$845+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
PER — CHI
Jul 9 — Jul 161
Round-trip
1 adult, Economy
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Best
Last-minute
One-way
Cheapest flights from Waikiki to ChicagoExplore 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 June 9, 2026.
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 June 9, 2026.
This SmartFares deal was found by Cheapflights users on 6/6. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/16:15 am
PER
- ORD
2 stops26h 29m
Qantas Airways
Sat 8/153:21 pm
ORD
- PER
2 stops30h 54m
Qantas Airways
Deal found 6/6![Qantas Airways logo]()
$1,404
This lol.travel deal was found by Cheapflights users on 6/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:20 am
PER
- ORD
1 stop43h 00m
Cathay Pacific
Sun 7/264:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/7![Cathay Pacific logo]()
$1,581
This oojo deal was found by Cheapflights users on 6/7. 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 10/311:15 am
PER
- ORD
2 stops30h 22m
Multiple Airlines
Sat 11/218:42 pm
ORD
- PER
2 stops49h 53m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$1,597
This Bravofly deal was found by Cheapflights users on 6/5. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:10 am
PER
- ORD
1 stop27h 10m
Cathay Pacific
Tue 7/214:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/5![Cathay Pacific logo]()
$1,637
This Cathay Pacific deal was found by Cheapflights users on 6/5. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:25 am
PER
- ORD
1 stop26h 30m
Cathay Pacific
Sun 11/12:35 pm
ORD
- PER
1 stop42h 20m
Cathay Pacific
Deal found 6/5![Cathay Pacific logo]()
$1,701
This American Airlines deal was found by Cheapflights users on 6/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/911:45 pm
PER
- ORD
2 stops44h 57m
American Airlines
Sat 8/226:59 am
ORD
- PER
2 stops39h 16m
American Airlines
Deal found 6/8![American Airlines logo]()
$1,711
This oojo deal was found by Cheapflights users on 6/7. 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.
Sun 11/18:30 am
PER
- ORD
1 stop42h 25m
Cathay Pacific
Sat 11/212:35 pm
ORD
- PER
1 stop26h 20m
Cathay Pacific
Deal found 6/7![Cathay Pacific logo]()
$1,717
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1311:55 pm
PER
- ORD
2 stops44h 43m
American Airlines
Sun 7/2610:30 pm
ORD
- PER
2 stops47h 45m
American Airlines
Deal found 6/7![American Airlines logo]()
$1,724
Best flights from Waikiki to ChicagoDiscover carefully curated flight deals from Waikiki to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
Discover carefully curated flight deals from Waikiki to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 9, 2026.
This Bravofly deal was found by Cheapflights users on 6/9. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:20 am
PER
- ORD
1 stop43h 00m
Cathay Pacific
Sun 7/264:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/9![Cathay Pacific logo]()
$1,618
This Air Canada deal was found by Cheapflights users on 6/7. 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.
Sun 11/110:55 pm
PER
- ORD
3 stops34h 40m
Air Canada
Sat 11/213:40 pm
ORD
- PER
2 stops38h 30m
Air Canada
Deal found 6/7![Air Canada logo]()
$1,845
This Japan Airlines deal was found by Cheapflights users on 6/4. 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 Japan Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:30 am
PER
- ORD
2 stops35h 00m
Japan Airlines
Sun 11/110:20 am
ORD
- PER
2 stops47h 35m
Japan Airlines
Deal found 6/4![Japan Airlines logo]()
$1,970
This Qantas Airways deal was found by Cheapflights users on 6/6. 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.
Sat 8/110:30 am
PER
- ORD
3 stops27h 21m
Multiple Airlines
Sat 8/155:16 pm
ORD
- PER
2 stops28h 59m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$2,011
This Cathay Pacific deal was found by Cheapflights users on 6/5. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2712:25 am
PER
- ORD
1 stop26h 30m
Cathay Pacific
Sun 11/12:35 pm
ORD
- PER
1 stop42h 20m
Cathay Pacific
Deal found 6/5![Cathay Pacific logo]()
$1,701
This oojo deal was found by Cheapflights users on 6/7. 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.
