Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 16/5
11:55-23:28
2 stops26h 33m
Chicago O'Hare Intl
Sat 6/6
15:51-08:45
2 stops25h 54m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 25/12
14:00-17:04
1 stop20h 04m
Chicago O'Hare Intl
Fri 23/1
19:58-06:20
1 stop41h 22m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 19/2
12:10-14:45
1 stop19h 35m
Chicago O'Hare Intl
Fri 6/3
14:26-09:05
2 stops25h 39m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 20/2
14:00-22:52
2 stops25h 52m
Chicago O'Hare Intl
Fri 6/3
18:20-09:05
1 stop21h 45m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 11/5
11:50-05:05
2 stops32h 15m
Chicago O'Hare Intl
Mon 8/6
17:45-19:15
1 stop34h 30m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 6/2
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Fri 13/2
14:00-09:35
2 stops26h 35m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 11/5
09:15-18:05
2 stops23h 50m
Chicago Midway
Mon 8/6
13:05-06:35
2 stops26h 30m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 16/5
09:10-15:56
1 stop21h 46m
Chicago O'Hare Intl
Sat 6/6
18:45-07:05
1 stop21h 20m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 19/2
10:40-22:42
2 stops29h 02m
Chicago Midway
Fri 6/3
13:28-08:30
2 stops26h 02m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Fri 20/2
10:40-17:45
2 stops24h 05m
Chicago Midway
Fri 6/3
13:28-08:30
2 stops26h 02m
Booking 52 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 41 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
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
Comfort
Crew
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
Comfort
Crew
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
Comfort
Crew
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
Comfort
Crew
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
Comfort
Crew
Boarding
Overall
Food
Entertainment
Reviews
Mario,Nov 2025
HND - BKK
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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