Flights from Chicago to Australia in September: flights from $950 one way, Nov 2026–Sep 2027
September is Australia's spring: mild in Sydney and Melbourne, dry season in the north, and whale season on the east coast. Fares are below the summer peak.
No nonstop seen to Melbourne, Perth, Coolangatta (Gold Coast), Cairns and Hobart on the dates searched recently. No recent searches for Sydney, Brisbane, Adelaide and Canberra.
Where to fly from Chicago to Australia in September: saved round trips within September to Sydney, Melbourne, Brisbane, Perth, Adelaide and Coolangatta (Gold Coast) and more. Pick a destination to see every date, or search your own dates in one tap.
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Saved round trips, entirely within Sep.
Flights for the months ahead
Lowest published fares for the months ahead: $1,188 round trip, Axel-exclusive, Air Canada, 1 stop, May 14–17, 2027; $950 one way, Axel-exclusive, Air Canada, 1 stop, Dec 1, 2026; 144 priced flights on 72 exact dates, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.
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Chicago (ORD) to Sydney (SYD): November 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1470.00 |
| Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1575.00 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1470.00 |
| Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1575.00 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1540.00 |
| Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1650.00 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1045.00 |
| Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1122.00 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1540.00 |
| Nov 24, 2026 – Nov 29, 2026 · 5 nights · Compare return dates departing Nov 24, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1650.00 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1540.00 |
| Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1650.00 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1470.00 |
| Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1575.00 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1470.00 |
| Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1575.00 |
Chicago (ORD) to Sydney (SYD): December 2026
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1645.00 |
| Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1762.50 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1645.00 |
| Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1762.50 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1645.00 |
| Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1762.50 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1282.50 |
| Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1377.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1282.50 |
| Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1377.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 22, 2026 – Dec 27, 2026 · 5 nights · Compare return dates departing Dec 22, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1282.50 |
| Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $1377.00 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 30, 2026 – Jan 2, 2027 · 3 nights · Compare return dates departing Dec 30, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
Chicago (ORD) to Sydney (SYD): January 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1282.50 |
| Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1377.00 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1890.00 |
| Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $2025.00 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1645.00 |
| Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1762.50 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1645.00 |
| Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1762.50 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
Chicago (ORD) to Sydney (SYD): February 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $950.00 |
| Feb 2, 2027 · One way · Compare return dates departing Feb 2, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1020.00 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 4, 2027 – Feb 7, 2027 · 3 nights · Compare return dates departing Feb 4, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 5, 2027 – Feb 8, 2027 · 3 nights · Compare return dates departing Feb 5, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 6, 2027 – Feb 13, 2027 · 7 nights · Compare return dates departing Feb 6, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 19, 2027 – Feb 22, 2027 · 3 nights · Compare return dates departing Feb 19, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1400.00 |
| Feb 20, 2027 – Feb 27, 2027 · 7 nights · Compare return dates departing Feb 20, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1500.00 |
