$730+ Cheap flights from Sydney (SYD) 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Oct 2 — Oct 91
Round-trip
1 adult, Economy
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Find cheap flights from Sydney to Chicago with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Sydney to Chicago
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Cheapest flights from Sydney to ChicagoExplore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:15 pm -
3 stops31h 01m
Sun 10/1810:26 am -
3 stops43h 59m
Deal found 8/28![Multiple Airlines logo]()
$1,067
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:15 pm -
3 stops31h 02m
Fri 10/2310:26 am -
3 stops34h 09m
Deal found 8/30![Multiple Airlines logo]()
$1,079
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:15 pm -
3 stops26h 30m
Sun 9/136:30 am -
3 stops38h 20m
Deal found 8/28![Multiple Airlines logo]()
$1,097
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Fri 10/96:50 pm -
1 stop27h 44m
Sat 10/178:01 pm -
1 stop43h 29m
Deal found 8/31![Multiple Airlines logo]()
$1,176
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:50 pm -
1 stop27h 44m
Fri 10/168:01 pm -
1 stop43h 29m
Deal found 8/28![Multiple Airlines logo]()
$1,205
This Aunt Betty deal was found by Cheapflights users on 9/2. 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 Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:50 am -
2 stops26h 55m
Mon 11/99:15 am -
2 stops30h 20m
Deal found 9/2![Air New Zealand logo]()
$1,262
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1212:15 pm -
2 stops34h 19m
Mon 10/198:01 pm -
1 stop43h 29m
Deal found 8/28![Multiple Airlines logo]()
$1,267
This Bravofly deal was found by Cheapflights users on 9/2. 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.
Wed 11/410:20 pm -
1 stop31h 35m
Mon 11/92:10 pm -
1 stop26h 25m
Deal found 9/2![Cathay Pacific logo]()
$1,270
This Bravofly deal was found by Cheapflights users on 9/1. 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.
Thu 10/2210:20 pm -
1 stop31h 35m
Mon 10/263:10 pm -
1 stop26h 25m
Deal found 9/1![Cathay Pacific logo]()
$1,297
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/319:30 am -
2 stops26h 01m
Sun 9/136:25 am -
2 stops33h 35m
Deal found 8/28![Multiple Airlines logo]()
$1,506
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:40 am -
2 stops23h 10m
Tue 1/129:30 am -
2 stops30h 00m
Deal found 8/31![Delta logo]()
$1,751
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:40 am -
2 stops22h 59m
Fri 12/411:28 am -
2 stops28h 02m
Deal found 8/28![Delta logo]()
$1,811
Best flights from Sydney to ChicagoDiscover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
This Etihad Airways deal was found by Cheapflights users on 8/28. 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 Etihad Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/114:40 pm -
2 stops37h 40m
Sun 10/188:25 pm -
1 stop42h 10m
Deal found 8/28![Multiple Airlines logo]()
$1,493
This Cathay Pacific deal was found by Cheapflights users on 8/28. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:15 pm -
1 stop38h 40m
Mon 11/92:10 pm -
1 stop37h 40m
Deal found 8/28![Cathay Pacific logo]()
$1,539
This Philippine Airlines deal was found by Cheapflights users on 8/30. 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 Philippine Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/2411:30 am -
1 stop46h 25m
Fri 2/510:45 pm -
1 stop42h 05m
Deal found 8/30![Philippine Airlines logo]()
$1,574
This Turkish Airlines deal was found by Cheapflights users on 8/30. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:35 pm -
2 stops53h 25m
Mon 2/18:15 pm -
2 stops54h 10m
Deal found 8/30![Turkish Airlines logo]()
$1,622
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:40 am -
2 stops23h 10m
Tue 1/129:30 am -
2 stops30h 00m
Deal found 8/31![Delta logo]()
$1,751
This Alaska Airlines deal was found by Cheapflights users on 8/30. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/209:40 pm -
2 stops25h 16m
Fri 2/56:57 pm -
2 stops31h 48m
Deal found 8/30![Multiple Airlines logo]()
$1,613
This Turkish Airlines deal was found by Cheapflights users on 8/31. 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 Turkish Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:35 pm -
2 stops54h 25m
Mon 11/98:15 pm -
2 stops54h 10m
Deal found 8/31![Turkish Airlines logo]()
$1,626
This Cathay Pacific deal was found by Cheapflights users on 8/28. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/99:20 am -
2 stops44h 35m
Fri 10/164:15 pm -
2 stops48h 00m
Deal found 8/28![Cathay Pacific logo]()
$1,701
This Delta deal was found by Cheapflights users on 8/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/291:35 pm -
1 stop25h 13m
