

12:25 am-2:45 pm

2 stops27h 20m

Chicago O'Hare Intl

Fri 3/20

6:40 pm-10:55 pm

2 stops39h 15m

$1,735

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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

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 $1,769). 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 32h 19m. Japan Airlines provides one of the quickest options available for as low as $1,659. 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 $1,769). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Japan AirlinesCheapest$965Average$973FlexibilityNo cancel feeOn-time79%

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