Sun 11/18:30 am
PER
- ORD
1 stop42h 25m
Cathay Pacific
Sat 11/212:35 pm
ORD
- PER
1 stop26h 20m
Cathay Pacific
Deal found 6/7![Cathay Pacific logo]()
$1,717
This Cathay Pacific deal was found by Cheapflights users on 6/8. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:10 am
PER
- ORD
1 stop27h 10m
Multiple Airlines
Sat 8/228:29 pm
ORD
- PER
2 stops37h 11m
Multiple Airlines
Deal found 6/8![Multiple Airlines logo]()
$2,106
This Air Canada deal was found by Cheapflights users on 6/5. 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 7/145:15 pm
PER
- ORD
2 stops34h 21m
Air Canada
Tue 7/217:45 pm
ORD
- PER
2 stops31h 25m
Air Canada
Deal found 6/5![Air Canada logo]()
$2,111
This Cathay Pacific deal was found by Cheapflights users on 6/8. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:20 am
PER
- ORD
2 stops42h 44m
Cathay Pacific
Sat 7/184:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/8![Cathay Pacific logo]()
$2,155
Last-minute flights from Waikiki to ChicagoDiscover last-minute flight deals from Waikiki to Chicago. Data last updated June 9, 2026 and is based on user searches.
Discover last-minute flight deals from Waikiki to Chicago. Data last updated June 9, 2026 and is based on user searches.
This lol.travel deal was found by Cheapflights users on 6/7. 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 lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/138:20 am
PER
- ORD
1 stop43h 00m
Cathay Pacific
Sun 7/264:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/7![Cathay Pacific logo]()
$1,581
This Bravofly deal was found by Cheapflights users on 6/5. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:10 am
PER
- ORD
1 stop27h 10m
Cathay Pacific
Tue 7/214:00 pm
ORD
- PER
1 stop25h 50m
Cathay Pacific
Deal found 6/5![Cathay Pacific logo]()
$1,637
This American Airlines deal was found by Cheapflights users on 6/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1311:55 pm
PER
- ORD
2 stops44h 43m
American Airlines
Sun 7/2610:30 pm
ORD
- PER
2 stops47h 45m
American Airlines
Deal found 6/7![American Airlines logo]()
$1,724
This BYOjet deal was found by Cheapflights users on 6/9. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:15 pm
PER
- ORD
2 stops35h 45m
Multiple Airlines
Sun 7/262:30 pm
ORD
- PER
2 stops31h 50m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$1,965
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/1312:10 am
PER
- ORD
1 stop27h 10m
Multiple Airlines
Tue 7/214:00 pm
ORD
- PER
2 stops47h 45m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$2,034
This Air Canada deal was found by Cheapflights users on 6/5. 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 7/145:15 pm
PER
- ORD
2 stops34h 21m
Air Canada
Tue 7/217:45 pm
ORD
- PER
2 stops31h 25m
Air Canada
Deal found 6/5![Air Canada logo]()
$2,111
This Trip.com deal was found by Cheapflights users on 6/5. 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 7/208:20 am
PER
- ORD
1 stop43h 00m
Cathay Pacific
Mon 7/274:00 pm
ORD
- PER
1 stop41h 40m
Cathay Pacific
Deal found 6/5![Cathay Pacific logo]()
$1,746
This Booking.com deal was found by Cheapflights users on 6/5. 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.
