Fly from
Route
Depart
Return
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 29/9
09:15-18:45
2 stops24h 30m
Chicago O'Hare Intl
Tue 13/10
18:30-07:50
1 stop21h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 11/11
11:35-05:40
2 stops35h 05m
Chicago O'Hare Intl
Mon 16/11
22:45-09:45
1 stop42h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 11/8
20:45-12:03
3 stops30h 18m
Chicago O'Hare Intl
Tue 15/9
19:00-18:50
2 stops32h 50m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Wed 11/11
10:40-18:37
2 stops24h 57m
Chicago Midway
Mon 16/11
13:00-08:30
2 stops26h 30m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 29/9
20:45-06:20
3 stops24h 35m
Chicago O'Hare Intl
Tue 13/10
19:16-18:50
2 stops31h 34m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 1/10
09:15-18:33
2 stops24h 18m
Chicago Midway
Fri 9/10
13:00-07:50
2 stops26h 50m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 1/10
09:15-20:22
2 stops26h 07m
Chicago O'Hare Intl
Fri 9/10
11:30-07:50
2 stops28h 20m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 27/7
09:15-18:18
2 stops24h 03m
Chicago Midway
Mon 10/8
13:25-06:50
2 stops26h 25m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 3/8
09:15-18:01
2 stops23h 46m
Chicago Midway
Mon 17/8
13:51-06:50
2 stops25h 59m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 20/7
09:15-18:25
2 stops24h 10m
Chicago Midway
Tue 4/8
13:25-06:50
2 stops26h 25m
On average, a flight from Sydney to Chicago takes 20 hours 13 minutes. Flights to Chicago from other popular cities in Australia will vary in length. Below are a few examples of popular routes and their flight times.
The most popular airlines flying from Sydney to Chicago are Qantas Airways, Air New Zealand and Air Canada.
The cheapest airlines flying from Sydney to Chicago are Air Canada, Qantas Airways and American Airlines.
In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
Booking 10 days in advance of your planned departure date is, on average, the best time to get cheap flights to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Overall
Boarding
Comfort
Entertainment
Food
Crew
Reviews
Anonymous,Mar 2026
SIN - AKL
Chicago’s regular, grid-like layout makes navigation straightforward, but the “City With Big Shoulders” can be a little too large to get around easily on foot. Fortunately, the city’s public transportation system, including the famous “L” (short for “elevated train tracks”), is efficient, with especially good coverage in the city centre area. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Cycling is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.
Chicago’s major airport is O’Hare International Airport (ORD) located in the city’s northwest corner, about 27 km away from the Loop. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available.
One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water.
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