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$673+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
PER — CHI
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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The best prices from Waikiki to Chicago are usually found in May 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 February 23, 2025.

Round-trip from

$1,261
(Qantas Airways)

One-way from

$673
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$1,352
From Waikiki to Chicago (CHI)
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One-way flight from Waikiki to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($110 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Qantas Airways deal was found by Cheapflights users on 2/20. 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.
Fri 3/218:00 amPER - ORD
2 stops28h 59mQantas Airways
Fri 3/288:20 pmORD - PER
2 stops27h 15mQantas Airways
Deal found 2/20$1,261
This Trip.com deal was found by Cheapflights users on 2/22. 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.
Mon 4/78:50 pmPER - ORD
2 stops61h 10mMultiple Airlines
Sun 4/1312:30 amORD - PER
2 stops36h 10mMultiple Airlines
Deal found 2/22$1,331
This Booking.com deal was found by Cheapflights users on 2/21. 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.
Thu 10/3010:55 pmPER - ORD
3 stops33h 37mAir Canada
Mon 11/33:40 pmORD - PER
2 stops34h 15mAir Canada
Deal found 2/21$1,472
This KAYAK deal was found by Cheapflights users on 2/21. 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.
Wed 10/2912:15 amPER - ORD
2 stops45h 10mJapan Airlines
Mon 11/310:20 amORD - PER
2 stops47h 35mJapan Airlines
Deal found 2/21$1,494
This Gurufare deal was found by Cheapflights users on 2/21. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/309:55 pmPER - ORD
1 stop29h 55mANA
Mon 11/34:25 pmORD - PER
2 stops61h 55mANA
Deal found 2/21$1,704
This oojo deal was found by Cheapflights users on 2/21. 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 4/710:45 pmPER - ORD
2 stops55h 54mQatar Airways
Mon 4/147:20 pmORD - PER
1 stop34h 20mQatar Airways
Deal found 2/21$1,729
This Emirates deal was found by Cheapflights users on 2/21. 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 Emirates is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/306:00 amPER - ORD
1 stop46h 45mEmirates
Mon 11/37:45 pmORD - PER
1 stop38h 25mEmirates
Deal found 2/21$1,803
This KAYAK deal was found by Cheapflights users on 2/21. 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.
Wed 10/2912:15 amPER - ORD
1 stop26h 45mCathay Pacific
Mon 11/32:40 pmORD - PER
1 stop42h 10mCathay Pacific
Deal found 2/21$2,067
This Jetabroad deal was found by Cheapflights users on 2/20. 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.
Thu 3/201:10 amPER - ORD
2 stops30h 06mSingapore Airlines
Fri 3/2811:44 amORD - PER
3 stops37h 56mSingapore Airlines
Deal found 2/20$3,020

Find flights from Waikiki to Chicago within your budget

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 February 23, 2025.

Fly from

Waikiki

Fly to

Chicago

Route

Depart

Return

Price

PerthChicago

PER - ORD

PERORD

Perth

Fri 3/21

8:00 am-11:59 pm

2 stops28h 59m

Chicago O'Hare Intl

Fri 3/28

8:20 pm-12:35 pm

2 stops27h 15m

$1,261

PerthChicago

PER - ORD

PERORD

Perth

Mon 4/7

8:50 pm-9:00 pm

2 stops61h 10m

Chicago O'Hare Intl

Sun 4/13

12:30 am-1:40 am

2 stops36h 10m

$1,331

PerthChicago

PER - ORD

PERORD

Perth

Sun 4/6

12:10 am-9:05 am

2 stops45h 55m

Chicago O'Hare Intl

Mon 4/14

12:05 pm-12:40 am

2 stops47h 35m

$1,507

PerthChicago

PER - ORD

PERORD

Perth

Mon 4/7

10:45 pm-5:39 pm

2 stops55h 54m

Chicago O'Hare Intl

Mon 4/14

7:20 pm-6:40 pm

1 stop34h 20m

$1,729

PerthChicago

PER - ORD

PERORD

Perth

Fri 4/18

6:00 am-3:45 pm

1 stop46h 45m

Chicago O'Hare Intl

Mon 4/28

8:35 pm-12:40 am

1 stop39h 05m

$1,829

PerthChicago

PER - ORD

PERORD

Perth

Fri 4/18

11:55 pm-7:30 pm

3 stops32h 35m

Chicago O'Hare Intl

Mon 4/28

2:05 pm-3:45 pm

3 stops36h 40m

$2,103

PerthChicago

PER - ORD

PERORD

Perth

Thu 3/20

12:15 am-2:00 pm

1 stop26h 45m

Chicago O'Hare Intl

Fri 3/28

3:40 pm-10:40 pm

1 stop42h 00m

$2,143

PerthChicago

PER - ORD

PERORD

Perth

Thu 3/20

1:10 am-6:16 pm

2 stops30h 06m

Chicago O'Hare Intl

Fri 3/28

11:44 am-2:40 pm

3 stops37h 56m

$3,020

PerthChicago

PER - ORD

PERORD

Perth

Mon 4/21

1:30 am-5:45 am

3 stops41h 15m

$673

PerthChicago

PER - ORD

PERORD

Perth

Wed 4/23

10:30 am-11:59 pm

2 stops26h 29m

$707

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 17 results
1
2

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.

Travel insights for flights from Waikiki to Chicago

Get recent, data-driven insights about flights from Waikiki to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 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 February 23, 2025.
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

ANA
8.4
Very good
836 reviews
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

Japan Airlines
8.3
Very good
1,440 reviews
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

Emirates
8.1
Very good
3,276 reviews
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

Singapore Airlines
8.1
Very good
1,296 reviews
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

Cathay Pacific
7.5
Good
822 reviews
ANA
8.4
Very good
836 reviews

Comfort

8.2

Food

7.6

Crew

8.7

Boarding

8.5

Entertainment

7.9

Overall

8.4

Reviews

1 / 20

10.0
Excellent

Anonymous,Feb 2025

MNL - HND

Great experience! Roomy economy leg room with foot rest, great crew and accommodations. Highly recommend!

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 Qantas Airways, which is currently one of the cheapest options available, starting at $707. Japan Airlines flights start at $1,063 while deals on United Airlines start at $1,148 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$1,184Average$1,411FlexibilityNo cancel feeOn-time71%
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