$664+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Jul 24 — Jul 311
Round-trip
1 adult, Economy
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Find cheap flights from Sydney to Chicago with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 June 24, 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 June 24, 2026.
This Trip.com deal was found by Cheapflights users on 6/23. 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 8/126:05 am
SYD
- ORD
2 stops39h 12m
Multiple Airlines
Wed 8/199:20 am
ORD
- SYD
3 stops35h 30m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$922
This Trip.com deal was found by Cheapflights users on 6/20. 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 8/31:15 pm
SYD
- MDW
3 stops36h 52m
Multiple Airlines
Mon 8/1711:06 am
MDW
- SYD
3 stops33h 44m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$950
This Trip.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/271:15 pm
SYD
- ORD
2 stops32h 02m
Multiple Airlines
Mon 8/1010:16 am
ORD
- SYD
3 stops34h 34m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$976
This Trip.com deal was found by Cheapflights users on 6/20. 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 8/31:15 pm
SYD
- ORD
2 stops32h 02m
Multiple Airlines
Mon 8/177:15 am
ORD
- SYD
3 stops37h 35m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$987
This Trip.com deal was found by Cheapflights users on 6/22. 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 9/31:15 pm
SYD
- ORD
2 stops32h 02m
Multiple Airlines
Sun 9/201:02 pm
ORD
- SYD
3 stops31h 48m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$1,029
This Trip.com deal was found by Cheapflights users on 6/23. 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 8/71:15 pm
SYD
- ORD
2 stops32h 02m
Multiple Airlines
Fri 8/1410:16 am
ORD
- SYD
3 stops34h 34m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$1,038
This BusinessClass deal was found by Cheapflights users on 6/22. 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 BusinessClass is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:50 pm
SYD
- ORD
1 stop36h 04m
Qantas Airways
Sun 9/65:05 pm
ORD
- SYD
1 stop22h 20m
Qantas Airways
Deal found 6/22![Qantas Airways logo]()
$1,046
This BYOjet deal was found by Cheapflights users on 6/22. 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.
Wed 11/119:55 am
SYD
- ORD
2 stops28h 39m
Air New Zealand
Mon 11/161:00 pm
ORD
- SYD
2 stops28h 30m
Air New Zealand
Deal found 6/22![Air New Zealand logo]()
$1,092
This flugladen.de deal was found by Cheapflights users on 6/21. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:10 am
SYD
- ORD
1 stop36h 07m
Multiple Airlines
Tue 8/49:28 am
ORD
- SYD
2 stops31h 02m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,137
This Delta deal was found by Cheapflights users on 6/22. 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 9/39:15 am
SYD
- MDW
2 stops24h 18m
Delta
Sun 9/209:29 am
MDW
- SYD
2 stops30h 21m
Delta
Deal found 6/22![Delta logo]()
$1,173
This Trip.com deal was found by Cheapflights users on 6/21. 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 8/249:10 am
SYD
- MDW
2 stops26h 21m
Multiple Airlines
Thu 9/36:05 am
MDW
- SYD
2 stops34h 25m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,261
This Trip.com deal was found by Cheapflights users on 6/21. 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 8/235:50 pm
SYD
- MDW
2 stops32h 05m
Multiple Airlines
Fri 9/187:25 am
MDW
- SYD
2 stops32h 40m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,300
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 June 24, 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 June 24, 2026.
This BYOjet deal was found by Cheapflights users on 6/23. 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.