Mon 7/2012:15 pm
PER
- ORD
2 stops35h 45m
Multiple Airlines
Mon 7/272:30 pm
ORD
- PER
2 stops31h 50m
Multiple Airlines
Deal found 6/5![Multiple Airlines logo]()
$2,039
One-way flights from Waikiki to ChicagoSearch for one-way flight options from Waikiki to Chicago. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
Search for one-way flight options from Waikiki to Chicago. Find affordable one-way fares based on user searches. Data last updated June 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:35 am
PER
- ORD
3 stops40h 55m
Multiple Airlines
Deal found 6/4![Multiple Airlines logo]()
$845
This BYOjet deal was found by Cheapflights users on 6/4. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1510:45 pm
PER
- ORD
1 stop29h 20m
Qatar Airways
Deal found 6/4![Qatar Airways logo]()
$1,062
This BYOjet deal was found by Cheapflights users on 6/4. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1412:10 am
PER
- ORD
1 stop27h 10m
Cathay Pacific
Deal found 6/4![Cathay Pacific logo]()
$3,174
Find flight deals from Waikiki to Chicago
Keep the following information in mind while searching for Waikiki to Chicago flight deals. Data was last updated June 9, 2026.
Round-trip from | $1,404 (SmartFares) |
|---|---|
One-way from | $845 (Kiwi.com) |
Popular in | April |
Cheapest in | May |
Average price | $1,846 |
Cheapflights Fare Finder
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 June 9, 2026.
Use the filters below to find and compare flights from Waikiki to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PerthChicago
PER - ORD
PERORD
Perth
Mon 7/13
8:20 am-2:20 pm
1 stop43h 00m
Chicago O'Hare Intl
Sun 7/26
4:00 pm-6:50 am
1 stop25h 50m
$1,618
PerthChicago
PER - ORD
PERORD
Perth
Tue 10/27
12:25 am-1:55 pm
1 stop26h 30m
Chicago O'Hare Intl
Sun 11/1
2:35 pm-10:55 pm
1 stop42h 20m
$1,701
PerthChicago
PER - ORD
PERORD
Perth
Sun 11/1
8:30 am-1:55 pm
1 stop42h 25m
Chicago O'Hare Intl
Sat 11/21
2:35 pm-6:55 am
1 stop26h 20m
$1,717
PerthChicago
PER - ORD
PERORD
Perth
Sun 11/1
10:55 pm-7:35 pm
3 stops34h 40m
Chicago O'Hare Intl
Sat 11/21
3:40 pm-8:10 pm
2 stops38h 30m
$1,845
PerthChicago
PER - ORD
PERORD
Perth
Wed 10/28
10:30 am-8:30 am
2 stops35h 00m
Chicago O'Hare Intl
Sun 11/1
10:20 am-11:55 pm
2 stops47h 35m
$1,970
Quickest round-trip
PerthChicago
PER - ORD
PERORD
Perth
Sat 8/1
10:30 am-12:51 am
3 stops27h 21m
Chicago O'Hare Intl
Sat 8/15
5:16 pm-11:15 am
2 stops28h 59m
$2,011
PerthChicago
PER - ORD
PERORD
Perth
Sat 8/8
12:10 am-2:20 pm
1 stop27h 10m
Chicago O'Hare Intl
Sat 8/22
8:29 pm-10:40 pm
2 stops37h 11m
$2,106
PerthChicago
PER - ORD
PERORD
Perth
Tue 7/14
5:15 pm-2:36 pm
2 stops34h 21m
Chicago O'Hare Intl
Tue 7/21
7:45 pm-4:10 pm
2 stops31h 25m
$2,111
PerthChicago
PER - ORD
PERORD
Perth
Sun 6/21
8:20 am-2:04 pm
2 stops42h 44m
Chicago O'Hare Intl
Sat 7/18
4:00 pm-6:50 am
1 stop25h 50m
$2,155
Cheapest one-way
PerthChicago
PER - ORD
PERORD
Perth
Tue 9/15
5:35 am-9:30 am
3 stops40h 55m
$845
Showing 1-10 of 12 resultsSorted by cheapest first
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.
PER-ORD
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 Waikiki to Chicago
WK1-CHI
PER-ORD
How much does it cost to fly round-trip from Waikiki to Chicago?
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.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Waikiki and Chicago flights
Browse other Waikiki and Chicago flight options. Last updated on June 9, 2026.
Popular flight searches
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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 June 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$973 | Average$976 | FlexibilityNo cancel fee | On-time79% |