Fly from
Route
Depart
Return
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 19/5
09:15-21:09
2 stops26h 54m
Chicago Midway
Tue 26/5
13:22-06:50
2 stops26h 28m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 21/4
09:15-19:52
2 stops25h 37m
Chicago O'Hare Intl
Wed 6/5
14:09-06:50
2 stops25h 41m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 23/6
10:20-23:16
2 stops27h 56m
Chicago O'Hare Intl
Tue 30/6
12:40-07:00
2 stops27h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 24/6
08:55-07:45
1 stop37h 50m
Chicago O'Hare Intl
Fri 3/7
14:30-06:20
1 stop24h 50m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Sun 17/5
09:15-21:09
2 stops26h 54m
Chicago Midway
Sun 24/5
13:59-06:50
2 stops25h 51m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 21/6
09:15-23:18
1 stop29h 03m
Chicago O'Hare Intl
Sun 19/7
11:30-06:50
2 stops28h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 12/6
09:10-15:52
1 stop21h 42m
Chicago O'Hare Intl
Wed 15/7
15:21-07:05
1 stop24h 44m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Fri 26/6
09:15-08:37
2 stops38h 22m
Chicago Midway
Mon 29/6
13:49-06:50
2 stops26h 01m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 26/6
09:15-11:44
2 stops41h 29m
Chicago O'Hare Intl
Fri 3/7
18:15-06:50
1 stop21h 35m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 9/6
09:15-18:31
2 stops24h 16m
Chicago Midway
Mon 15/6
13:16-06:50
2 stops26h 34m
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 22 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 Air Canada, American Airlines and Qantas Airways.
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).
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Overall
Boarding
Entertainment
Crew
Comfort
Food
Reviews
Anonymous,Feb 2026
BKK - NRT
Overall
Boarding
Entertainment
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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