Chicago (ORD) to Sydney (SYD): March 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1358.00 |
| Mar 19, 2027 – Mar 22, 2027 · 3 nights · Compare return dates departing Mar 19, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1455.00 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1477.00 |
| Mar 20, 2027 – Mar 27, 2027 · 7 nights · Compare return dates departing Mar 20, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1582.50 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1510.50 |
| Mar 25, 2027 – Mar 29, 2027 · 4 nights · Compare return dates departing Mar 25, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1624.50 |
Chicago (ORD) to Sydney (SYD): April 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Apr 16, 2027 – Apr 19, 2027 · 3 nights · Compare return dates departing Apr 16, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Apr 17, 2027 – Apr 24, 2027 · 7 nights · Compare return dates departing Apr 17, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
Chicago (ORD) to Sydney (SYD): May 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1187.50 |
| May 14, 2027 – May 17, 2027 · 3 nights · Compare return dates departing May 14, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1282.50 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1187.50 |
| May 15, 2027 – May 22, 2027 · 7 nights · Compare return dates departing May 15, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1282.50 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1187.50 |
| May 28, 2027 – May 31, 2027 · 3 nights · Compare return dates departing May 28, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1282.50 |
Chicago (ORD) to Sydney (SYD): June 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Jun 11, 2027 – Jun 14, 2027 · 3 nights · Compare return dates departing Jun 11, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Jun 12, 2027 – Jun 19, 2027 · 7 nights · Compare return dates departing Jun 12, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
Chicago (ORD) to Sydney (SYD): July 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Jul 2, 2027 – Jul 6, 2027 · 4 nights · Compare return dates departing Jul 2, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Jul 9, 2027 – Jul 12, 2027 · 3 nights · Compare return dates departing Jul 9, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Jul 10, 2027 – Jul 17, 2027 · 7 nights · Compare return dates departing Jul 10, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
Chicago (ORD) to Sydney (SYD): August 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Aug 6, 2027 – Aug 9, 2027 · 3 nights · Compare return dates departing Aug 6, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1250.00 |
| Aug 7, 2027 – Aug 14, 2027 · 7 nights · Compare return dates departing Aug 7, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1350.00 |
Chicago (ORD) to Sydney (SYD): September 2027
| Travel dates | Airline | Stops | Total price |
|---|---|---|---|
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1212.50 |
| Sep 3, 2027 – Sep 6, 2027 · 3 nights · Compare return dates departing Sep 3, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1309.50 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1212.50 |
| Sep 4, 2027 – Sep 11, 2027 · 7 nights · Compare return dates departing Sep 4, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1309.50 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1212.50 |
| Sep 24, 2027 – Sep 27, 2027 · 3 nights · Compare return dates departing Sep 24, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1309.50 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | Air Canada | Up to 1 stop each way | Axel-exclusive $1212.50 |
| Sep 25, 2027 – Oct 2, 2027 · 7 nights · Compare return dates departing Sep 25, 2027 | United Airlines | Up to 1 stop each way | Axel-exclusive $1309.50 |
Hotels in Sydney for these trips
Hotels: under a trip, hotels in Sydney for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.
- Hotels in Sydney for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ The Branksome Hotel And Residences, $449 total · 5★ QT Bondi, $889 total
- Hotels in Sydney for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $424 total · 5★ The Old Clare by Ode Hotels, $824 total
- Hotels in Sydney for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $1,047 total · 5★ The Old Clare by Ode Hotels, $1,855 total
- Hotels in Sydney for these nights (Nov 24–29, 2026 · 5 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $105 total · 4★ The Branksome Hotel And Residences, $834 total · 5★ The Old Clare by Ode Hotels, $1,472 total
- Hotels in Sydney for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ The Branksome Hotel And Residences, $517 total · 5★ The Old Clare by Ode Hotels, $863 total
- Hotels in Sydney for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $478 total · 5★ The Old Clare by Ode Hotels, $762 total
