$440+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
Mar 5 — Mar 121
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 February 3, 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 February 3, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:50 pm
SYD
- ORD
1 stop27h 00m
Multiple Airlines
Mon 5/189:20 pm
ORD
- SYD
1 stop43h 10m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$997
This Kiwi.com deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/251:15 pm
SYD
- ORD
2 stops31h 35m
Multiple Airlines
Sat 5/96:00 am
ORD
- SYD
1 stop34h 30m
Multiple Airlines
Deal found 1/31![Multiple Airlines logo]()
$1,006
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/165:50 pm
SYD
- ORD
1 stop27h 00m
Multiple Airlines
Sun 5/176:00 am
ORD
- SYD
1 stop34h 30m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,041
This Bravofly deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:20 am
SYD
- ORD
1 stop29h 27m
Qantas Airways
Tue 3/108:21 pm
ORD
- SYD
1 stop20h 39m
Qantas Airways
Deal found 2/3![Qantas Airways logo]()
$1,059
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/1911:20 am
SYD
- ORD
1 stop22h 26m
American Airlines
Tue 4/218:57 am
ORD
- SYD
1 stop31h 08m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,068
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/232:05 pm
SYD
- ORD
1 stop20h 40m
American Airlines
Tue 3/105:25 pm
ORD
- SYD
2 stops23h 35m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,075
This American Airlines deal was found by Cheapflights users on 2/3. 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 10/610:10 am
SYD
- ORD
1 stop21h 53m
American Airlines
Mon 10/127:03 pm
ORD
- SYD
1 stop21h 02m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,079
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/241:15 pm
SYD
- ORD
2 stops31h 35m
Multiple Airlines
Sun 5/106:00 am
ORD
- SYD
1 stop34h 30m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$1,082
This BYOjet deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:20 am
SYD
- ORD
2 stops22h 25m
Air Canada
Mon 3/303:40 pm
ORD
- SYD
1 stop24h 40m
Air Canada
Deal found 2/1![Air Canada logo]()
$1,087
This Delta deal was found by Cheapflights users on 2/3. 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 3/199:40 am
SYD
- MDW
2 stops24h 14m
Delta
Tue 4/2112:53 pm
MDW
- SYD
2 stops26h 57m
Delta
Deal found 2/3![Delta logo]()
$1,199
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/211:05 pm
SYD
- MDW
1 stop23h 16m
Multiple Airlines
Sat 3/289:16 pm
MDW
- SYD
1 stop41h 39m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,381
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:15 am
SYD
- MDW
2 stops24h 21m
Delta
Sun 5/101:59 pm
MDW
- SYD
2 stops25h 51m
Delta
Deal found 2/1![Delta logo]()
$1,492
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 February 3, 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 February 3, 2026.
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1911:20 am
SYD
- ORD
2 stops24h 20m
American Airlines
Tue 4/214:40 pm
ORD
- SYD
2 stops23h 25m
American Airlines
Deal found 2/2![American Airlines logo]()
$1,071
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/229:30 am
SYD
- ORD
1 stop26h 05m
United Airlines
Sun 7/192:40 pm
ORD
- SYD
1 stop25h 20m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,097
This Qantas Airways deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Qantas Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/255:45 pm
SYD
- ORD
2 stops22h 51m
Multiple Airlines
Mon 3/24:49 pm
ORD
- SYD
