Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 5/3
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Wed 18/3
07:15-08:35
2 stops33h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 9/3
11:20-11:18
2 stops39h 58m
Chicago O'Hare Intl
Tue 24/3
07:15-08:35
2 stops33h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 19/3
10:25-08:00
2 stops37h 35m
Chicago O'Hare Intl
Tue 21/4
08:42-07:20
2 stops31h 38m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 9/3
11:20-13:01
2 stops41h 41m
Chicago O'Hare Intl
Wed 11/3
15:35-08:35
1 stop25h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 20/3
10:20-08:00
2 stops37h 40m
Chicago O'Hare Intl
Mon 23/3
07:15-08:35
3 stops33h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 2/7
06:30-05:47
2 stops38h 17m
Chicago O'Hare Intl
Tue 21/7
07:08-07:20
2 stops33h 12m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 19/3
09:40-17:54
2 stops24h 14m
Chicago Midway
Tue 21/4
12:52-06:50
2 stops26h 58m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 14/7
09:15-18:05
2 stops23h 50m
Chicago Midway
Wed 22/7
13:00-06:50
2 stops26h 50m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Wed 15/7
09:15-18:05
2 stops23h 50m
Chicago Midway
Wed 22/7
13:00-06:50
2 stops26h 50m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 3/3
10:40-18:40
2 stops25h 00m
Chicago Midway
Wed 11/3
13:10-07:25
2 stops26h 15m
Booking 87 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 38 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, Air Canada 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).
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Boarding
Entertainment
Overall
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
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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