- Hotels in Sydney for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $541 total · 4★ Citadines Connect Sydney Airport, $929 total · 5★ The Old Clare by Ode Hotels, $1,807 total
- Hotels in Sydney for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $312 total · 4★ Citadines Connect Sydney Airport, $438 total · 5★ The Old Clare by Ode Hotels, $915 total
- Hotels in Sydney for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $285 total · 4★ Citadines Connect Sydney Airport, $396 total · 5★ The Old Clare by Ode Hotels, $854 total
- Hotels in Sydney for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $347 total · 4★ Citadines Connect Sydney Airport, $880 total · 5★ QT Sydney, $2,146 total
- Hotels in Sydney for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ The Branksome Hotel And Residences, $501.50 total · 5★ Ovolo Sydney Woolloomooloo, a Wyndham Hotel, $1,058 total
- Hotels in Sydney for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ The Branksome Hotel And Residences, $481.50 total · 5★ QT Sydney, $1,035 total
- Hotels in Sydney for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $939 total · 5★ QT Sydney, $1,557 total
- Hotels in Sydney for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $59 total · 4★ Citadines Connect Sydney Airport, $359 total · 5★ The Old Clare by Ode Hotels, $613 total
- Hotels in Sydney for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $55 total · 4★ Citadines Connect Sydney Airport, $331 total · 5★ The Old Clare by Ode Hotels, $612 total
- Hotels in Sydney for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $225 total · 4★ Citadines Connect Sydney Airport, $758 total · 5★ The Old Clare by Ode Hotels, $1,337 total
- Hotels in Sydney for these nights (Dec 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $85 total · 4★ Citadines Connect Sydney Airport, $586 total · 5★ The Old Clare by Ode Hotels, $982 total
- Hotels in Sydney for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $51 total · 4★ Citadines Connect Sydney Airport, $353 total · 5★ The Old Clare by Ode Hotels, $616 total
- Hotels in Sydney for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $51 total · 4★ Citadines Connect Sydney Airport, $353 total · 5★ The Old Clare by Ode Hotels, $625 total
- Hotels in Sydney for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Little Coogee Hotel, $2,011 total · 4★ Citadines Connect Sydney Airport, $1,142.50 total · 5★ QT Sydney, $2,494 total
- Hotels in Sydney for these nights (Dec 30 – Jan 2, 2027 · 3 nights · 2 adults, 1 room): 3★ Little Coogee Hotel, $971 total · 4★ Citadines Connect Sydney Airport, $613.50 total · 5★ QT Sydney, $1,461 total
- Hotels in Sydney for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ Little Coogee Hotel, $895 total · 4★ Citadines Connect Sydney Airport, $551.50 total · 5★ QT Sydney, $1,287 total
- Hotels in Sydney for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ Little Coogee Hotel, $687 total · 4★ Citadines Connect Sydney Airport, $423 total · 5★ The Old Clare by Ode Hotels, $937 total
- Hotels in Sydney for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $653 total · 5★ The Old Clare by Ode Hotels, $1,431 total
- Hotels in Sydney for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $311 total · 5★ The Old Clare by Ode Hotels, $593 total
- Hotels in Sydney for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $286 total · 5★ The Old Clare by Ode Hotels, $545 total
- Hotels in Sydney for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $640 total · 5★ The Old Clare by Ode Hotels, $1,203 total
- Hotels in Sydney for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $302 total · 5★ The Old Clare by Ode Hotels, $569 total
- Hotels in Sydney for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $278 total · 5★ The Old Clare by Ode Hotels, $551 total
- Hotels in Sydney for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $646 total · 5★ The Old Clare by Ode Hotels, $1,216 total
- Hotels in Sydney for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $307 total · 5★ The Old Clare by Ode Hotels, $568 total
- Hotels in Sydney for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $278 total · 5★ The Old Clare by Ode Hotels, $585 total
- Hotels in Sydney for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $639 total · 5★ The Star Grand Residences, $1,295 total
- Hotels in Sydney for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $307 total · 5★ The Star Grand Residences, $590 total
- Hotels in Sydney for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $283 total · 5★ The Old Clare by Ode Hotels, $576 total
- Hotels in Sydney for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $752 total · 5★ The Old Clare by Ode Hotels, $1,532 total
- Hotels in Sydney for these nights (Feb 4–7, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $63 total · 4★ Citadines Connect Sydney Airport, $388 total · 5★ The Old Clare by Ode Hotels, $716 total
