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Waikiki

$564+ 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 2/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — PER
feb. 28 — mar. 71
sáb. 2/28
sáb. 3/7
1 adult, Economy
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Cheap 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 enero 29, 2026.

This Trip.com deal was found by Cheapflights users on 1/27. 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.
lun. 10/127:20 pm
ORD
-
PER
2 stops34h 15m
Multiple Airlines
vie. 10/238:30 pm
PER
-
ORD
2 stops56h 00m
Multiple Airlines
Deal found 1/27$1,467
This FlightHub deal was found by Cheapflights users on 1/27. 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.
jue. 2/263:35 pm
ORD
-
PER
2 stops38h 35m
Multiple Airlines
dom. 3/810:30 pm
PER
-
ORD
2 stops34h 30m
Multiple Airlines
Deal found 1/27$1,538
This FlightHub deal was found by Cheapflights users on 1/27. 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.
jue. 3/53:35 pm
ORD
-
PER
2 stops34h 20m
Multiple Airlines
sáb. 3/144:45 pm
PER
-
ORD
2 stops34h 56m
Multiple Airlines
Deal found 1/27$1,544
This oojo deal was found by Cheapflights users on 1/27. 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.
vie. 3/63:54 pm
ORD
-
PER
2 stops47h 31m
Multiple Airlines
dom. 3/151:50 pm
PER
-
ORD
3 stops46h 06m
Multiple Airlines
Deal found 1/27$1,563
This Expedia deal was found by Cheapflights users on 1/28. 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.
vie. 2/271:24 pm
ORD
-
PER
2 stops38h 51m
Qantas Airways
vie. 3/610:55 pm
PER
-
ORD
2 stops32h 51m
Qantas Airways
Deal found 1/28$1,586
This oojo deal was found by Cheapflights users on 1/27. 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.
jue. 3/55:29 pm
ORD
-
PER
2 stops45h 56m
Multiple Airlines
dom. 3/151:50 pm
PER
-
ORD
3 stops46h 06m
Multiple Airlines
Deal found 1/27$1,609
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/123:40 pm
ORD
-
PER
2 stops39h 50m
Air Canada
vie. 10/2310:55 pm
PER
-
ORD
3 stops36h 04m
Air Canada
Deal found 1/28$1,619
This Expedia deal was found by Cheapflights users on 1/28. 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.
dom. 3/157:29 pm
ORD
-
PER
2 stops29h 21m
Multiple Airlines
dom. 3/2211:35 am
PER
-
ORD
2 stops31h 02m
Multiple Airlines
Deal found 1/28$1,632
This oojo deal was found by Cheapflights users on 1/27. 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.
sáb. 3/142:08 pm
ORD
-
PER
2 stops32h 57m
Qantas Airways
dom. 3/2210:40 pm
PER
-
ORD
2 stops38h 07m
Qantas Airways
Deal found 1/27$1,648
This Air Canada deal was found by Cheapflights users on 1/28. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/23:40 pm
ORD
-
PER
2 stops38h 40m
Air Canada
vie. 11/610:30 pm
PER
-
ORD
2 stops30h 11m
Air Canada
Deal found 1/28$1,651

Find flight deals from Chicago to Waikiki

Keep the following information in mind while searching for Chicago to Waikiki flight deals. Data was last updated enero 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$1,538
(FlightHub)

One-way from

$564
(Kiwi.com)

Popular in

September

Cheapest in

March

Average price

$1,732
Provider with most accurate pricing for Chicago (CHI)-Perth flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Perth flights.
Search Deals
From Chicago (CHI) to Waikiki
Search Deals
One-way flight from Chicago (CHI) to Waikiki
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($251 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($81 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 enero 29, 2026.
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

jue. 2/26

3:35 pm-8:10 pm

2 stops38h 35m

Perth

dom. 3/8

10:30 pm-8:00 pm

2 stops34h 30m

$1,538

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

jue. 3/5

3:35 pm-3:55 pm

2 stops34h 20m

Perth

sáb. 3/14

4:45 pm-2:41 pm

2 stops34h 56m

$1,544

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

sáb. 3/14

3:54 pm-5:25 am

2 stops48h 31m

Perth

dom. 3/22

5:05 pm-10:56 pm

3 stops42h 51m

$1,563

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

vie. 2/27

1:24 pm-6:15 pm

2 stops38h 51m

Perth

vie. 3/6

10:55 pm-5:46 pm

2 stops32h 51m

$1,586

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

jue. 3/5

1:10 pm-7:35 pm

2 stops40h 25m

Perth

dom. 3/15

10:30 am-8:35 am

2 stops35h 05m

$1,629

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

dom. 3/15

7:29 pm-1:50 pm

2 stops29h 21m

Perth

dom. 3/22

11:35 am-5:37 am

2 stops31h 02m

$1,632

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

sáb. 3/14

2:08 pm-12:05 pm

2 stops32h 57m

Perth

dom. 3/22

10:40 pm-11:47 pm

2 stops38h 07m

$1,648

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

dom. 3/15

1:12 pm-2:30 pm

3 stops36h 18m

Perth

dom. 3/22

10:30 pm-8:00 pm

2 stops34h 30m

$1,658

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

dom. 2/15

1:24 pm-12:05 pm

2 stops32h 41m

Perth

jue. 3/5

5:55 am-11:47 pm

2 stops31h 52m

$1,661

ChicagoPerth

ORD - PER

ORDPER

Chicago O'Hare Intl

vie. 2/27

6:50 pm-11:55 am

1 stop27h 05m

Perth

vie. 3/6

10:45 pm-2:30 pm

1 stop29h 45m

$1,664

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 19 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, May is the cheapest month in which you can book a flight from Chicago to Waikiki (average of $1,231). Flying from Chicago to Waikiki in July is currently the most expensive (average of $1,615). 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.

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 enero 29, 2026.
Read through reviews of airlines operating flights from Chicago to Waikiki, such as Qantas Airways. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Qantas Airways
7.5
Good
981 reviews

Comfort

7.5

Crew

8.2

Boarding

7.7

Entertainment

7.2

Overall

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.
Qantas Airways
7.5
Good
981 reviews
Qantas Airways
7.5
Good
981 reviews

Comfort

7.5

Crew

8.2

Boarding

7.7

Entertainment

7.2

Overall

7.5

Food

7.0

Reviews

1 / 20
10.0
Excellent

Carol,Oct 2025

ADL - MEL

Smooth flight, good onboard staff who were very caring when I didn’t feel very well.

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?

    Qantas Airways can get you from Chicago to Waikiki in just under 38h 51m. 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, May is the cheapest month in which you can book a flight from Chicago to Waikiki (average of $1,231). Flying from Chicago to Waikiki in July is currently the most expensive (average of $1,615). 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.
O'Hare Intl to Perth flights
St. Louis 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 enero 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$1,191Average$1,779FlexibilityNo cancel feeOn-time74%
Qatar AirwaysCheapest$1,229Average$2,092FlexibilityNo cancel feeOn-time68%
Cathay PacificCheapest$1,418Average$1,773FlexibilityNo cancel feeOn-time72%

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