Wed 11/119:55 am
SYD
- ORD
2 stops28h 39m
Air New Zealand
Mon 11/161:00 pm
ORD
- SYD
2 stops26h 45m
Air New Zealand
Deal found 6/23![Air New Zealand logo]()
$1,148
This Delta deal was found by Cheapflights users on 6/22. 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 9/39:15 am
SYD
- ORD
1 stop19h 26m
Delta
Sun 9/207:07 am
ORD
- SYD
1 stop32h 43m
Delta
Deal found 6/22![Delta logo]()
$1,173
This Flighttix deal was found by Cheapflights users on 6/19. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:00 pm
SYD
- ORD
1 stop21h 16m
British Airways
Sat 8/110:30 pm
ORD
- SYD
1 stop41h 35m
British Airways
Deal found 6/19![British Airways logo]()
$1,210
This Alaska Airlines deal was found by Cheapflights users on 6/22. 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 11/219:40 pm
SYD
- ORD
3 stops26h 20m
Multiple Airlines
Thu 12/35:55 pm
ORD
- SYD
2 stops32h 50m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$1,417
This Delta deal was found by Cheapflights users on 6/21. 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 9/299:15 am
SYD
- ORD
2 stops23h 46m
Delta
Tue 10/1311:30 am
ORD
- SYD
2 stops28h 20m
Delta
Deal found 6/21![Delta logo]()
$1,176
This Alaska Airlines deal was found by Cheapflights users on 6/22. 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 9/58:45 pm
SYD
- ORD
3 stops24h 35m
Multiple Airlines
Sun 9/66:54 pm
ORD
- SYD
2 stops32h 56m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$1,471
This Delta deal was found by Cheapflights users on 6/23. 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 11/1110:40 am
SYD
- MDW
2 stops24h 57m
Delta
Mon 11/161:00 pm
MDW
- SYD
2 stops26h 30m
Delta
Deal found 6/23![Delta logo]()
$1,457
This SmartFares deal was found by Cheapflights users on 6/19. 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 7/198:45 pm
SYD
- ORD
2 stops30h 18m
Multiple Airlines
Sun 7/266:00 am
ORD
- SYD
2 stops45h 50m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$1,503
This Delta deal was found by Cheapflights users on 6/23. 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 11/1110:40 am
SYD
- ORD
2 stops25h 54m
Delta
Mon 11/166:30 pm
ORD
- SYD
1 stop21h 00m
Delta
Deal found 6/23![Delta logo]()
$1,457
This Alaska Airlines deal was found by Cheapflights users on 6/21. 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 9/298:45 pm
SYD
- ORD
3 stops24h 35m
Multiple Airlines
Tue 10/137:16 pm
ORD
- SYD
2 stops31h 34m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,563
This Delta deal was found by Cheapflights users on 6/23. 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 12/910:40 am
SYD
- MDW
2 stops28h 30m
Delta
Thu 1/1412:30 pm
MDW
- SYD
2 stops27h 00m
Delta
Deal found 6/23![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 6/23. 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 12/910:40 am
SYD
- ORD
1 stop23h 41m
Delta
Thu 1/147:35 am
ORD
- SYD
1 stop31h 55m
Delta
Deal found 6/23![Delta logo]()
$1,469
This Delta deal was found by Cheapflights users on 6/22. 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 11/1210:40 am
SYD
- MDW
2 stops23h 10m
Delta
Mon 11/161:05 pm
MDW
- SYD
2 stops26h 25m
Delta
Deal found 6/22![Delta logo]()
$1,470
This Delta deal was found by Cheapflights users on 6/20. 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 stops24h 18m
Delta
Fri 10/91:00 pm
MDW
- SYD
2 stops26h 50m
Delta
Deal found 6/20![Delta logo]()
$1,587
This Delta deal was found by Cheapflights users on 6/20. 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 7/279:15 am
SYD
- MDW
2 stops24h 03m
Delta
Mon 8/101:25 pm
MDW
- SYD
2 stops26h 25m
Delta
Deal found 6/20![Delta logo]()
$1,665
This Delta deal was found by Cheapflights users on 6/20. 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 8/39:15 am
SYD
- MDW
2 stops23h 46m
Delta
Mon 8/171:51 pm
MDW
- SYD
2 stops25h 59m
Delta
Deal found 6/20![Delta logo]()
$1,667
This Delta deal was found by Cheapflights users on 6/22. 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 8/39:15 am
SYD
- MDW
2 stops23h 46m
Delta
Tue 8/181:51 pm
MDW
- SYD
2 stops25h 59m
Delta
Deal found 6/22![Delta logo]()
$1,667
This Delta deal was found by Cheapflights users on 6/21. 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 7/209:15 am
SYD
- MDW
2 stops24h 10m
Delta
Tue 8/41:25 pm
MDW
- SYD
2 stops26h 25m
Delta
Deal found 6/21![Delta logo]()
$1,667
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated June 24, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated June 24, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/22. 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 6/249:15 am
SYD
- MDW
2 stops24h 16m
Delta
Tue 8/1810:54 am
MDW
- SYD
2 stops28h 56m
Delta
Deal found 6/22![Delta logo]()
$1,667
This Kiwi.com deal was found by Cheapflights users on 6/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/135:50 pm
SYD
- ORD
1 stop27h 27m
Multiple Airlines
Tue 7/286:00 am
ORD
- SYD
2 stops34h 30m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$1,314
This Expedia deal was found by Cheapflights users on 6/19. 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.
