Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 29/5
11:55-00:58
2 stops28h 03m
Chicago O'Hare Intl
Fri 5/6
16:40-10:40
2 stops27h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 5/2
11:20-19:45
2 stops25h 25m
Chicago O'Hare Intl
Sun 8/2
20:40-09:35
2 stops43h 55m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 23/3
10:25-14:41
1 stop20h 16m
Chicago O'Hare Intl
Tue 28/4
15:40-07:20
1 stop24h 40m
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
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 3/2
10:40-17:29
2 stops23h 49m
Chicago Midway
Wed 18/2
13:49-08:30
2 stops25h 41m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 24/3
11:50-17:05
1 stop21h 15m
Chicago O'Hare Intl
Tue 28/4
16:00-07:00
1 stop24h 00m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 24/3
12:10-18:52
1 stop22h 42m
Chicago O'Hare Intl
Wed 29/4
16:40-06:55
1 stop23h 15m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 24/3
13:15-23:59
2 stops26h 44m
Chicago O'Hare Intl
Wed 29/4
15:54-06:35
2 stops23h 41m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 25/3
10:25-17:02
2 stops22h 37m
Chicago O'Hare Intl
Sat 2/5
21:20-06:55
1 stop42h 35m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 26/3
12:10-18:54
2 stops22h 44m
Chicago O'Hare Intl
Wed 29/4
16:40-06:55
1 stop23h 15m
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 47 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).
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
CGK - HND
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
CGK - HND
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
CGK - HND
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
CGK - HND
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
CGK - HND
Entertainment
Boarding
Comfort
Crew
Overall
Food
Reviews
Lindsey,Jan 2026
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.
Cheapflights helps you find that perfect flight to Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Certainly. Search results for flights to Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
Of course! You can track prices for flights to Chicago and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals to set up your price alerts.