- Hotels in Sydney for these nights (Feb 5–8, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $147 total · 4★ Citadines Connect Sydney Airport, $338 total · 5★ The Old Clare by Ode Hotels, $671 total
- Hotels in Sydney for these nights (Feb 6–13, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $675 total · 4★ Citadines Connect Sydney Airport, $782 total · 5★ QT Sydney, $1,828 total
- Hotels in Sydney for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $339 total · 4★ Citadines Connect Sydney Airport, $336 total · 5★ The Star Grand Residences, $776 total
- Hotels in Sydney for these nights (Feb 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $343.50 total · 4★ Citadines Connect Sydney Airport, $428 total · 5★ QT Bondi, $986 total
- Hotels in Sydney for these nights (Feb 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $797.50 total · 4★ Citadines Connect Sydney Airport, $895 total · 5★ The Star Grand Residences, $1,957 total
- Hotels in Sydney for these nights (Mar 19–22, 2027 · 3 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $342 total · 4★ Citadines Connect Sydney Airport, $344 total · 5★ The Old Clare by Ode Hotels, $680 total
- Hotels in Sydney for these nights (Mar 20–27, 2027 · 7 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $791 total · 4★ Citadines Connect Sydney Airport, $773 total · 5★ The Old Clare by Ode Hotels, $1,538 total
- Hotels in Sydney for these nights (Mar 25–29, 2027 · 4 nights · 2 adults, 1 room): 3★ Dalziel Lodge, $467 total · 4★ Citadines Connect Sydney Airport, $437 total · 5★ Sofitel Sydney Darling Harbour, $856 total
- Hotels in Sydney for these nights (Apr 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ Great Southern Hotel Sydney, $324 total · 4★ Citadines Connect Sydney Airport, $263 total · 5★ The Old Clare by Ode Hotels, $575 total
- Hotels in Sydney for these nights (Apr 17–24, 2027 · 7 nights · 2 adults, 1 room): 3★ Great Southern Hotel Sydney, $703 total · 4★ Citadines Connect Sydney Airport, $639 total · 5★ The Star Grand Residences, $1,445 total
- Hotels in Sydney for these nights (May 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (May 15–22, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (May 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Jun 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Jun 12–19, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Jul 2–6, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Jul 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Jul 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Aug 6–9, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Aug 7–14, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Sep 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Sep 4–11, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Sep 24–27, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
- Hotels in Sydney for these nights (Sep 25 – Oct 2, 2027 · 7 nights · 2 adults, 1 room): 3★ Hotel Challis Potts Point · 4★ The Capitol Hotel Sydney · 5★ Capella Sydney Hotel
Route overview: Chicago to Sydney (SYD) flight deals
2026-11-19 → 2026-11-22 · Axel-exclusive $1470.00
- Air Canada AC1049 / AC37: ORD 2026-11-19 15:30:00 → SYD 2026-11-21 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2026-11-19 15:30:00 → YVR 2026-11-19 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2026-11-19 21:00:00 → SYD 2026-11-21 06:55:00.
- Air Canada AC34 / AC1048: SYD 2026-11-22 11:20:00 → ORD 2026-11-22 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2026-11-22 11:20:00 → YVR 2026-11-22 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2026-11-22 09:25:00 → ORD 2026-11-22 14:37:00.
2026-11-19 → 2026-11-22 · Axel-exclusive $1575.00
- United Airlines UA649 / UA863: ORD 2026-11-19 18:43:00 → SYD 2026-11-21 09:20:00; 1 stop(s) via SFO; 1297 minutes. Local airport times.
- UA649: ORD 2026-11-19 18:43:00 → SFO 2026-11-19 21:47:00; layover at SFO: 78 minutes.
- UA863: SFO 2026-11-19 23:05:00 → SYD 2026-11-21 09:20:00.
- United Airlines UA842 / UA1946: SYD 2026-11-22 11:20:00 → ORD 2026-11-22 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2026-11-22 11:20:00 → LAX 2026-11-22 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2026-11-22 08:25:00 → ORD 2026-11-22 14:43:00.
2026-11-24 · one way · Axel-exclusive $1045.00
- Air Canada AC1049 / AC37: ORD 2026-11-24 15:30:00 → SYD 2026-11-26 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2026-11-24 15:30:00 → YVR 2026-11-24 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2026-11-24 21:00:00 → SYD 2026-11-26 06:55:00.
2026-11-24 · one way · Axel-exclusive $1122.00
- United Airlines UA649 / UA863: ORD 2026-11-24 18:43:00 → SYD 2026-11-26 09:20:00; 1 stop(s) via SFO; 1297 minutes. Local airport times.
- UA649: ORD 2026-11-24 18:43:00 → SFO 2026-11-24 21:47:00; layover at SFO: 78 minutes.
