$631+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Jun 12 — Jun 191
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
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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 May 13, 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 May 13, 2026.
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Tue 9/89:10 am
SYD
- ORD
2 stops25h 42m
American Airlines
Mon 9/217:01 pm
ORD
- SYD
1 stop21h 04m
American Airlines
Deal found 5/11![American Airlines logo]()
$1,033
This Delta deal was found by Cheapflights users on 5/11. 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
SYD
- ORD
2 stops24h 24m
Delta
Mon 9/213:50 pm
ORD
- SYD
2 stops24h 00m
Delta
Deal found 5/11![Delta logo]()
$1,052
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 10/3111:15 am
SYD
- ORD
1 stop34h 46m
American Airlines
Wed 11/48:35 am
ORD
- SYD
1 stop28h 35m
American Airlines
Deal found 5/12![American Airlines logo]()
$1,073
This American Airlines deal was found by Cheapflights users on 5/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:10 am
SYD
- ORD
1 stop22h 35m
American Airlines
Thu 9/247:01 pm
ORD
- SYD
1 stop21h 04m
American Airlines
Deal found 5/9![American Airlines logo]()
$1,082
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Mon 10/1910:10 am
SYD
- ORD
1 stop22h 40m
American Airlines
Sat 10/313:14 pm
ORD
- SYD
1 stop24h 46m
American Airlines
Deal found 5/8![American Airlines logo]()
$1,083
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Fri 9/119:10 am
SYD
- ORD
1 stop21h 40m
American Airlines
Sun 9/207:01 pm
ORD
- SYD
1 stop21h 04m
American Airlines
Deal found 5/11![American Airlines logo]()
$1,084
This American Airlines deal was found by Cheapflights users on 5/13. 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.
Thu 10/19:10 am
SYD
- ORD
1 stop27h 12m
American Airlines
Fri 10/98:25 pm
ORD
- SYD
1 stop43h 05m
American Airlines
Deal found 5/13![American Airlines logo]()
$1,088
This Ovago deal was found by Cheapflights users on 5/9. 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 Ovago is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:10 am
SYD
- ORD
1 stop22h 35m
Qantas Airways
Thu 9/243:52 pm
ORD
- SYD
1 stop24h 13m
Qantas Airways
Deal found 5/9![Qantas Airways logo]()
$1,091
This American Airlines deal was found by Cheapflights users on 5/11. 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.
Sat 9/1212:00 pm
SYD
- ORD
1 stop21h 24m
American Airlines
Mon 9/217:01 pm
ORD
- SYD
1 stop21h 04m
American Airlines
Deal found 5/11![American Airlines logo]()
$1,092
This KAYAK deal was found by Cheapflights users on 5/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2211:15 am
SYD
- ORD
1 stop29h 44m
Qantas Airways
Sun 11/2911:45 am
ORD
- SYD
1 stop25h 40m
Qantas Airways
Deal found 5/10![Qantas Airways logo]()
$1,098
This Delta deal was found by Cheapflights users on 5/9. 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.
Thu 9/109:15 am
SYD
- MDW
2 stops24h 16m
Delta
Thu 9/241:05 pm
MDW
- SYD
2 stops26h 45m
Delta
Deal found 5/9![Delta logo]()
$1,101
This Delta deal was found by Cheapflights users on 5/8. 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.
Mon 10/1910:15 am
SYD
- MDW
2 stops24h 22m
Delta
Sat 10/311:00 pm
MDW
- SYD
2 stops26h 30m
Delta
Deal found 5/8![Delta logo]()
$1,102
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 May 13, 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 May 13, 2026.
This Alaska Airlines deal was found by Cheapflights users on 5/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/48:45 pm
SYD
- ORD
2 stops37h 05m
Multiple Airlines
Wed 8/128:20 pm
ORD
- SYD
2 stops31h 30m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$1,591
This Qantas Airways deal was found by Cheapflights users on 5/11. 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.
