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$661+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
PER — CHI
may. 4 — may. 111
dom. 5/4
dom. 5/11
1 adult, Economy
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Cheapflights Tip: The best prices from Waikiki to Chicago are usually found in March or February, booked 15 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 abril 29, 2025.

Round-trip from

$1,270
(Expedia)

One-way from

$661
(Mytrip)

Popular in

June

Cheapest in

March

Average price

$1,589
From Waikiki to Chicago (CHI)
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One-way flight from Waikiki to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($47 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 29, 2025.

This Expedia deal was found by Cheapflights users on 4/28. 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.
mar. 7/2212:25 pmPER - ORD
2 stops33h 50mJapan Airlines
dom. 7/2712:30 pmORD - PER
2 stops47h 10mJapan Airlines
Deal found 4/28$1,270
This Trip.com deal was found by Cheapflights users on 4/28. 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.
jue. 6/128:30 pmPER - ORD
2 stops50h 10mMultiple Airlines
jue. 6/197:50 pmORD - PER
2 stops43h 40mMultiple Airlines
Deal found 4/28$1,518
This Flightnetwork deal was found by Cheapflights users on 4/28. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/129:35 pmPER - ORD
2 stops35h 36mANA
jue. 6/1911:50 amORD - PER
1 stop43h 10mANA
Deal found 4/28$1,719
This Aunt Betty deal was found by Cheapflights users on 4/28. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/2712:10 amPER - ORD
1 stop27h 15mCathay Pacific
mar. 6/34:00 pmORD - PER
1 stop41h 40mCathay Pacific
Deal found 4/28$1,730
This Booking.com deal was found by Cheapflights users on 4/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2911:35 pmPER - ORD
2 stops28h 14mAir Canada
mié. 8/610:50 amORD - PER
3 stops41h 10mAir Canada
Deal found 4/28$2,010
This oojo deal was found by Cheapflights users on 4/28. 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.
mar. 7/293:20 pmPER - ORD
1 stop36h 45mQatar Airways
mié. 8/611:52 amORD - PER
2 stops41h 48mQatar Airways
Deal found 4/28$2,079
This Jetabroad deal was found by Cheapflights users on 4/28. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/2912:25 pmPER - ORD
2 stops40h 20mEmirates
mié. 8/68:35 pmORD - PER
1 stop32h 00mEmirates
Deal found 4/28$2,120

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 abril 29, 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

mar. 7/22

12:25 pm-9:15 am

2 stops33h 50m

Chicago O'Hare Intl

dom. 7/27

12:30 pm-12:40 am

2 stops47h 10m

$1,270

PerthChicago

PER - ORD

PERORD

Perth

jue. 6/12

8:30 pm-9:40 am

2 stops50h 10m

Chicago O'Hare Intl

jue. 6/19

7:50 pm-4:30 am

2 stops43h 40m

$1,518

PerthChicago

PER - ORD

PERORD

Perth

jue. 6/12

9:35 pm-8:11 pm

2 stops35h 36m

Chicago O'Hare Intl

jue. 6/19

11:50 am-8:00 pm

1 stop43h 10m

$1,719

PerthChicago

PER - ORD

PERORD

Perth

mar. 5/27

12:10 am-2:25 pm

1 stop27h 15m

Chicago O'Hare Intl

mar. 6/3

4:00 pm-10:40 pm

1 stop41h 40m

$1,730

PerthChicago

PER - ORD

PERORD

Perth

mar. 7/29

11:35 pm-2:49 pm

2 stops28h 14m

Chicago O'Hare Intl

mié. 8/6

10:50 am-5:00 pm

3 stops41h 10m

$2,010

PerthChicago

PER - ORD

PERORD

Perth

mar. 7/29

3:20 pm-3:05 pm

1 stop36h 45m

Chicago O'Hare Intl

mié. 8/6

11:52 am-6:40 pm

2 stops41h 48m

$2,079

PerthChicago

PER - ORD

PERORD

Perth

mar. 7/29

12:25 pm-3:45 pm

2 stops40h 20m

Chicago O'Hare Intl

mié. 8/6

8:35 pm-5:35 pm

1 stop32h 00m

$2,120

PerthChicago

PER - ORD

PERORD

Perth

mié. 8/13

3:35 pm-11:31 pm

3 stops44h 56m

$661

PerthChicago

PER - ORD

PERORD

Perth

mié. 8/13

12:25 pm-9:15 am

2 stops33h 50m

$1,063

PerthChicago

PER - ORD

PERORD

Perth

mar. 5/27

12:10 am-2:25 pm

1 stop27h 15m

$1,068

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 14 results
1
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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 April 25, 2025.

To ensure you get the cheapest price possible for a flight from Waikiki to Chicago, you should look to book at least 15 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, August is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $245). Flying from Waikiki to Chicago in March is currently the most expensive (average of $321). 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.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

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.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated abril 29, 2025.
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Japan Airlines
8.3
Very good
1,459 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
ANA
8.3
Very good
855 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Singapore Airlines
8.1
Very good
1,292 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Emirates
8.0
Very good
3,213 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Finnair
7.6
Good
1,273 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Boarding

8.4

Entertainment

7.8

Crew

8.7

Food

7.7

Comfort

8.2

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.

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.

  • What are the cheapest airlines to fly from Waikiki to Chicago one-way?

    To fly one-way, consider booking your trip with Japan Airlines, which is currently one of the cheapest options available, starting at $1,063. Cathay Pacific flights start at $1,068 while deals on Singapore Airlines start at $1,800 one-way.

  • 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, August is the cheapest month in which you can book a flight from Waikiki to Chicago (average of $245). Flying from Waikiki to Chicago in March is currently the most expensive (average of $321). 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 Waikiki?

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

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 abril 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$1,184Average$1,404FlexibilityNo cancel feeOn-time71%

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