- UA863: SFO 2026-11-24 23:05:00 → SYD 2026-11-26 09:20:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $1470.00
- Air Canada AC1049 / AC37: ORD 2026-11-28 15:30:00 → SYD 2026-11-30 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2026-11-28 15:30:00 → YVR 2026-11-28 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2026-11-28 21:00:00 → SYD 2026-11-30 06:55:00.
- Air Canada AC34 / AC1048: SYD 2026-12-05 11:20:00 → ORD 2026-12-05 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2026-12-05 11:20:00 → YVR 2026-12-05 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2026-12-05 09:25:00 → ORD 2026-12-05 14:37:00.
2026-11-28 → 2026-12-05 · Axel-exclusive $1575.00
- United Airlines UA649 / UA863: ORD 2026-11-28 18:43:00 → SYD 2026-11-30 09:20:00; 1 stop(s) via SFO; 1297 minutes. Local airport times.
- UA649: ORD 2026-11-28 18:43:00 → SFO 2026-11-28 21:47:00; layover at SFO: 78 minutes.
- UA863: SFO 2026-11-28 23:05:00 → SYD 2026-11-30 09:20:00.
- United Airlines UA842 / UA1946: SYD 2026-12-05 11:20:00 → ORD 2026-12-05 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2026-12-05 11:20:00 → LAX 2026-12-05 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2026-12-05 08:25:00 → ORD 2026-12-05 14:43:00.
2026-12-12 → 2026-12-19 · Axel-exclusive $1890.00
- Air Canada AC1049 / AC37: ORD 2026-12-12 15:30:00 → SYD 2026-12-14 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2026-12-12 15:30:00 → YVR 2026-12-12 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2026-12-12 21:00:00 → SYD 2026-12-14 06:55:00.
- Air Canada AC34 / AC1048: SYD 2026-12-19 11:20:00 → ORD 2026-12-19 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2026-12-19 11:20:00 → YVR 2026-12-19 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2026-12-19 09:25:00 → ORD 2026-12-19 14:37:00.
2026-12-12 → 2026-12-19 · Axel-exclusive $2025.00
- United Airlines UA649 / UA863: ORD 2026-12-12 18:43:00 → SYD 2026-12-14 09:20:00; 1 stop(s) via SFO; 1297 minutes. Local airport times.
- UA649: ORD 2026-12-12 18:43:00 → SFO 2026-12-12 21:47:00; layover at SFO: 78 minutes.
- UA863: SFO 2026-12-12 23:05:00 → SYD 2026-12-14 09:20:00.
- United Airlines UA842 / UA1946: SYD 2026-12-19 11:20:00 → ORD 2026-12-19 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2026-12-19 11:20:00 → LAX 2026-12-19 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2026-12-19 08:25:00 → ORD 2026-12-19 14:43:00.
2026-12-25 → 2026-12-28 · Axel-exclusive $1890.00
- Air Canada AC1049 / AC37: ORD 2026-12-25 15:30:00 → SYD 2026-12-27 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2026-12-25 15:30:00 → YVR 2026-12-25 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2026-12-25 21:00:00 → SYD 2026-12-27 06:55:00.
- Air Canada AC34 / AC1048: SYD 2026-12-28 11:20:00 → ORD 2026-12-28 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2026-12-28 11:20:00 → YVR 2026-12-28 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2026-12-28 09:25:00 → ORD 2026-12-28 14:37:00.
2026-12-25 → 2026-12-28 · Axel-exclusive $2025.00
- United Airlines UA2326 / UA839: ORD 2026-12-25 17:45:00 → SYD 2026-12-27 09:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2026-12-25 17:45:00 → LAX 2026-12-25 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2026-12-25 22:40:00 → SYD 2026-12-27 09:05:00.
- United Airlines UA842 / UA1946: SYD 2026-12-28 11:20:00 → ORD 2026-12-28 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2026-12-28 11:20:00 → LAX 2026-12-28 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2026-12-28 08:25:00 → ORD 2026-12-28 14:43:00.
2027-01-07 → 2027-01-10 · Axel-exclusive $1890.00
- Air Canada AC1049 / AC37: ORD 2027-01-07 15:30:00 → SYD 2027-01-09 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-01-07 15:30:00 → YVR 2027-01-07 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-01-07 21:00:00 → SYD 2027-01-09 06:55:00.