1 stop21h 06m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,137
This Air Canada deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1910:25 am
SYD
- ORD
3 stops37h 35m
Air Canada
Tue 4/218:42 am
ORD
- SYD
2 stops31h 38m
Air Canada
Deal found 2/2![Air Canada logo]()
$1,152
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/199:40 am
SYD
- MDW
2 stops24h 14m
Delta
Tue 4/2112:53 pm
MDW
- SYD
2 stops26h 57m
Delta
Deal found 2/1![Delta logo]()
$1,202
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:05 pm
SYD
- ORD
1 stop24h 20m
American Airlines
Mon 3/29:29 am
ORD
- SYD
1 stop28h 26m
American Airlines
Deal found 2/2![American Airlines logo]()
$1,106
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/2112:10 pm
SYD
- ORD
1 stop20h 52m
United Airlines
Sat 3/289:15 pm
ORD
- SYD
1 stop42h 40m
United Airlines
Deal found 2/2![United Airlines logo]()
$1,138
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/119:40 am
SYD
- MDW
2 stops23h 42m
Delta
Mon 3/3010:45 am
MDW
- SYD
2 stops29h 05m
Delta
Deal found 2/1![Delta logo]()
$1,202
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:20 am
SYD
- ORD
2 stops23h 25m
American Airlines
Mon 3/94:44 pm
ORD
- SYD
1 stop24h 16m
American Airlines
Deal found 2/2![American Airlines logo]()
$1,123
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/289:30 am
SYD
- ORD
1 stop20h 05m
United Airlines
Sun 7/192:40 pm
ORD
- SYD
1 stop25h 20m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,138
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/269:30 am
SYD
- ORD
1 stop27h 16m
United Airlines
Sat 7/259:33 pm
ORD
- SYD
1 stop42h 22m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,138
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2010:20 am
SYD
- ORD
1 stop19h 31m
United Airlines
Sat 7/189:20 pm
ORD
- SYD
1 stop42h 40m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,138
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:15 am
SYD
- MDW
2 stops24h 21m
Delta
Sun 5/101:59 pm
MDW
- SYD
2 stops25h 51m
Delta
Deal found 2/1![Delta logo]()
$1,492
This United Airlines deal was found by Cheapflights users on 2/3. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/219:30 am
SYD
- ORD
1 stop26h 05m
United Airlines
Sun 7/192:40 pm
ORD
- SYD
1 stop25h 20m
United Airlines
Deal found 2/3![United Airlines logo]()
$1,150
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/259:15 am
SYD
- MDW
2 stops24h 21m
Delta
Sat 5/91:22 pm
MDW
- SYD
2 stops26h 28m
Delta
Deal found 1/31![Delta logo]()
$1,544
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/89:15 am
SYD
- MDW
2 stops24h 16m
Delta
Wed 7/151:00 pm
MDW
- SYD
2 stops26h 50m
Delta
Deal found 2/2![Delta logo]()
$1,625
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:40 am
SYD
- MDW
2 stops23h 57m
Delta
Mon 3/91:10 pm
MDW
- SYD
2 stops26h 15m
Delta
Deal found 2/2![Delta logo]()
$1,649
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/109:15 am
SYD
- MDW
2 stops24h 16m
Delta
Sun 7/262:00 pm
MDW
- SYD
2 stops25h 50m
Delta
Deal found 2/1![Delta logo]()
$1,677
This Delta deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/110:40 am
SYD
- MDW
2 stops24h 05m
Delta
Sun 3/82:05 pm
MDW
- SYD
2 stops25h 20m
Delta
Deal found 1/31![Delta logo]()
$1,701
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:40 am
SYD
- MDW
2 stops24h 05m
Delta
Mon 3/99:30 am
MDW
- SYD
2 stops29h 55m
Delta
Deal found 2/2![Delta logo]()
$1,744
Last-minute flights from Sydney to ChicagoDiscover last-minute flight deals from Sydney to Chicago. Data last updated February 3, 2026 and is based on user searches.