Wed 7/159:10 am
SYD
- ORD
1 stop25h 58m
Qantas Airways
Mon 7/273:21 pm
ORD
- SYD
1 stop25h 09m
Qantas Airways
Deal found 6/19![Qantas Airways logo]()
$1,305
This Flighttix deal was found by Cheapflights users on 6/19. 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 Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:00 pm
SYD
- ORD
1 stop21h 16m
British Airways
Sat 8/110:30 pm
ORD
- SYD
1 stop41h 35m
British Airways
Deal found 6/19![British Airways logo]()
$1,210
This flugladen.de deal was found by Cheapflights users on 6/21. 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:10 am
SYD
- ORD
1 stop36h 07m
Multiple Airlines
Tue 8/49:28 am
ORD
- SYD
2 stops31h 02m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,137
This Kiwi.com deal was found by Cheapflights users on 6/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:00 pm
SYD
- MDW
1 stop20h 22m
Multiple Airlines
Tue 8/45:46 pm
MDW
- SYD
2 stops27h 04m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$1,436
This Expedia deal was found by Cheapflights users on 6/22. 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.
Tue 7/219:10 am
SYD
- ORD
1 stop21h 49m
Qantas Airways
Wed 8/53:22 pm
ORD
- SYD
1 stop24h 43m
Qantas Airways
Deal found 6/22![Qantas Airways logo]()
$1,212
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 7/215:50 pm
SYD
- ORD
1 stop27h 27m
Multiple Airlines
Wed 8/59:13 pm
ORD
- SYD
2 stops47h 37m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$1,259
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 7/235:50 pm
SYD
- ORD
1 stop27h 27m
Multiple Airlines
Wed 8/57:15 am
ORD
- SYD
2 stops33h 15m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$1,327
This Delta deal was found by Cheapflights users on 6/23. 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 7/239:15 am
SYD
- MDW
2 stops24h 10m
Delta
Wed 8/51:25 pm
MDW
- SYD
2 stops26h 25m
Delta
Deal found 6/23![Delta logo]()
$1,663
This Trip.com deal was found by Cheapflights users on 6/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/271:15 pm
SYD
- ORD
2 stops32h 02m
Multiple Airlines
Mon 8/1010:16 am
ORD
- SYD
3 stops34h 34m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$976
This Delta deal was found by Cheapflights users on 6/20. 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 7/279:15 am
SYD
- MDW
2 stops24h 03m
Delta
Mon 8/101:25 pm
MDW
- SYD
2 stops26h 25m
Delta
Deal found 6/20![Delta logo]()
$1,665
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 June 24, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated June 24, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/22. 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 8/127:15 pm
SYD
- ORD
3 stops50h 02m
Multiple Airlines
Deal found 6/22![Multiple Airlines logo]()
$664
This Delta deal was found by Cheapflights users on 6/23. 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
1 stop23h 08m
Delta
Deal found 6/23![Delta logo]()
$692
This Delta deal was found by Cheapflights users on 6/23. 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 12/110:40 am
SYD
- ORD
2 stops44h 33m
Delta
Deal found 6/23![Delta logo]()
$698
This Trip.com deal was found by Cheapflights users on 6/19. 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.
