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$628+ Cheap flights from Chicago (CHI) to Waikiki, Australia

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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PER
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Chicago to Waikiki

Keep the following information in mind while searching for Chicago to Waikiki flight deals. Data was last updated May 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$1,319
(Trip.com)

One-way from

$628
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$1,264
Provider with most accurate pricing for Chicago (CHI)-Perth flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Perth flights.
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From Chicago (CHI) to Waikiki
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One-way flight from Chicago (CHI) to Waikiki
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Highest demand for flights based on searches. 10% potential increase in price ($174 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 May 2025
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Find flight deals from Chicago to Waikiki

Cheapest flights from Chicago to Waikiki
Explore the most affordable flight options available from Chicago to Waikiki. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This Trip.com deal was found by Cheapflights users on 4/29. 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.
Wed 10/292:10 pmORD - PER
2 stops40h 40mMultiple Airlines
Sat 11/84:40 amPER - ORD
2 stops41h 35mMultiple Airlines
Deal found 4/29$1,261
This StudentUniverse deal was found by Cheapflights users on 4/29. 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 StudentUniverse is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/293:40 pmORD - PER
1 stop28h 55mCathay Pacific
Sat 11/812:15 amPER - ORD
1 stop26h 45mCathay Pacific
Deal found 4/29$1,418
This Gurufare deal was found by Cheapflights users on 4/29. 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.
Wed 10/294:35 pmORD - PER
2 stops35h 20mAir New Zealand
Sun 11/96:50 pmPER - ORD
2 stops39h 32mAir New Zealand
Deal found 4/29$1,518
This KAYAK deal was found by Cheapflights users on 4/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/229:00 pmORD - PER
2 stops37h 55mSingapore Airlines
Wed 12/31:50 pmPER - ORD
2 stops40h 20mSingapore Airlines
Deal found 4/30$1,622
This KAYAK deal was found by Cheapflights users on 4/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:45 pmORD - PER
2 stops30h 35mQantas Airways
Tue 12/210:40 pmPER - ORD
2 stops31h 20mQantas Airways
Deal found 4/30$1,732
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:00 pmORD - PER
2 stops31h 45mUnited Airlines
Sun 11/3011:45 pmPER - ORD
2 stops39h 26mUnited Airlines
Deal found 4/30$1,944
This Etihad Airways deal was found by Cheapflights users on 4/30. 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 Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:55 pmORD - PER
2 stops50h 55mEtihad Airways
Sun 11/3011:15 pmPER - ORD
2 stops47h 00mEtihad Airways
Deal found 4/30$1,956
This oojo deal was found by Cheapflights users on 4/29. 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.
Wed 10/297:55 pmORD - PER
1 stop27h 05mQatar Airways
Sun 11/910:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 4/29$2,005
This KAYAK deal was found by Cheapflights users on 4/30. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/258:10 pmORD - PER
2 stops35h 20mANA
Mon 12/19:55 pmPER - ORD
1 stop29h 55mANA
Deal found 4/30$2,115
This Air Canada deal was found by Cheapflights users on 4/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/252:00 pmORD - PER
3 stops35h 30mAir Canada
Sun 11/3010:55 pmPER - ORD
2 stops53h 44mAir Canada
Deal found 4/30$2,248

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Waikiki 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 May 1, 2025.
Use the filters below to find and compare flights from Chicago to Waikiki that are best for you.