Sat 1/167:30 am -
2 stops32h 00m
Deal found 8/30![Delta logo]()
$1,796
This Cathay Pacific deal was found by Cheapflights users on 8/29. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:25 am -
2 stops46h 30m
Sun 10/44:15 pm -
2 stops31h 15m
Deal found 8/29![Multiple Airlines logo]()
$1,660
This Cathay Pacific deal was found by Cheapflights users on 8/28. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/172:05 pm -
1 stop38h 50m
Wed 10/144:15 pm -
1 stop46h 55m
Deal found 8/28![Cathay Pacific logo]()
$1,735
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:40 am -
2 stops22h 59m
Fri 12/411:28 am -
2 stops28h 02m
Deal found 8/28![Delta logo]()
$1,811
This Cathay Pacific deal was found by Cheapflights users on 9/1. 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 9/227:40 am -
1 stop45h 15m
Wed 10/74:15 pm -
2 stops35h 45m
Deal found 9/1![Multiple Airlines logo]()
$1,746
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:15 am -
2 stops23h 45m
Sat 10/3111:33 am -
2 stops27h 57m
Deal found 8/29![Delta logo]()
$1,864
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/2510:15 am -
2 stops23h 45m
Thu 10/291:27 pm -
2 stops26h 03m
Deal found 9/1![Delta logo]()
$1,954
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1210:15 am -
2 stops22h 32m
Mon 10/191:27 pm -
2 stops26h 23m
Deal found 8/28![Delta logo]()
$1,973
This Delta deal was found by Cheapflights users on 8/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/710:15 am -
2 stops22h 32m
Fri 10/2312:27 pm -
2 stops27h 23m
Deal found 8/30![Delta logo]()
$2,020
This Delta deal was found by Cheapflights users on 8/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:15 am -
2 stops28h 18m
Sun 10/181:27 pm -
2 stops26h 23m
Deal found 8/28![Delta logo]()
$2,027
This Delta deal was found by Cheapflights users on 9/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1710:15 am -
2 stops22h 32m
Sat 10/241:27 pm -
2 stops26h 03m
Deal found 9/2![Delta logo]()
$2,071
This Delta deal was found by Cheapflights users on 8/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:15 am -
2 stops24h 18m
Wed 10/149:29 am -
2 stops30h 21m
Deal found 8/31![Delta logo]()
$2,074
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated September 2, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 8/31. 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 9/85:50 pm -
1 stop27h 27m
Thu 11/56:30 am -
2 stops30h 55m
Deal found 8/31![Multiple Airlines logo]()
$1,315
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/101:15 pm -
3 stops26h 30m
Sun 9/136:30 am -
3 stops38h 20m
Deal found 8/28![Multiple Airlines logo]()
$1,097
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/289:15 am -
2 stops28h 29m
Wed 10/149:29 am -
2 stops30h 21m
Deal found 8/29![Delta logo]()
$1,971
This Trip.com deal was found by Cheapflights users on 8/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/72:15 pm -
3 stops31h 02m
Fri 10/2310:26 am -
3 stops34h 09m
Deal found 8/30![Multiple Airlines logo]()
$1,079
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/82:15 pm -
2 stops32h 19m
Wed 10/218:01 pm -
1 stop43h 29m
Deal found 8/28![Multiple Airlines logo]()
$1,314
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Fri 10/96:50 pm -
1 stop27h 44m
Sat 10/178:01 pm -
1 stop43h 29m
Deal found 8/31![Multiple Airlines logo]()
$1,176
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:50 pm -
1 stop27h 44m
Fri 10/168:01 pm -
1 stop43h 29m
Deal found 8/28![Multiple Airlines logo]()
$1,205
This Trip.com deal was found by Cheapflights users on 8/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/112:15 pm -
3 stops31h 01m
Sun 10/1810:26 am -
3 stops43h 59m
Deal found 8/28![Multiple Airlines logo]()
$1,067
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/1212:15 pm -
2 stops34h 19m
Mon 10/198:01 pm -
1 stop43h 29m
Deal found 8/28![Multiple Airlines logo]()
$1,267
This Delta deal was found by Cheapflights users on 8/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1810:15 am -
2 stops23h 45m
Sat 10/3111:33 am -
2 stops27h 57m
Deal found 8/29![Delta logo]()
$1,864
This Bravofly deal was found by Cheapflights users on 9/1. 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.
Thu 10/2210:20 pm -
1 stop31h 35m
Mon 10/263:10 pm -
1 stop26h 25m
Deal found 9/1![Cathay Pacific logo]()
$1,297
This Delta deal was found by Cheapflights users on 9/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2210:15 am -
2 stops23h 45m
Mon 10/2612:27 pm -
2 stops27h 03m
Deal found 9/1![Delta logo]()
$1,954
One-way flights from Sydney to ChicagoSearch for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Expedia deal was found by Cheapflights users on 8/31. 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.