Sat 8/19:10 am
SYD
- ORD
1 stop36h 07m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$718
This Kiwi.com deal was found by Cheapflights users on 6/23. 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 7/185:50 pm
SYD
- ORD
1 stop27h 27m
Multiple Airlines
Deal found 6/23![Multiple Airlines logo]()
$733
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/288:45 pm
SYD
- ORD
2 stops48h 32m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$745
This Kiwi.com deal was found by Cheapflights users on 6/21. 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 8/155:50 pm
SYD
- MDW
2 stops41h 42m
Multiple Airlines
Deal found 6/21![Multiple Airlines logo]()
$773
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 8/15:50 pm
SYD
- MDW
2 stops32h 17m
Multiple Airlines
Deal found 6/19![Multiple Airlines logo]()
$810
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/286:20 am
SYD
- MDW
3 stops48h 30m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$825
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/712:00 pm
SYD
- MDW
1 stop42h 50m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$927
This Kiwi.com deal was found by Cheapflights users on 6/20. 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 7/512:00 pm
SYD
- MDW
1 stop23h 32m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$991
This Kiwi.com deal was found by Cheapflights users on 6/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:00 pm
SYD
- MDW
1 stop20h 22m
Multiple Airlines
Deal found 6/20![Multiple Airlines logo]()
$995
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 June 24, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $922 (Trip.com) |
One-way from | $664 (Kiwi.com) |
Popular in | May |
Cheapest in | August |
Average price | $1,321 |
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 June 24, 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
Wed 11/11
9:55 am-9:34 pm
2 stops28h 39m
Chicago O'Hare Intl
Mon 11/16
1:00 pm-8:45 am
2 stops26h 45m
$1,148
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 9/3
9:15 am-1:41 pm
1 stop19h 26m
Chicago O'Hare Intl
Sun 9/20
7:07 am-6:50 am
1 stop32h 43m
$1,173
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 9/29
9:15 am-6:01 pm
2 stops23h 46m
Chicago O'Hare Intl
Tue 10/13
11:30 am-7:50 am
2 stops28h 20m
$1,176
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 7/16
12:00 pm-6:16 pm
1 stop21h 16m
Chicago O'Hare Intl
Sat 8/1
10:30 pm-7:05 am
1 stop41h 35m
$1,210
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 11/21
9:40 pm-7:00 am
3 stops26h 20m
Chicago O'Hare Intl
Thu 12/3
5:55 pm-7:45 pm
2 stops32h 50m
$1,417
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Wed 11/11
10:40 am-6:37 pm
2 stops24h 57m
Chicago Midway
Mon 11/16
1:00 pm-8:30 am
2 stops26h 30m
$1,457
Quickest round-trip
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 11/11
10:40 am-7:34 pm
2 stops25h 54m
Chicago O'Hare Intl
Mon 11/16
6:30 pm-8:30 am
1 stop21h 00m
$1,457
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Wed 12/9
10:40 am-10:10 pm
2 stops28h 30m
Chicago Midway
Thu 1/14
12:30 pm-8:30 am
2 stops27h 00m
$1,469
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 12/9
10:40 am-5:21 pm
1 stop23h 41m
Chicago O'Hare Intl
Thu 1/14
7:35 am-8:30 am
1 stop31h 55m
$1,469
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 11/12
10:40 am-4:50 pm
2 stops23h 10m
Chicago Midway
Mon 11/16
1:05 pm-8:30 am
2 stops26h 25m
$1,470
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 June.
| 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, 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 July is currently the most expensive (average of $920). 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?
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 June 24, 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.
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
Entertainment
7.1
Crew
8.1
Comfort
7.3
Food
6.6
Boarding
7.7
Overall
7.4
Reviews
1 / 20
6.0
GoodROHIT,Jun 2026
IND - EWR
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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
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Alternative routes for Sydney to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
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 June 24, 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 June 24, 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 June 24, 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 June 24, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$970 | Average$1,401 | FlexibilityNo cancel fee | On-time74% | |
| Cheapest$1,113 | Average$1,279 | FlexibilityNo cancel fee | On-time69% |