Tue 6/26:00 am
SYD
- ORD
2 stops24h 52m
Qantas Airways
Tue 6/236:59 pm
ORD
- SYD
1 stop21h 06m
Qantas Airways
Deal found 5/11![Qantas Airways logo]()
$1,649
This Delta deal was found by Cheapflights users on 5/13. 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 6/49:15 am
SYD
- MDW
2 stops23h 41m
Delta
Wed 8/121:52 pm
MDW
- SYD
2 stops25h 58m
Delta
Deal found 5/13![Delta logo]()
$1,714
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/58:45 pm
SYD
- ORD
2 stops37h 05m
Multiple Airlines
Wed 8/128:20 pm
ORD
- SYD
2 stops31h 30m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,618
This Delta deal was found by Cheapflights users on 5/13. 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 10/19:15 am
SYD
- MDW
2 stops27h 31m
Delta
Fri 10/912:30 pm
MDW
- SYD
2 stops27h 20m
Delta
Deal found 5/13![Delta logo]()
$1,716
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/318:45 pm
SYD
- ORD
2 stops42h 10m
Multiple Airlines
Wed 6/107:20 am
ORD
- SYD
2 stops44h 30m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,640
This Delta deal was found by Cheapflights users on 5/8. 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.
Thu 5/289:15 am
SYD
- ORD
2 stops22h 36m
Delta
Mon 6/81:46 pm
ORD
- SYD
2 stops26h 04m
Delta
Deal found 5/8![Delta logo]()
$1,717
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:45 pm
SYD
- ORD
2 stops31h 29m
Multiple Airlines
Fri 6/125:42 pm
ORD
- SYD
2 stops34h 08m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,662
This Delta deal was found by Cheapflights users on 5/12. 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 6/119:15 am
SYD
- MDW
2 stops28h 02m
Delta
Mon 7/209:49 am
MDW
- SYD
2 stops30h 01m
Delta
Deal found 5/12![Delta logo]()
$1,718
This Alaska Airlines deal was found by Cheapflights users on 5/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/28:45 pm
SYD
- ORD
3 stops24h 35m
Multiple Airlines
Wed 6/108:05 pm
ORD
- SYD
2 stops31h 45m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,673
This Delta deal was found by Cheapflights users on 5/13. 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 6/219:15 am
SYD
- MDW
2 stops24h 03m
Delta
Sun 7/199:49 am
MDW
- SYD
2 stops30h 01m
Delta
Deal found 5/13![Delta logo]()
$1,765
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 6/98:45 pm
SYD
- ORD
3 stops30h 18m
Multiple Airlines
Thu 6/116:42 pm
ORD
- SYD
2 stops33h 08m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,688
This Delta deal was found by Cheapflights users on 5/9. 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 6/39:15 am
SYD
- MDW
2 stops26h 54m
Delta
Sat 6/131:49 pm
MDW
- SYD
2 stops26h 01m
Delta
Deal found 5/9![Delta logo]()
$1,766
This Alaska Airlines deal was found by Cheapflights users on 5/12. 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 5/268:45 pm
SYD
- ORD
3 stops24h 35m
Multiple Airlines
Fri 5/297:49 pm
ORD
- SYD
2 stops32h 01m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,694
This Delta deal was found by Cheapflights users on 5/12. 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 6/149:15 am
SYD
- MDW
2 stops24h 16m
Delta
Mon 7/209:19 am
MDW
- SYD
2 stops30h 31m
Delta
Deal found 5/12![Delta logo]()
$1,768
This Alaska Airlines deal was found by Cheapflights users on 5/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/118:45 pm
SYD
- ORD
2 stops23h 15m
Multiple Airlines
Thu 7/235:42 pm
ORD
- SYD
2 stops34h 08m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,714
This Delta deal was found by Cheapflights users on 5/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/79:15 am
SYD
- MDW
2 stops28h 02m
Delta
Sun 6/141:26 pm
MDW
- SYD
2 stops26h 24m
Delta
Deal found 5/10![Delta logo]()
$1,770
This Etihad Airways deal was found by Cheapflights users on 5/11. 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 7/123:40 pm
SYD
- ORD
2 stops40h 06m
Multiple Airlines
Sat 7/259:10 pm
ORD
- SYD
1 stop42h 00m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$1,774
This Delta deal was found by Cheapflights users on 5/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:15 am
SYD
- ORD
2 stops25h 15m
Delta
Thu 7/301:44 pm
ORD
- SYD
2 stops26h 06m
Delta
Deal found 5/10![Delta logo]()
$1,826
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated May 13, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated May 13, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 5/12. 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 5/266:00 am
SYD
- ORD
3 stops56h 13m
Multiple Airlines
Fri 5/296:55 am
ORD
- SYD
3 stops37h 55m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,123
This Trip.com deal was found by Cheapflights users on 5/12. 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 5/261:15 pm
SYD
- MDW
3 stops36h 54m
Multiple Airlines
Fri 5/296:00 am
MDW
- SYD
3 stops38h 50m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,139
This Qantas Airways deal was found by Cheapflights users on 5/8. 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.