- Air Canada AC34 / AC1048: SYD 2027-01-10 11:20:00 → ORD 2027-01-10 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-01-10 11:20:00 → YVR 2027-01-10 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-01-10 09:25:00 → ORD 2027-01-10 14:37:00.
2027-01-07 → 2027-01-10 · Axel-exclusive $2025.00
- United Airlines UA2326 / UA839: ORD 2027-01-07 17:45:00 → SYD 2027-01-09 09:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2027-01-07 17:45:00 → LAX 2027-01-07 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2027-01-07 22:40:00 → SYD 2027-01-09 09:05:00.
- United Airlines UA842 / UA1946: SYD 2027-01-10 11:20:00 → ORD 2027-01-10 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-01-10 11:20:00 → LAX 2027-01-10 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-01-10 08:25:00 → ORD 2027-01-10 14:43:00.
2027-01-21 → 2027-01-24 · Axel-exclusive $1400.00
- Air Canada AC1049 / AC37: ORD 2027-01-21 15:30:00 → SYD 2027-01-23 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-01-21 15:30:00 → YVR 2027-01-21 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-01-21 21:00:00 → SYD 2027-01-23 06:55:00.
- Air Canada AC34 / AC1048: SYD 2027-01-24 11:20:00 → ORD 2027-01-24 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-01-24 11:20:00 → YVR 2027-01-24 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-01-24 09:25:00 → ORD 2027-01-24 14:37:00.
2027-01-21 → 2027-01-24 · Axel-exclusive $1500.00
- United Airlines UA2326 / UA839: ORD 2027-01-21 17:45:00 → SYD 2027-01-23 09:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2027-01-21 17:45:00 → LAX 2027-01-21 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2027-01-21 22:40:00 → SYD 2027-01-23 09:05:00.
- United Airlines UA842 / UA1946: SYD 2027-01-24 11:20:00 → ORD 2027-01-24 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-01-24 11:20:00 → LAX 2027-01-24 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-01-24 08:25:00 → ORD 2027-01-24 14:43:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $1400.00
- Air Canada AC1049 / AC37: ORD 2027-02-04 15:30:00 → SYD 2027-02-06 06:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-02-04 15:30:00 → YVR 2027-02-04 19:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-02-04 21:00:00 → SYD 2027-02-06 06:55:00.
- Air Canada AC34 / AC1048: SYD 2027-02-07 11:20:00 → ORD 2027-02-07 14:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-02-07 11:20:00 → YVR 2027-02-07 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-02-07 09:25:00 → ORD 2027-02-07 14:37:00.
2027-02-04 → 2027-02-07 · Axel-exclusive $1500.00
- United Airlines UA2326 / UA839: ORD 2027-02-04 17:45:00 → SYD 2027-02-06 09:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2027-02-04 17:45:00 → LAX 2027-02-04 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2027-02-04 22:40:00 → SYD 2027-02-06 09:05:00.
- United Airlines UA842 / UA1946: SYD 2027-02-07 11:20:00 → ORD 2027-02-07 14:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-02-07 11:20:00 → LAX 2027-02-07 06:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-02-07 08:25:00 → ORD 2027-02-07 14:43:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $1358.00
- Air Canada AC1049 / AC37: ORD 2027-03-19 15:30:00 → SYD 2027-03-21 05:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-03-19 15:30:00 → YVR 2027-03-19 18:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-03-19 20:00:00 → SYD 2027-03-21 05:55:00.
- Air Canada AC34 / AC1048: SYD 2027-03-22 11:20:00 → ORD 2027-03-22 15:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-03-22 11:20:00 → YVR 2027-03-22 07:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-03-22 09:25:00 → ORD 2027-03-22 15:37:00.
2027-03-19 → 2027-03-22 · Axel-exclusive $1455.00
- United Airlines UA2326 / UA839: ORD 2027-03-19 17:45:00 → SYD 2027-03-21 08:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2027-03-19 17:45:00 → LAX 2027-03-19 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2027-03-19 22:40:00 → SYD 2027-03-21 08:05:00.