Discover last-minute flight deals from Sydney to Chicago. Data last updated February 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:20 am
SYD
- ORD
2 stops23h 25m
American Airlines
Mon 3/94:44 pm
ORD
- SYD
1 stop24h 16m
American Airlines
Deal found 2/2![American Airlines logo]()
$1,123
This Aunt Betty deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aunt Betty is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/222:05 pm
SYD
- ORD
1 stop22h 35m
Qantas Airways
Mon 3/97:29 pm
ORD
- SYD
1 stop21h 31m
Qantas Airways
Deal found 2/2![Qantas Airways logo]()
$1,124
This Bravofly deal was found by Cheapflights users on 2/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Bravofly is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:20 am
SYD
- ORD
1 stop29h 27m
Qantas Airways
Tue 3/108:21 pm
ORD
- SYD
1 stop20h 39m
Qantas Airways
Deal found 2/3![Qantas Airways logo]()
$1,059
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/232:05 pm
SYD
- ORD
1 stop20h 40m
American Airlines
Tue 3/105:25 pm
ORD
- SYD
2 stops23h 35m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,075
This BYOjet deal was found by Cheapflights users on 2/3. 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 2/231:55 pm
SYD
- ORD
2 stops26h 04m
Air New Zealand
Tue 3/102:35 pm
ORD
- SYD
2 stops26h 10m
Air New Zealand
Deal found 2/3![Air New Zealand logo]()
$1,090
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/252:05 pm
SYD
- ORD
1 stop24h 20m
American Airlines
Mon 3/29:29 am
ORD
- SYD
1 stop28h 26m
American Airlines
Deal found 2/2![American Airlines logo]()
$1,106
This Jetabroad deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:55 pm
SYD
- ORD
2 stops32h 17m
Air New Zealand
Mon 3/912:54 pm
ORD
- SYD
2 stops27h 51m
Air New Zealand
Deal found 2/2![Air New Zealand logo]()
$1,108
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:40 am
SYD
- MDW
2 stops23h 57m
Delta
Mon 3/91:10 pm
MDW
- SYD
2 stops26h 15m
Delta
Deal found 2/2![Delta logo]()
$1,649
This BYOjet deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure BYOjet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:20 am
SYD
- ORD
2 stops22h 25m
Air Canada
Mon 3/303:40 pm
ORD
- SYD
1 stop24h 40m
Air Canada
Deal found 2/1![Air Canada logo]()
$1,087
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/1911:20 am
SYD
- ORD
1 stop22h 26m
American Airlines
Tue 4/218:57 am
ORD
- SYD
1 stop31h 08m
American Airlines
Deal found 2/3![American Airlines logo]()
$1,068
This Delta deal was found by Cheapflights users on 2/3. 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 3/199:40 am
SYD
- MDW
2 stops24h 14m
Delta
Tue 4/2112:53 pm
MDW
- SYD
2 stops26h 57m
Delta
Deal found 2/3![Delta logo]()
$1,199
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/211:05 pm
SYD
- MDW
1 stop23h 16m
Multiple Airlines
Sat 3/289:16 pm
MDW
- SYD
1 stop41h 39m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,381
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 February 3, 2026.
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated February 3, 2026.
This Trip.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/151:15 pm
SYD
- ORD
2 stops31h 35m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:00 pm
SYD
- ORD
2 stops31h 49m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 2/82:00 pm
SYD
- ORD
3 stops49h 46m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/62:00 pm
SYD
- ORD
2 stops31h 49m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$480
This Kiwi.com deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/171:15 pm
SYD
- ORD
2 stops32h 13m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$494
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/252:00 pm
SYD
- ORD
2 stops30h 49m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$510
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/242:00 pm
SYD
- ORD
3 stops34h 23m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$515
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/232:00 pm
SYD
- ORD
2 stops30h 49m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$528
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/72:00 pm
SYD
- MDW
2 stops23h 21m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$612
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/157:45 pm
SYD
- MDW
3 stops41h 36m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$686
This Kiwi.com deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/69:20 pm
SYD
- MDW
3 stops40h 01m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$702
This Delta deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/159:15 am
SYD
- MDW
2 stops28h 13m
Delta
Deal found 2/1![Delta logo]()
$918
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 February 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $997 (Kiwi.com) |
One-way from | $440 (Trip.com) |
Popular in | December |
Cheapest in | March |
Average price | $1,012 |
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 February 3, 2026.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.