Wed 5/279:00 am
SYD
- ORD
2 stops25h 33m
Qantas Airways
Mon 6/83:50 pm
ORD
- SYD
2 stops25h 25m
Qantas Airways
Deal found 5/8![Qantas Airways logo]()
$1,383
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/275:50 pm
SYD
- ORD
1 stop27h 44m
Multiple Airlines
Thu 6/117:20 am
ORD
- SYD
2 stops33h 10m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,409
This Qantas Airways deal was found by Cheapflights users on 5/8. 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.
Fri 5/2910:00 pm
SYD
- ORD
2 stops32h 52m
Qantas Airways
Mon 6/83:50 pm
ORD
- SYD
2 stops26h 35m
Qantas Airways
Deal found 5/8![Qantas Airways logo]()
$1,391
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/295:50 pm
SYD
- ORD
1 stop27h 44m
Multiple Airlines
Wed 6/105:29 pm
ORD
- SYD
2 stops47h 01m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$1,408
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:15 pm
SYD
- ORD
3 stops46h 17m
Multiple Airlines
Fri 6/197:20 am
ORD
- SYD
3 stops37h 30m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,166
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:15 pm
SYD
- MDW
3 stops36h 54m
Multiple Airlines
Fri 6/196:00 am
MDW
- SYD
3 stops38h 50m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,637
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Wed 6/312:00 pm
SYD
- MDW
1 stop41h 12m
Multiple Airlines
Sat 6/134:10 pm
MDW
- SYD
2 stops28h 40m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$1,683
This Gurufare deal was found by Cheapflights users on 5/11. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/412:00 pm
SYD
- ORD
1 stop22h 28m
Qantas Airways
Wed 8/128:50 am
ORD
- SYD
1 stop31h 40m
Qantas Airways
Deal found 5/11![Qantas Airways logo]()
$1,384
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/71:15 pm
SYD
- ORD
3 stops46h 17m
Multiple Airlines
Sun 6/146:55 am
ORD
- SYD
3 stops48h 15m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,250
This Trip.com deal was found by Cheapflights users on 5/12. 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 6/142:10 pm
SYD
- ORD
3 stops53h 57m
Multiple Airlines
Mon 7/207:15 am
ORD
- SYD
3 stops37h 35m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$1,158
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 May 13, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated May 13, 2026.
