$498+ 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 9/4. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Sep 9 — Sep 161
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 August 10, 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 August 10, 2026.
This SmartFares deal was found by Cheapflights users on 8/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:25 am -
2 stops24h 29m
Sat 9/125:50 pm -
2 stops30h 55m
Deal found 8/7![Qantas Airways logo]()
$1,190
This SmartFares deal was found by Cheapflights users on 8/6. 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.
Tue 11/1010:20 pm -
1 stop31h 35m
Wed 11/252:35 pm -
1 stop26h 00m
Deal found 8/6![Cathay Pacific logo]()
$1,197
This SmartFares deal was found by Cheapflights users on 8/6. 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.
Mon 11/210:20 pm -
1 stop31h 35m
Tue 11/172:35 pm -
1 stop47h 40m
Deal found 8/6![Cathay Pacific logo]()
$1,198
This SmartFares deal was found by Cheapflights users on 8/6. 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.
Sun 11/110:20 pm -
1 stop31h 35m
Wed 11/182:35 pm -
1 stop26h 00m
Deal found 8/6![Cathay Pacific logo]()
$1,231
This BYOjet deal was found by Cheapflights users on 8/7. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:55 am -
2 stops28h 54m
Tue 11/172:22 pm -
2 stops27h 13m
Deal found 8/7![Air New Zealand logo]()
$1,232
This BYOjet deal was found by Cheapflights users on 8/5. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:55 am -
2 stops30h 04m
Tue 9/222:35 pm -
2 stops27h 10m
Deal found 8/5![Air New Zealand logo]()
$1,233
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/211:50 am -
2 stops26h 46m
Tue 11/172:22 pm -
2 stops25h 13m
Deal found 8/6![Air New Zealand logo]()
$1,237
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:40 am -
1 stop45h 40m
Fri 9/184:15 pm -
1 stop36h 55m
Deal found 8/6![Cathay Pacific logo]()
$1,248
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:30 am -
2 stops30h 05m
Wed 11/251:00 pm -
2 stops26h 35m
Deal found 8/6![Air New Zealand logo]()
$1,255
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:55 am -
2 stops28h 04m
Fri 9/115:53 pm -
2 stops23h 52m
Deal found 8/6![Air New Zealand logo]()
$1,284
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/107:30 am -
2 stops30h 05m
Thu 11/262:22 pm -
2 stops25h 13m
Deal found 8/6![Air New Zealand logo]()
$1,306
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:50 pm -
1 stop27h 09m
Mon 9/146:00 am -
2 stops34h 30m
Deal found 8/9![Multiple Airlines logo]()
$1,344
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 August 10, 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 August 10, 2026.
This Cathay Pacific deal was found by Cheapflights users on 8/5. 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 9/86:55 pm -
2 stops34h 25m
Fri 9/184:15 pm -
1 stop46h 55m
Deal found 8/5![Multiple Airlines logo]()
$1,493
This Cathay Pacific deal was found by Cheapflights users on 8/9. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/12:05 pm -
1 stop38h 50m
Fri 10/94:15 pm -
2 stops47h 30m
Deal found 8/9![Cathay Pacific logo]()
$1,590
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/310:40 am -
2 stops23h 07m
Tue 11/1712:30 pm -
2 stops27h 00m
Deal found 8/7![Delta logo]()
$1,722
This Cathay Pacific deal was found by Cheapflights users on 8/6. 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 Cathay Pacific is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:40 am -
1 stop45h 40m
Thu 9/174:15 pm -
2 stops32h 15m
Deal found 8/6![Multiple Airlines logo]()
$1,541
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:40 am -
2 stops23h 07m
Tue 11/1711:28 am -
2 stops28h 02m
Deal found 8/6![Delta logo]()
$1,725
This Alaska Airlines deal was found by Cheapflights users on 8/7. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/39:40 pm -
3 stops25h 00m
Tue 11/172:07 pm -
2 stops36h 38m
Deal found 8/7![Multiple Airlines logo]()
$1,620
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:40 am -
2 stops24h 24m
Tue 11/241:22 pm -
2 stops26h 08m
Deal found 8/6![Delta logo]()
$1,725
This Qantas Airways deal was found by Cheapflights users on 8/8. 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 Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:00 pm -
2 stops21h 52m
Sun 9/135:50 pm -
1 stop22h 15m
Deal found 8/8![Multiple Airlines logo]()
$1,647
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1010:40 am -
2 stops22h 59m
Thu 11/2612:30 pm -
2 stops27h 00m
Deal found 8/6![Delta logo]()
$1,751
This Cathay Pacific deal was found by Cheapflights users on 8/10. 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 10/17:45 pm -
2 stops33h 10m
Fri 10/94:15 pm -
2 stops47h 30m
Deal found 8/10![Multiple Airlines logo]()
$1,657
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:15 am -
2 stops24h 04m
Tue 9/222:00 pm -
2 stops25h 50m
Deal found 8/5![Delta logo]()
$1,931
This Mytrip deal was found by Cheapflights users on 8/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:35 pm -
