$638+ Cheap flights to Chicago
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 15/10. Fares are subject to change and may not be available on all flights or dates of travel.
Flights to Chicago in 2025
Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 16 September 2025.
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Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 16 September 2025.
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Use the filters below to find and compare flights to Chicago that are best for you.
Fly from
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 29/10
10:20-08:00
2 stops37h 40m
Chicago O'Hare Intl
Wed 5/11
15:40-09:35
1 stop24h 55m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 6/10
10:20-15:00
1 stop20h 40m
Chicago O'Hare Intl
Thu 25/12
15:40-06:55
1 stop22h 15m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 4/3
11:20-08:05
3 stops37h 45m
Chicago O'Hare Intl
Sat 7/3
12:50-09:35
2 stops27h 45m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 13/10
10:10-13:38
2 stops43h 28m
Chicago Midway
Mon 20/10
05:10-08:05
2 stops34h 55m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Tue 30/9
09:20-07:58
2 stops37h 38m
Chicago O'Hare Intl
Wed 12/11
12:50-09:35
2 stops27h 45m
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Tue 30/9
09:25-17:35
2 stops23h 10m
Chicago Midway
Wed 12/11
12:47-08:30
2 stops26h 43m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 3/12
10:40-08:04
2 stops38h 24m
Chicago O'Hare Intl
Mon 8/12
10:46-08:30
2 stops28h 44m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 4/10
09:30-17:05
2 stops22h 35m
Chicago O'Hare Intl
Tue 23/12
14:17-07:00
1 stop23h 43m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 19/2
12:25-05:16
2 stops33h 51m
Chicago O'Hare Intl
Thu 26/2
16:25-20:15
1 stop34h 50m
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 26/10
10:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Sun 26/10
20:15-08:35
2 stops44h 20m
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Cheapflights Insights
Everything you need to know about your flight to Chicago
When is the best time to book a flight to Chicago?
Use this chart to determine the optimal time to book a return flight from Sydney to Chicago. Price data was last updated on 12 September 2025.
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.
How long is the flight to Chicago?
On average, a flight from Sydney to Chicago takes 21 hours 20 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.
When is the cheapest time to fly to Chicago?
Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 13 October 2024.
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.
What are the most popular airlines that fly to Chicago?
The most popular airlines flying from Sydney to Chicago are Qantas Airways, Air Canada and United Airlines.
What are the cheapest airlines that fly to Chicago?
The cheapest airlines flying from Sydney to Chicago are Qantas Airways, American Airlines and Air Canada.
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
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.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
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).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 16 September 2025.
Get a feel of what it's like to fly with ANA, Air New Zealand, andQantas Airways to the United States by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Anonymous,Aug 2025
SFO - NRT
FAQs about flying to Chicago
Getting around Chicago
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.
Getting downtown from the airport
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.
Travel Tips
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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