Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 16/5
11:50-22:42
2 stops25h 52m
Chicago O'Hare Intl
Sat 6/6
16:40-08:45
2 stops25h 05m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 12/5
09:25-18:05
2 stops23h 40m
Chicago Midway
Tue 2/6
14:00-06:35
2 stops25h 35m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 11/5
09:25-18:31
2 stops24h 06m
Chicago Midway
Mon 1/6
14:00-06:35
2 stops25h 35m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 14/5
09:25-19:43
2 stops25h 18m
Chicago O'Hare Intl
Mon 1/6
15:50-06:35
2 stops23h 45m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 13/5
09:25-18:01
2 stops23h 36m
Chicago O'Hare Intl
Wed 3/6
12:15-06:35
2 stops27h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 11/5
09:25-16:36
2 stops22h 11m
Chicago O'Hare Intl
Tue 2/6
12:15-06:35
2 stops27h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 13/5
09:25-16:36
2 stops22h 11m
Chicago O'Hare Intl
Sun 31/5
09:30-06:35
2 stops30h 05m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 12/5
09:25-18:41
2 stops24h 16m
Chicago O'Hare Intl
Wed 3/6
12:15-06:35
2 stops27h 20m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 14/5
09:25-21:52
2 stops27h 27m
Chicago O'Hare Intl
Sun 31/5
15:50-06:35
2 stops23h 45m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Sun 10/5
09:25-18:05
2 stops23h 40m
Chicago Midway
Sun 31/5
14:00-06:35
2 stops25h 35m
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 22 hours 52 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.
Users looking for the lowest fares to Chicago should consider flying on Monday at midday, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday evenings, when prices are usually at their highest.
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).
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - HND
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - HND
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - HND
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - HND
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - HND
Comfort
Crew
Overall
Entertainment
Boarding
Food
Reviews
Julie,Sept 2025
CGK - 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.
Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.
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