2 stops33h 08m
Wed 9/3011:05 am -
2 stops29h 15m
Deal found 8/9![Multiple Airlines logo]()
$1,759
This Delta deal was found by Cheapflights users on 8/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:15 am -
2 stops24h 04m
Tue 9/291:19 pm -
2 stops26h 31m
Deal found 8/8![Delta logo]()
$1,936
This Delta deal was found by Cheapflights users on 8/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:15 am -
2 stops24h 04m
Wed 9/302:00 pm -
2 stops25h 50m
Deal found 8/9![Delta logo]()
$1,942
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:15 am -
2 stops24h 04m
Fri 9/181:19 pm -
2 stops26h 31m
Deal found 8/7![Delta logo]()
$1,970
This Delta deal was found by Cheapflights users on 8/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:15 am -
2 stops24h 04m
Fri 9/181:19 pm -
2 stops26h 31m
Deal found 8/6![Delta logo]()
$1,973
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/199:15 am -
2 stops28h 29m
Sun 9/279:29 am -
2 stops30h 21m
Deal found 8/5![Delta logo]()
$2,034
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated August 10, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated August 10, 2026 and is based on user searches.
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:55 am -
2 stops28h 04m
Fri 9/115:53 pm -
2 stops23h 52m
Deal found 8/6![Air New Zealand logo]()
$1,284
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:50 pm -
1 stop27h 09m
Fri 9/116:00 am -
2 stops34h 30m
Deal found 8/6![Multiple Airlines logo]()
$1,360
This SmartFares deal was found by Cheapflights users on 8/7. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:25 am -
2 stops24h 29m
Sat 9/125:50 pm -
2 stops30h 55m
Deal found 8/7![Qantas Airways logo]()
$1,190
This Kiwi.com deal was found by Cheapflights users on 8/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:50 pm -
1 stop27h 09m
Mon 9/146:00 am -
2 stops34h 30m
Deal found 8/9![Multiple Airlines logo]()
$1,344
This BYOjet deal was found by Cheapflights users on 8/9. 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.
Sun 8/307:50 am -
2 stops32h 09m
Mon 9/145:53 pm -
2 stops23h 52m
Deal found 8/9![Air New Zealand logo]()
$1,372
This BYOjet deal was found by Cheapflights users on 8/5. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/89:55 am -
2 stops30h 04m
Tue 9/222:35 pm -
2 stops27h 10m
Deal found 8/5![Air New Zealand logo]()
$1,233
This Kiwi.com deal was found by Cheapflights users on 8/5. 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.
Tue 9/81:15 pm -
2 stops32h 02m
Tue 9/225:45 pm -
1 stop24h 40m
Deal found 8/5![Multiple Airlines logo]()
$1,359
This SmartFares deal was found by Cheapflights users on 8/5. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/810:10 am -
1 stop43h 10m
Fri 9/184:15 pm -
1 stop36h 55m
Deal found 8/5![Cathay Pacific logo]()
$1,373
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:40 am -
1 stop45h 40m
Fri 9/184:15 pm -
1 stop36h 55m
Deal found 8/6![Cathay Pacific logo]()
$1,248
This Jetabroad deal was found by Cheapflights users on 8/6. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/911:55 am -
2 stops24h 35m
Thu 9/102:16 pm -
2 stops27h 29m
Deal found 8/6![Air New Zealand logo]()
$1,358
This Bravofly deal was found by Cheapflights users on 8/6. 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 Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:40 am -
1 stop45h 40m
Thu 9/174:15 pm -
1 stop36h 55m
Deal found 8/6![Cathay Pacific logo]()
$1,345
This BYOjet deal was found by Cheapflights users on 8/6. 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 BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1011:55 am -
2 stops28h 04m
Thu 9/172:16 pm -
2 stops27h 29m
Deal found 8/6![Air New Zealand logo]()
$1,353
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 August 10, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated August 10, 2026.
This Trip.com deal was found by Cheapflights users on 8/8. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:15 pm -
2 stops32h 02m
Deal found 8/8![Multiple Airlines logo]()
$498
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/102:00 pm -
3 stops45h 29m
Deal found 8/6![Multiple Airlines logo]()
$512
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:05 am -
2 stops38h 54m
Deal found 8/8![Multiple Airlines logo]()
$534
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:00 pm -
3 stops32h 40m
Deal found 8/7![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/22:00 pm -
3 stops37h 58m
Deal found 8/7![Multiple Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 8/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/102:00 pm -
3 stops37h 58m
Deal found 8/6![Multiple Airlines logo]()
$591
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:20 am -
3 stops47h 40m
Deal found 8/8![Multiple Airlines logo]()
$598
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/41:15 pm -
3 stops36h 35m
Deal found 8/8![Multiple Airlines logo]()
$627
This SmartFares deal was found by Cheapflights users on 8/6. 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.