- United Airlines UA842 / UA1946: SYD 2027-03-22 11:20:00 → ORD 2027-03-22 15:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-03-22 11:20:00 → LAX 2027-03-22 07:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-03-22 09:25:00 → ORD 2027-03-22 15:43:00.
2027-05-15 → 2027-05-22 · Axel-exclusive $1187.50
- Air Canada AC1049 / AC37: ORD 2027-05-15 15:30:00 → SYD 2027-05-17 04:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-05-15 15:30:00 → YVR 2027-05-15 18:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-05-15 20:00:00 → SYD 2027-05-17 04:55:00.
- Air Canada AC34 / AC1048: SYD 2027-05-22 11:20:00 → ORD 2027-05-22 16:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-05-22 11:20:00 → YVR 2027-05-22 08:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-05-22 10:25:00 → ORD 2027-05-22 16:37:00.
2027-05-15 → 2027-05-22 · Axel-exclusive $1282.50
- United Airlines UA2326 / UA839: ORD 2027-05-15 17:45:00 → SYD 2027-05-17 07:05:00; 1 stop(s) via LAX; 1340 minutes. Local airport times.
- UA2326: ORD 2027-05-15 17:45:00 → LAX 2027-05-15 20:25:00; layover at LAX: 135 minutes.
- UA839: LAX 2027-05-15 22:40:00 → SYD 2027-05-17 07:05:00.
- United Airlines UA842 / UA1946: SYD 2027-05-22 11:20:00 → ORD 2027-05-22 16:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-05-22 11:20:00 → LAX 2027-05-22 08:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-05-22 10:25:00 → ORD 2027-05-22 16:43:00.
2027-07-10 → 2027-07-17 · Axel-exclusive $1250.00
- Air Canada AC1049 / AC37: ORD 2027-07-10 15:30:00 → SYD 2027-07-12 04:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-07-10 15:30:00 → YVR 2027-07-10 18:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-07-10 20:00:00 → SYD 2027-07-12 04:55:00.
- Air Canada AC34 / AC1048: SYD 2027-07-17 11:20:00 → ORD 2027-07-17 16:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-07-17 11:20:00 → YVR 2027-07-17 08:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-07-17 10:25:00 → ORD 2027-07-17 16:37:00.
2027-07-10 → 2027-07-17 · Axel-exclusive $1400.00
- Delta Air Lines DL756 / DL43: ORD 2027-07-10 14:25:00 → SYD 2027-07-12 04:50:00; 1 stop(s) via LAX; 1405 minutes. Local airport times.
- DL756: ORD 2027-07-10 14:25:00 → LAX 2027-07-10 16:59:00; layover at LAX: 226 minutes.
- DL43: LAX 2027-07-10 20:45:00 → SYD 2027-07-12 04:50:00.
- United Airlines UA842 / UA1946: SYD 2027-07-17 11:20:00 → ORD 2027-07-17 16:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-07-17 11:20:00 → LAX 2027-07-17 08:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-07-17 10:25:00 → ORD 2027-07-17 16:43:00.
2027-09-25 → 2027-10-02 · Axel-exclusive $1212.50
- Air Canada AC1049 / AC37: ORD 2027-09-25 15:30:00 → SYD 2027-09-27 04:55:00; 1 stop(s) via YVR; 1345 minutes. Local airport times.
- AC1049: ORD 2027-09-25 15:30:00 → YVR 2027-09-25 18:17:00; layover at YVR: 103 minutes.
- AC37: YVR 2027-09-25 20:00:00 → SYD 2027-09-27 04:55:00.
- Air Canada AC34 / AC1048: SYD 2027-10-02 11:20:00 → ORD 2027-10-02 16:37:00; 1 stop(s) via YVR; 1217 minutes. Local airport times.
- AC34: SYD 2027-10-02 11:20:00 → YVR 2027-10-02 08:45:00; layover at YVR: 100 minutes.
- AC1048: YVR 2027-10-02 10:25:00 → ORD 2027-10-02 16:37:00.