This Trip.com deal was found by Cheapflights users on 5/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/241:15 pm
SYD
- ORD
2 stops32h 04m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$631
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 10/312:00 pm
SYD
- ORD
3 stops39h 02m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$640
This KAYAK deal was found by Cheapflights users on 5/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/109:10 am
SYD
- ORD
1 stop22h 35m
Qantas Airways
Deal found 5/11![Qantas Airways logo]()
$643
This Delta deal was found by Cheapflights users on 5/12. 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
SYD
- ORD
2 stops29h 42m
Delta
Deal found 5/12![Delta logo]()
$649
This Kiwi.com deal was found by Cheapflights users on 5/12. 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 6/101:15 pm
SYD
- ORD
3 stops30h 52m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$656
This KAYAK deal was found by Cheapflights users on 5/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:15 am
SYD
- ORD
1 stop20h 48m
Qantas Airways
Deal found 5/12![Qantas Airways logo]()
$709
This Trip.com deal was found by Cheapflights users on 5/13. 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 7/159:10 am
SYD
- ORD
1 stop36h 07m
Multiple Airlines
Deal found 5/13![Multiple Airlines logo]()
$720
This Kiwi.com deal was found by Cheapflights users on 5/11. 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 5/201:20 pm
SYD
- ORD
3 stops44h 30m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$808
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/2712:00 pm
SYD
- MDW
1 stop41h 12m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$935
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 5/2012:00 pm
SYD
- MDW
1 stop41h 12m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$976
This Delta deal was found by Cheapflights users on 5/13. 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 7/159:15 am
SYD
- MDW
2 stops28h 00m
Delta
Deal found 5/13![Delta logo]()
$1,072
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/266:35 pm
SYD
- MDW
3 stops59h 40m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$1,090
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 May 13, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $1,033 (American Airlines) |
One-way from | $631 (Trip.com) |
Popular in | December |
Cheapest in | August |
Average price | $1,166 |
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 May 13, 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 - ORD
SYDORD
Sydney Kingsford Smith
Thu 6/4
8:45 pm-6:50 pm
2 stops37h 05m
Chicago O'Hare Intl
Wed 8/12
8:20 pm-6:50 pm
2 stops31h 30m
$1,591
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 6/5
8:45 pm-6:50 pm
2 stops37h 05m
Chicago O'Hare Intl
Wed 8/12
8:20 pm-6:50 pm
2 stops31h 30m
$1,618
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 5/31
8:45 pm-11:55 pm
2 stops42h 10m
Chicago O'Hare Intl
Wed 6/10
7:20 am-6:50 pm
2 stops44h 30m
$1,640
Quickest round-trip
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 6/2
6:00 am-3:52 pm
2 stops24h 52m
Chicago O'Hare Intl
Tue 6/23
6:59 pm-7:05 am
1 stop21h 06m
$1,649
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 5/30
8:45 pm-1:14 pm
2 stops31h 29m
Chicago O'Hare Intl
Fri 6/12
5:42 pm-6:50 pm
2 stops34h 08m
$1,662
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 6/2
8:45 pm-6:20 am
3 stops24h 35m
Chicago O'Hare Intl
Wed 6/10
8:05 pm-6:50 pm
2 stops31h 45m
$1,673
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 6/9
8:45 pm-12:03 pm
3 stops30h 18m
Chicago O'Hare Intl
Thu 6/11
6:42 pm-6:50 pm
2 stops33h 08m
$1,688
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 5/26
8:45 pm-6:20 am
3 stops24h 35m
Chicago O'Hare Intl
Fri 5/29
7:49 pm-6:50 pm
2 stops32h 01m
$1,694
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 6/4
9:15 am-5:56 pm
2 stops23h 41m
Chicago Midway
Wed 8/12
1:52 pm-6:50 am
2 stops25h 58m
$1,714
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 6/11
8:45 pm-5:00 am
2 stops23h 15m
Chicago O'Hare Intl
Thu 7/23
5:42 pm-6:50 pm
2 stops34h 08m
$1,714
Showing 1-10 of 36 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 May.
| 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
How far ahead should I book a flight from Sydney to Chicago?
The best time to book flights from Sydney to Chicago is 36 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.
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, December is the cheapest month in which you can book a flight from Sydney to Chicago (average of $468). Flying from Sydney to Chicago in February is currently the most expensive (average of $865). 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?
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 May 13, 2026.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.2
Boarding
7.7
Food
7.0
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentTania,May 2026
SYD - DFW
Crew
8.1
Entertainment
7.2
Boarding
7.7
Food
7.0
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentTania,May 2026
SYD - DFW
Crew
8.1
Entertainment
7.2
Boarding
7.7
Food
7.0
Comfort
7.4
Overall
7.5
Reviews
1 / 20
10.0
ExcellentTania,May 2026
SYD - DFW
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
Hammond
Porter
Browse thousands of different options on Cheapflights for your next trip
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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 May 13, 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 May 13, 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 May 13, 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 May 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$795 | Average$1,155 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$970 | Average$1,265 | FlexibilityNo cancel fee | On-time74% |