Tue 11/1010:20 pm -
1 stop31h 35m
Deal found 8/6![Cathay Pacific logo]()
$650
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am -
3 stops49h 00m
Deal found 8/8![Multiple Airlines logo]()
$684
This Kiwi.com deal was found by Cheapflights users on 8/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am -
3 stops29h 31m
Deal found 8/8![Multiple Airlines logo]()
$689
This Bravofly deal was found by Cheapflights users on 8/9. 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.
Thu 9/248:50 pm -
1 stop33h 50m
Deal found 8/9![Etihad Airways logo]()
$692
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 August 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $969 (Air Canada) |
One-way from | $498 (Trip.com) |
Popular in | July |
Cheapest in | August |
Average price | $1,080 |
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 2,558,603 searches. Data last updated August 10, 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
Tue 9/8
6:55 pm-2:20 pm
2 stops34h 25m
Chicago O'Hare Intl
Fri 9/18
4:15 pm-6:10 am
1 stop46h 55m
$1,493
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 9/10
7:40 am-2:20 pm
1 stop45h 40m
Chicago O'Hare Intl
Thu 9/17
4:15 pm-3:30 pm
2 stops32h 15m
$1,541
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 10/1
2:05 pm-1:55 pm
1 stop38h 50m
Chicago O'Hare Intl
Fri 10/9
4:15 pm-7:45 am
2 stops47h 30m
$1,590
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Tue 11/3
9:40 pm-5:40 am
3 stops25h 00m
Chicago O'Hare Intl
Tue 11/17
2:07 pm-7:45 pm
2 stops36h 38m
$1,620
Quickest round-trip
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Sat 8/29
12:00 pm-6:52 pm
2 stops21h 52m
Chicago O'Hare Intl
Sun 9/13
5:50 pm-7:05 am
1 stop22h 15m
$1,647
SydneyChicago
SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl
SYDORD
Sydney Kingsford Smith
Thu 10/1
7:45 pm-1:55 pm
2 stops33h 10m
Chicago O'Hare Intl
Fri 10/9
4:15 pm-7:45 am
2 stops47h 30m
$1,657
SydneyChicago
SYD Sydney Kingsford Smith - MDW Chicago Midway
SYDMDW
Sydney Kingsford Smith
Tue 11/3
10:40 am-4:47 pm
2 stops23h 07m
Chicago Midway
Tue 11/17
12:30 pm-8:30 am
2 stops27h 00m
$1,722
SydneyChicago
SYD Sydney Kingsford Smith - MDW Chicago Midway
SYDMDW
Sydney Kingsford Smith
Mon 11/2
10:40 am-4:47 pm
2 stops23h 07m
Chicago Midway
Tue 11/17
11:28 am-8:30 am
2 stops28h 02m
$1,725
SydneyChicago
SYD Sydney Kingsford Smith - MDW Chicago Midway
SYDMDW
Sydney Kingsford Smith
Tue 11/10
10:40 am-6:04 pm
2 stops24h 24m
Chicago Midway
Tue 11/24
1:22 pm-8:30 am
2 stops26h 08m
$1,725
SydneyChicago
SYD Sydney Kingsford Smith - MDW Chicago Midway
SYDMDW
Sydney Kingsford Smith
Tue 11/10
10:40 am-4:39 pm
2 stops22h 59m
Chicago Midway
Thu 11/26
12:30 pm-8:30 am
2 stops27h 00m
$1,751
Showing 1-10 of 34 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 August.
| 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, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $1,014). Flying from Sydney to Chicago in July is currently the most expensive (average of $1,401). 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 $948 and $1,331 in August.The cheapest round-trip price found within the last 5 days was $1,190 on Qantas Airways (Aug 28-Sep 12).
How far ahead should I book a flight from Sydney to Chicago?
The best time to book flights from Sydney to Chicago is 10 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 August 10, 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.
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - ORD
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Oct 2025
YUL - 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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Alternative routes for Sydney to Chicago
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 10, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Sydney to Chicago by cabin class
Find flights from Sydney to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Sydney and Chicago flights
Browse other Sydney and Chicago flight options. Last updated on August 10, 2026.
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 August 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from Sydney to Chicago
Discover the top 2 airlines 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 2,558,603 searches. Data last updated August 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$970 | Average$1,633 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$1,113 | Average$1,279 | FlexibilityNo cancel fee | On-time69% |