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Waikiki

$594+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PER
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$1,071
(Trip.com)

One-way from

$594
(Kiwi.com)

Popular in

September

Cheapest in

February

Average price

$2,520
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. 15% potential increase in price ($310 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($84 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 17, 2025.

This Trip.com deal was found by Cheapflights users on 9/15. 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.
Thu 10/303:35 pmORD - PER
2 stops47h 45mMultiple Airlines
Thu 11/65:35 amPER - ORD
2 stops45h 20mMultiple Airlines
Deal found 9/15$1,071
This Trip.com deal was found by Cheapflights users on 9/16. 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.
Fri 11/142:35 pmORD - PER
2 stops47h 45mMultiple Airlines
Sun 11/235:35 amPER - ORD
2 stops69h 20mMultiple Airlines
Deal found 9/16$1,092
This Trip.com deal was found by Cheapflights users on 9/16. 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 11/13:35 pmORD - PER
2 stops36h 00mMultiple Airlines
Sat 11/85:35 amPER - ORD
2 stops45h 20mMultiple Airlines
Deal found 9/16$1,243
This oojo deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:50 pmORD - PER
1 stop33h 55mQatar Airways
Wed 11/1210:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/15$1,304
This oojo deal was found by Cheapflights users on 9/15. 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.
Thu 10/307:50 pmORD - PER
1 stop33h 55mQatar Airways
Thu 11/610:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/15$1,310
This FlightHub deal was found by Cheapflights users on 9/16. 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.
Thu 11/136:50 pmORD - PER
1 stop27h 10mQatar Airways
Mon 11/2410:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,314
This oojo deal was found by Cheapflights users on 9/16. 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.
Fri 10/317:50 pmORD - PER
1 stop33h 55mQatar Airways
Fri 11/710:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,349
This FlightHub deal was found by Cheapflights users on 9/16. 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.
Thu 11/136:50 pmORD - PER
1 stop27h 10mQatar Airways
Sun 11/2310:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,353
This Gotogate deal was found by Cheapflights users on 9/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/66:50 pmORD - PER
1 stop27h 10mQatar Airways
Wed 11/1910:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,357
This FlightHub deal was found by Cheapflights users on 9/16. 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.
Fri 11/146:50 pmORD - PER
1 stop33h 55mQatar Airways
Mon 11/2410:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,358
This Ovago deal was found by Cheapflights users on 9/16. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:50 pmORD - PER
1 stop27h 10mQatar Airways
Mon 11/2410:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,359
This Ovago deal was found by Cheapflights users on 9/16. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/136:50 pmORD - PER
1 stop33h 55mQatar Airways
Fri 11/2110:45 pmPER - ORD
1 stop29h 45mQatar Airways
Deal found 9/16$1,363

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 September 17, 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

Thu 11/13

6:50 pm-12:00 pm

1 stop27h 10m

Perth

Thu 11/20

3:05 pm-2:30 pm

1 stop37h 25m

$1,435

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Thu 10/30

7:50 pm-6:45 pm

1 stop33h 55m

Perth

Thu 11/6

4:15 pm-2:30 pm

2 stops36h 15m

$1,441

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Wed 11/12

6:50 pm-12:00 pm

1 stop27h 10m

Perth

Sat 11/22

10:45 pm-2:30 pm

1 stop29h 45m

$1,475

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 11/16

6:50 pm-1:25 am

2 stops40h 35m

Perth

Mon 11/24

10:45 pm-2:30 pm

1 stop29h 45m

$1,551

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Wed 11/12

6:50 pm-1:25 am

2 stops40h 35m

Perth

Mon 11/24

10:45 pm-2:30 pm

1 stop29h 45m

$1,551

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Thu 11/13

2:35 pm-6:55 am

1 stop26h 20m

Perth

Wed 11/19

12:25 am-12:55 pm

1 stop26h 30m

$1,559

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sun 12/7

4:04 pm-12:00 pm

2 stops29h 56m

Perth

Wed 1/28

10:45 pm-2:30 pm

1 stop29h 45m

$1,576

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Sat 11/15

6:50 pm-1:25 am

2 stops40h 35m

Perth

Mon 11/24

10:45 pm-2:30 pm

1 stop29h 45m

$1,591

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Wed 11/12

6:50 pm-1:25 am

2 stops40h 35m

Perth

Sun 11/23

10:45 pm-2:30 pm

1 stop29h 45m

$1,591

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

Fri 11/14

6:50 pm-1:25 am

2 stops40h 35m

Perth

Mon 11/24

10:45 pm-2:30 pm

1 stop29h 45m

$1,591

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 21 results
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2
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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 $1,436). Flying from Chicago to Waikiki in December is currently the most expensive (average of $2,094). 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 September 17, 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 September 17, 2025.
Read through reviews of airlines operating flights from Chicago to Waikiki, such as Cathay Pacific and Qantas Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Cathay Pacific
7.6
Good
998 reviews

Overall

7.6

Boarding

7.9

Crew

8.1

Comfort

7.6

Food

7.3

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

anish,Aug 2025

YYZ - HKG

Overall journey was good. The economy seats on this airbus a350 was the worst . Too narrow and no underthigh support . My next journey from Hongkong to kathmandu was better as the economy seats on airbus a330 was a lot better than on this plane . Cathy should make a note on this . The long haul flights should have at least comfy seats compared to short flights from Hongkong to ktm
Cathay Pacific
7.6
Good
998 reviews
Cathay Pacific
7.6
Good
998 reviews

Overall

7.6

Boarding

7.9

Crew

8.1

Comfort

7.6

Food

7.3

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

anish,Aug 2025

YYZ - HKG

Overall journey was good. The economy seats on this airbus a350 was the worst . Too narrow and no underthigh support . My next journey from Hongkong to kathmandu was better as the economy seats on airbus a330 was a lot better than on this plane . Cathy should make a note on this . The long haul flights should have at least comfy seats compared to short flights from Hongkong to ktm
Qantas Airways
7.5
Good
907 reviews
Cathay Pacific
7.6
Good
998 reviews

Overall

7.6

Boarding

7.9

Crew

8.1

Comfort

7.6

Food

7.3

Entertainment

7.8

Reviews

1 / 20
10.0
Excellent

anish,Aug 2025

YYZ - HKG

Overall journey was good. The economy seats on this airbus a350 was the worst . Too narrow and no underthigh support . My next journey from Hongkong to kathmandu was better as the economy seats on airbus a330 was a lot better than on this plane . Cathy should make a note on this . The long haul flights should have at least comfy seats compared to short flights from Hongkong to ktm

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.

  • How long is the flight from Chicago to Waikiki?

    Qatar Airways can get you from Chicago to Waikiki in just under 27h 10m. Your travel time can differ by up to . There are 10947 mi between Chicago and Waikiki.

  • 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 $1,436). Flying from Chicago to Waikiki in December is currently the most expensive (average of $2,094). 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 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$1,191Average$1,522FlexibilityNo cancel feeOn-time74%
Qatar AirwaysCheapest$1,229Average$1,331FlexibilityNo cancel feeOn-time68%
Cathay PacificCheapest$1,468Average$2,048FlexibilityNo cancel feeOn-time72%

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