Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 5/3
10:40-18:40
2 stops25h 00m
Chicago Midway
Sun 29/3
13:10-07:35
2 stops26h 25m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 5/3
14:15-21:30
2 stops24h 15m
Chicago O'Hare Intl
Sun 29/3
13:57-07:35
2 stops25h 38m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 2/2
11:45-18:52
2 stops24h 07m
Chicago O'Hare Intl
Mon 9/2
14:40-08:45
2 stops25h 05m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 25/1
10:40-21:43
2 stops28h 03m
Chicago O'Hare Intl
Mon 9/2
13:50-08:30
2 stops25h 40m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 19/2
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Thu 26/2
07:15-09:35
2 stops33h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 29/1
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Sun 15/2
20:40-09:35
2 stops43h 55m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 2/2
11:20-14:55
2 stops44h 35m
Chicago O'Hare Intl
Mon 9/2
15:35-09:35
1 stop25h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 16/5
09:55-21:31
2 stops26h 36m
Chicago O'Hare Intl
Sat 6/6
16:40-10:40
2 stops27h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 25/1
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Mon 9/2
07:15-09:35
2 stops33h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 18/2
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Sun 22/2
20:40-09:35
2 stops43h 55m
Booking 82 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.
On average, a flight from Sydney to Chicago takes 21 hours 42 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 Canada and United Airlines.
The cheapest airlines flying from Sydney to Chicago are Qantas Airways, American Airlines and Air Canada.
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).
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
Boarding
Overall
Comfort
Food
Crew
Entertainment
Reviews
Anonymous,Jan 2026
OKA - HND
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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