Fly from

Chicago

Fly to

Waikiki

Route

Depart

Return

Price

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 5/3

12:30 am-1:20 am

2 stops35h 50m

Perth

Tue 5/6

5:10 am-11:36 am

3 stops43h 26m

$1,772

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Tue 6/10

5:51 pm-12:20 pm

2 stops29h 29m

Perth

Tue 6/17

11:55 pm-5:53 pm

2 stops30h 58m

$1,924

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 6/14

6:26 pm-2:40 pm

2 stops31h 14m

Perth

Sat 6/21

2:20 pm-8:25 pm

2 stops43h 05m

$2,140

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 5/4

7:20 pm-6:40 pm

1 stop34h 20m

Perth

Tue 5/6

10:45 pm-3:05 pm

1 stop29h 20m

$2,222

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 5/4

4:25 pm-4:00 pm

2 stops34h 35m

Perth

Tue 5/6

11:55 pm-2:42 pm

2 stops27h 47m

$2,338

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Tue 6/10

4:00 pm-10:40 pm

1 stop41h 40m

Perth

Mon 6/16

12:10 am-2:25 pm

1 stop27h 15m

$2,486

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Thu 6/12

1:01 pm-9:30 pm

3 stops43h 29m

Perth

Thu 6/19

11:55 pm-8:01 pm

2 stops33h 06m

$2,910

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 5/4

1:13 pm-2:40 pm

3 stops36h 27m

Perth

Tue 5/6

5:10 pm-9:54 pm

3 stops41h 44m

$3,329

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 6/14

8:35 pm-5:35 pm

1 stop32h 00m

Perth

Sat 6/21

6:00 am-3:45 pm

1 stop46h 45m

$3,480

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 6/14

7:05 pm-12:30 pm

2 stops28h 25m

Perth

Fri 6/20

1:10 am-12:10 pm

2 stops48h 00m

$4,371

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 15 results
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Best time to book a flight from Chicago to Waikiki

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

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

Currently, February is the cheapest month in which you can book a flight from Chicago to Waikiki (average of $1,448). Flying from Chicago to Waikiki in December is currently the most expensive (average of $2,172). 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.

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

Find hourly flight availability from Chicago to Waikiki. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Waikiki as you normally would.

Rainfall in Waikiki by month

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

In terms of precipitation, rainfall in Waikiki ranges from 0.0 - 6.7 inches per month. June is typically the wettest month, when rainfall can reach 6.7 in. January is typically the driest time to visit Waikiki when rainfall is around 0.0 in.

Temperature in Waikiki by month

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

If weather is an important factor for your trip to Waikiki, use this chart to help with planning. For those seeking warmer temperatures, January is the ideal time of year to visit, when temperatures reach an average of 75.2 F. Travelers looking to avoid the cold should look outside of July, when temperatures are typically at their lowest (around 53.6 F).

Reviews of airlines servicing Waikiki

Get insights into the airlines that provide service to Waikiki. 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 Waikiki. Reviews last updated May 1, 2025.
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
ANA
8.3
Very good
852 reviews
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Singapore Airlines
8.1
Very good
1,292 reviews
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Air New Zealand
8.0
Very good
472 reviews
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Cathay Pacific
7.5
Good
855 reviews
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.
Qantas Airways
7.5
Good
829 reviews
ANA
8.3
Very good
852 reviews

Overall

8.3

Entertainment

7.9

Crew

8.7

Boarding

8.5

Food

7.6

Comfort

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

SFO - HND

Don't bother with economy, it's so small!!! I'm a small person and I was cramped in the middle seat on a 11 hour flight. Not fun. Go for business or first class for such a long flight if you can or be prepared to have trouble moving when you stand up. Also be prepared to have trouble sleeping too. Crew was awesome though, they were helpful and provided excellent service.

Related info for your journey

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

    The cheapest airlines for a one-way flight from Chicago to Waikiki are Cathay Pacific ($968), Etihad Airways ($1,147), and Qantas Airways ($1,193).

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

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

  • How can I find direct flights from Chicago to Waikiki?

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

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

    Yes. Cheapflights offers flight deals from Chicago to Waikiki 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 Chicago to Waikiki?

    Currently, February is the cheapest month in which you can book a flight from Chicago to Waikiki (average of $1,448). Flying from Chicago to Waikiki in December is currently the most expensive (average of $2,172). 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

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Alternative routes for Chicago to Waikiki

See prices for flight routes from nearby airports that may be better suited for you.
St. Louis to Perth flights
O'Hare Intl to Perth flights
O'Hare Intl to Broome flights

Top 3 airlines flying from Chicago to Waikiki

Discover the top 3 airlines that operate flights from Chicago to Waikiki. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$1,191Average$1,522FlexibilityNo cancel feeOn-time74%
Cathay PacificCheapest$1,305Average$1,524FlexibilityNo cancel feeOn-time72%
Singapore AirlinesCheapest$1,421Average$1,706FlexibilityNo cancel feeOn-time81%

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