2027-09-25 → 2027-10-02 · Axel-exclusive $1333.75
- American Airlines AA569 / QF8: ORD 2027-09-25 15:55:00 → SYD 2027-09-27 04:55:00; 1 stop(s) via DFW; 1320 minutes. Local airport times.
- AA569: ORD 2027-09-25 15:55:00 → DFW 2027-09-25 18:41:00; layover at DFW: 124 minutes.
- QF8: DFW 2027-09-25 20:45:00 → SYD 2027-09-27 04:55:00.
- United Airlines UA842 / UA1946: SYD 2027-10-02 11:20:00 → ORD 2027-10-02 16:43:00; 1 stop(s) via LAX; 1223 minutes. Local airport times.
- UA842: SYD 2027-10-02 11:20:00 → LAX 2027-10-02 08:05:00; layover at LAX: 140 minutes.
- UA1946: LAX 2027-10-02 10:25:00 → ORD 2027-10-02 16:43:00.
More dates for this route
- Nov 19, 2026 · Return options
- Nov 27, 2026 · Return options
- Dec 8, 2026 · Return options
- Dec 19, 2026 · Return options
- Dec 29, 2026 · Return options
- Jan 8, 2027 · Return options
- Jan 19, 2027 · Return options
- Jan 30, 2027 · Return options
- Feb 19, 2027 · Return options
- May 14, 2027 · Return options
- Jul 9, 2027 · Return options
- Sep 25, 2027 · Return options
- Hotels in Sydney with Axel
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- Costa Rica: for Christmas · for spring break · in winter · for a week · for 10 days
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- Portugal: in summer · in May · in September · in winter · for 4 days · for a week · for 10 days
- Croatia: in summer · in June · in September · for a week · for 10 days
- Iceland: in summer · in winter · in September · for 4 days · for a week
- Scandinavia: in summer · in winter · in September · for 4 days · for a week · for 10 days
- Eastern Europe: in summer · in May · in September · in December · for a week · for 10 days
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- Southeast Asia: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks · for a month
- Thailand: in winter · in November · in January · in February · for 10 days · for two weeks · for three weeks
- Vietnam: in winter · in November · in February · in spring · for 10 days · for two weeks
- Bali: in summer · in winter · for 10 days · for two weeks · for a month
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Where to go from Chicago
Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.
| Destination | Why go | Flights | Axel-exclusive | Dates | |
|---|---|---|---|---|---|
| Sydney (SYD) | Sydney's harbour, Opera House and beaches | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates | |
| Melbourne (MEL) | Melbourne's laneways, coffee and the Great Ocean Road | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| Brisbane (BNE) | Brisbane's river city and the Gold Coast nearby | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates | |
| Perth (PER) | Perth's beaches and the Margaret River wine region | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| Adelaide (ADL) | Adelaide's wine regions and Kangaroo Island | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates | |
| Coolangatta (Gold Coast) (OOL) | The Gold Coast's surf beaches and theme parks | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| Cairns (CNS) | Cairns, the gateway to the Great Barrier Reef | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
| Canberra (CBR) | Canberra's museums and Parliament | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates | |
| Hobart (HBA) | Hobart, the gateway to Tasmania's wilderness | No nonstop seen | No matching fare saved | Sep 11 – Sep 18, 2027 (suggested) | Search these dates |
Keep exploring
Hotels in Sydney with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Sydney has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Sydney: the 11 best neighborhoods, ranked · Sydney hotels where a family of four can share one room
Hotel details in Sydney: Capella Sydney Hotel 5★ · QT Sydney 5★ · The Capitol Hotel Sydney 4★ · Crystalbrook Albion 4★ · Macleay Hotel 4★ · All 226 hotels in Sydney
For AI assistants
- This page: Flights from Chicago to Australia in September. Round-trip fares from Chicago to Australia in September: Sydney, Melbourne, Brisbane, Perth, Adelaide and Coolangatta (Gold Coast) and more. Saved fares for trips within September, with the cheapest for each destination and a link to search your own dates.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.