Mon 11/99:30 pm -
1 stop34h 30m
Deal found 8/31![Etihad Airways logo]()
$730
This oojo deal was found by Cheapflights users on 8/31. 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 11/79:30 pm -
1 stop51h 25m
Deal found 8/31![Etihad Airways logo]()
$739
This oojo deal was found by Cheapflights users on 8/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/268:50 pm -
1 stop33h 50m
Deal found 8/28![Etihad Airways logo]()
$740
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:30 pm -
1 stop51h 25m
Deal found 8/28![Etihad Airways logo]()
$744
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/59:30 pm -
1 stop51h 25m
Deal found 8/28![Etihad Airways logo]()
$745
This oojo deal was found by Cheapflights users on 8/28. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/44:50 pm -
1 stop32h 05m
Deal found 8/28![Etihad Airways logo]()
$755
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:15 pm -
3 stops48h 44m
Deal found 8/28![Multiple Airlines logo]()
$763
This Thrive Travel deal was found by Cheapflights users on 8/31. 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 Thrive Travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/99:10 am -
2 stops26h 06m
Deal found 8/31![Qantas Airways logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:00 pm -
3 stops32h 13m
Deal found 8/28![Multiple Airlines logo]()
$804
This Mytrip deal was found by Cheapflights users on 8/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/98:05 pm -
2 stops35h 32m
Deal found 8/31![Multiple Airlines logo]()
$805
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1111:15 am -
3 stops39h 44m
Deal found 8/30![Multiple Airlines logo]()
$1,056
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/188:20 pm -
3 stops51h 41m
Deal found 8/30![Multiple Airlines logo]()
$1,085
Find flight deals from Sydney to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 2, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,067 (Trip.com) |
One-way from | $730 (Expedia) |
Popular in | May |
Cheapest in | October |
Average price | $1,124 |
Cheapflights Fare Finder
Customize your flight search to find flights from Sydney 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 7,457,451 searches. Data last updated September 2, 2026.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sun 10/11
4:40 pm-2:20 pm
2 stops37h 40m
Chicago O'Hare Intl
Sun 10/18
8:25 pm-6:35 am
1 stop42h 10m
$1,493
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 11/5
3:15 pm-12:55 pm
1 stop38h 40m
Chicago O'Hare Intl
Mon 11/9
2:10 pm-8:50 pm
1 stop37h 40m
$1,539
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Tue 11/24
11:30 am-4:55 pm
1 stop46h 25m
Chicago O'Hare Intl
Fri 2/5
10:45 pm-9:50 am
1 stop42h 05m
$1,574
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Fri 11/20
9:40 pm-5:56 am
2 stops25h 16m
Chicago O'Hare Intl
Fri 2/5
6:57 pm-7:45 pm
2 stops31h 48m
$1,613
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Fri 11/20
9:35 pm-10:00 am
2 stops53h 25m
Chicago O'Hare Intl
Mon 2/1
8:15 pm-7:25 pm
2 stops54h 10m
$1,622
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 11/5
9:35 pm-11:00 am
2 stops54h 25m
Chicago O'Hare Intl
Mon 11/9
8:15 pm-7:25 pm
2 stops54h 10m
$1,626
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sun 9/27
6:25 am-1:55 pm
2 stops46h 30m
Chicago O'Hare Intl
Sun 10/4
4:15 pm-3:30 pm
2 stops31h 15m
$1,660
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Fri 10/9
9:20 am-1:55 pm
2 stops44h 35m
Chicago O'Hare Intl
Fri 10/16
4:15 pm-8:15 am
2 stops48h 00m
$1,701
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 9/17
2:05 pm-1:55 pm
1 stop38h 50m
Chicago O'Hare Intl
Wed 10/14
4:15 pm-7:10 am
1 stop46h 55m
$1,735
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Tue 9/22
7:40 am-1:55 pm
1 stop45h 15m
Chicago O'Hare Intl
Wed 10/7
4:15 pm-8:00 pm
2 stops35h 45m
$1,746
Showing 1-10 of 39 resultsSorted by cheapest first
Compare providers for flights from Sydney to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sydney to Chicago in September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Sydney-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sydney-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sydney-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Sydney-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sydney-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Sydney to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.
SYD-CHI
SYD-ORD
SYD-MDW
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 Sydney to Chicago
SYD-CHI
SYD-ORD
SYD-MDW
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, October is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,043). Flying from Sydney to Chicago in May is currently the most expensive (average of $1,432). 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 Sydney to Chicago?
Airfare is typical for this route at the moment.
Sydney to Chicago flights typically cost between $883 and $1,534 in October.The cheapest round-trip price found within the last 5 days was $1,067 on Multiple Airlines (Oct 11-Oct 18).
How far ahead should I book a flight from Sydney to Chicago?
The best time to book flights from Sydney to Chicago is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated September 2, 2026.
Read through reviews of airlines operating flights from Sydney to Chicago, such as United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Crew
8.1
Entertainment
7.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Sydney 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
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
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Sydney and Chicago flights
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Other flights from Sydney
Browse through other flights departing from Sydney. Flights are based on user searches made on Cheapflights and were last updated on September 2, 2026.
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Top airline flying from Sydney to Chicago
Discover the top airline that operate flights from Sydney 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 7,457,451 searches. Data last updated September 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$970 | Average$1,633 | FlexibilityNo cancel fee | On-time74% |