Fly from
Sydney
Fly to
Chicago
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 3/19
11:20 am-7:40 pm
2 stops24h 20m
Chicago O'Hare Intl
Tue 4/21
4:40 pm-7:05 am
2 stops23h 25m
$1,071
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 6/22
9:30 am-8:35 pm
1 stop26h 05m
Chicago O'Hare Intl
Sun 7/19
2:40 pm-7:00 am
1 stop25h 20m
$1,097
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 2/25
2:05 pm-9:25 pm
1 stop24h 20m
Chicago O'Hare Intl
Mon 3/2
9:29 am-6:55 am
1 stop28h 26m
$1,106
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 2/22
11:20 am-5:45 pm
2 stops23h 25m
Chicago O'Hare Intl
Mon 3/9
4:44 pm-9:00 am
1 stop24h 16m
$1,123
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 2/25
5:45 pm-11:36 pm
2 stops22h 51m
Chicago O'Hare Intl
Mon 3/2
4:49 pm-6:55 am
1 stop21h 06m
$1,137
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 3/21
12:10 pm-5:02 pm
1 stop20h 52m
Chicago O'Hare Intl
Sat 3/28
9:15 pm-7:55 am
1 stop42h 40m
$1,138
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 6/28
9:30 am-2:35 pm
1 stop20h 05m
Chicago O'Hare Intl
Sun 7/19
2:40 pm-7:00 am
1 stop25h 20m
$1,138
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 6/26
9:30 am-9:46 pm
1 stop27h 16m
Chicago O'Hare Intl
Sat 7/25
9:33 pm-6:55 am
1 stop42h 22m
$1,138
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 6/20
10:20 am-2:51 pm
1 stop19h 31m
Chicago O'Hare Intl
Sat 7/18
9:20 pm-7:00 am
1 stop42h 40m
$1,138
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 6/21
9:30 am-8:35 pm
1 stop26h 05m
Chicago O'Hare Intl
Sun 7/19
2:40 pm-7:00 am
1 stop25h 20m
$1,150
Showing 1-10 of 38 results
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 February.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 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?
Use this chart to determine the optimal time to book a round-trip flight from Sydney to Chicago. Price data was last updated on January 30, 2026.
The best time to book flights from Sydney to Chicago is 82 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, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $620). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,034). 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.
What’s the top layover airport for flights from Sydney to Chicago?
Share of 1-stop round-trip flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.
Los Angeles (LAX) – chosen by Cheapflights users on 40% of 1-stop itineraries from Sydney to Chicago on Cheapflights.
What’s the cheapest layover airport for flights from Sydney to Chicago?
Average round-trip fare for 1-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.
Vancouver (YVR) is the most affordable 1-stop option, with an average round-trip price of $1,323.
What’s the fastest layover option from Sydney to Chicago?
Shortest average travel time for 1-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.
Flights via Los Angeles (LAX) have the shortest average one-way travel time for 1-stop routes: 20h 09m.
Which airport typically offers the quickest layover for flights from Sydney to Chicago?
Average layover duration for 1-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via Los Angeles (LAX) offer the fastest connection on this route, with an average layover time of 2h 11m.
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 February 3, 2026.
Read through reviews of airlines operating flights from Sydney to Chicago, such as Qantas Airways, United Airlines, and Air Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.2
Comfort
7.5
Food
7.0
Crew
8.2
Overall
7.5
Boarding
7.7
Reviews
1 / 20
2.0
MediocreMidhat,Jan 2026
WYA - ADL
Entertainment
7.2
Comfort
7.5
Food
7.0
Crew
8.2
Overall
7.5
Boarding
7.7
Reviews
1 / 20
2.0
MediocreMidhat,Jan 2026
WYA - ADL
Entertainment
7.2
Comfort
7.5
Food
7.0
Crew
8.2
Overall
7.5
Boarding
7.7
Reviews
1 / 20
2.0
MediocreMidhat,Jan 2026
WYA - ADL
Entertainment
7.2
Comfort
7.5
Food
7.0
Crew
8.2
Overall
7.5
Boarding
7.7
Reviews
1 / 20
2.0
MediocreMidhat,Jan 2026
WYA - ADL
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 locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
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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.
Top airline flying from Sydney to Chicago
Discover the top airline that operate flights from Sydney to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$646 | Average$970 | FlexibilityNo cancel fee | On-time74% |