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Waikiki

$509+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PER
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$1,045
(Trip.com)

One-way from

$509
(Kiwi.com)

Popular in

September

Cheapest in

February

Average price

$2,097
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. 14% potential increase in price ($284 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($77 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 25, 2025.

This Trip.com deal was found by Cheapflights users on 7/22. 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.
Tue 9/24:00 pmORD - PER
2 stops38h 40mMultiple Airlines
Tue 9/97:50 amPER - ORD
2 stops43h 35mMultiple Airlines
Deal found 7/22$1,045
This oojo deal was found by Cheapflights users on 7/23. 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 9/17:20 pmORD - PER
1 stop27h 35mQatar Airways
Mon 9/1510:45 pmPER - ORD
1 stop29h 20mQatar Airways
Deal found 7/23$1,329
This oojo deal was found by Cheapflights users on 7/23. 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.
Sat 9/66:00 amORD - PER
2 stops36h 25mPhilippine Airlines
Sat 9/138:45 amPER - ORD
2 stops40h 30mPhilippine Airlines
Deal found 7/23$1,410
This Gurufare deal was found by Cheapflights users on 7/23. 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.
Mon 9/14:00 pmORD - PER
1 stop26h 45mCathay Pacific
Sun 9/1412:10 amPER - ORD
1 stop27h 15mCathay Pacific
Deal found 7/23$1,515
This Air Canada deal was found by Cheapflights users on 7/23. 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.
Tue 9/163:40 pmORD - PER
2 stops40h 50mAir Canada
Tue 9/303:30 pmPER - ORD
3 stops40h 59mAir Canada
Deal found 7/23$1,693

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 July 25, 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

Tue 9/2

4:00 pm-7:40 pm

2 stops38h 40m

Perth

Tue 9/9

7:50 am-2:25 pm

2 stops43h 35m

$1,045

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Mon 9/1

7:20 pm-11:55 am

1 stop27h 35m

Perth

Mon 9/15

10:45 pm-3:05 pm

1 stop29h 20m

$1,329

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 9/6

6:00 am-7:25 am

2 stops36h 25m

Perth

Sat 9/13

8:45 am-12:15 pm

2 stops40h 30m

$1,410

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Mon 9/1

4:00 pm-7:45 am

1 stop26h 45m

Perth

Sun 9/14

12:10 am-2:25 pm

1 stop27h 15m

$1,515

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Tue 9/16

3:40 pm-9:30 pm

2 stops40h 50m

Perth

Tue 9/30

3:30 pm-7:29 pm

3 stops40h 59m

$1,693

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Mon 8/18

12:15 pm-1:20 am

2 stops48h 05m

$509

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Mon 8/18

7:20 pm-11:55 am

1 stop27h 35m

$719

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

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 $1,455). 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 July 25, 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.

How much does it cost to fly round-trip from Chicago to Waikiki?

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 July 25, 2025.
Read through reviews of airlines operating flights from Chicago to Waikiki, such as Cathay Pacific, Qatar Airways, and Philippine Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Cathay Pacific
7.6
Good
943 reviews

Overall

7.6

Boarding

7.9

Food

7.3

Entertainment

7.8

Crew

8.1

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

Douglas,Jun 2025

MNL - HKG

Flight attendant was very helpful in finding something simple to eat as opposed to a full meal. I appreciated her efforts to make it a comfortable flight.
Cathay Pacific
7.6
Good
943 reviews
Cathay Pacific
7.6
Good
943 reviews

Overall

7.6

Boarding

7.9

Food

7.3

Entertainment

7.8

Crew

8.1

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

Douglas,Jun 2025

MNL - HKG

Flight attendant was very helpful in finding something simple to eat as opposed to a full meal. I appreciated her efforts to make it a comfortable flight.
Qatar Airways
7.4
Good
3,611 reviews
Cathay Pacific
7.6
Good
943 reviews

Overall

7.6

Boarding

7.9

Food

7.3

Entertainment

7.8

Crew

8.1

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

Douglas,Jun 2025

MNL - HKG

Flight attendant was very helpful in finding something simple to eat as opposed to a full meal. I appreciated her efforts to make it a comfortable flight.
Philippine Airlines
7.2
Good
894 reviews
Cathay Pacific
7.6
Good
943 reviews

Overall

7.6

Boarding

7.9

Food

7.3

Entertainment

7.8

Crew

8.1

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

Douglas,Jun 2025

MNL - HKG

Flight attendant was very helpful in finding something simple to eat as opposed to a full meal. I appreciated her efforts to make it a comfortable flight.
Air Canada
7.1
Good
9,788 reviews
Cathay Pacific
7.6
Good
943 reviews

Overall

7.6

Boarding

7.9

Food

7.3

Entertainment

7.8

Crew

8.1

Comfort

7.6

Reviews

1 / 20
10.0
Excellent

Douglas,Jun 2025

MNL - HKG

Flight attendant was very helpful in finding something simple to eat as opposed to a full meal. I appreciated her efforts to make it a comfortable flight.

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.

  • 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 $1,455). 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.
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Top 2 airlines flying from Chicago to Waikiki

Discover the top 2 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 July 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$1,191Average$1,522FlexibilityNo cancel feeOn-time74%
Cathay PacificCheapest$1,470Average$1,555FlexibilityNo cancel feeOn-time72%

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