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 26/11. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
13 Dec — 20 Dec1
Return
1 adult
Economy
Return
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or May, booked 82 days in advance, depart on a Tuesday or Monday and return on a Sunday
Cheap flight deals from Sydney to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Sydney (SYD) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 13 November 2025.
Explore the most affordable flight options available from Sydney to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 13 November 2025.
Mon 1/1211:20SYD - ORD
1 stop21h 48mAmerican Airlines
Tue 16/1211:45ORD - SYD
1 stop28h 15mAmerican Airlines
Deal found 11/11$1,559
Thu 13/1112:25SYD - ORD
1 stop42h 25mANA
Wed 26/1118:00ORD - SYD
2 stops33h 15mANA
Deal found 12/11$1,714
Sat 15/1109:55SYD - ORD
2 stops25h 55mAir New Zealand
Mon 29/1212:50ORD - SYD
2 stops30h 50mAir New Zealand
Deal found 11/11$1,946
Thu 13/1111:20SYD - ORD
1 stop20h 21mAir Canada
Wed 26/1115:40ORD - SYD
1 stop24h 55mAir Canada
Deal found 12/11$1,992
Sun 16/1111:20SYD - ORD
1 stop20h 21mAir Canada
Wed 19/1115:40ORD - SYD
1 stop24h 55mAir Canada
Deal found 10/11$2,127
Sat 15/1111:20SYD - ORD
1 stop20h 21mAir Canada
Mon 29/1220:15ORD - SYD
2 stops44h 20mAir Canada
Deal found 11/11$2,147
Sun 16/1115:15SYD - ORD
1 stop38h 40mCathay Pacific
Wed 19/1114:35ORD - SYD
1 stop26h 00mCathay Pacific
Deal found 10/11$2,186
Wed 17/1214:05SYD - ORD
1 stop20h 07mAmerican Airlines
Thu 22/111:56ORD - SYD
1 stop25h 59mAmerican Airlines
Deal found 11/11$2,196
Thu 13/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 26/1113:15MDW - SYD
2 stops26h 15mDelta
Deal found 12/11$2,520
Fri 26/1210:40SYD - MDW
2 stops23h 39mDelta
Fri 2/106:00MDW - SYD
2 stops33h 30mDelta
Deal found 11/11$2,522
Fri 14/1110:40SYD - MDW
2 stops24h 38mDelta
Thu 27/1110:47MDW - SYD
2 stops28h 43mDelta
Deal found 12/11$2,670
Sun 16/1110:40SYD - MDW
2 stops22h 58mDelta
Thu 20/1113:15MDW - SYD
2 stops26h 15mDelta
Deal found 11/11$2,671
Best flights from Sydney to Chicago
Discover carefully curated flight deals from Sydney to Chicago that have cost, travel time, and stopovers in mind to ensure you get the best travel experience. Data last updated 13 November 2025.
Mon 1/1211:20SYD - ORD
1 stop23h 25mAmerican Airlines
Tue 16/1215:05ORD - SYD
2 stops24h 55mAmerican Airlines
Deal found 11/11$1,559
Mon 2/209:55SYD - ORD
2 stops25h 57mAir New Zealand
Thu 19/214:35ORD - SYD
2 stops25h 10mAir New Zealand
Deal found 11/11$1,804
Mon 2/211:20SYD - ORD
1 stop22h 22mAir Canada
Sun 8/215:40ORD - SYD
1 stop24h 55mAir Canada
Deal found 11/11$1,962
Thu 12/219:00SYD - ORD
2 stops41h 35mMultiple Airlines
Tue 5/500:30ORD - SYD
2 stops40h 10mMultiple Airlines
Deal found 11/11$2,007
Mon 2/212:25SYD - ORD
2 stops33h 50mANA
Sun 8/216:25ORD - SYD
1 stop34h 50mANA
Deal found 11/11$2,075
Mon 2/210:40SYD - MDW
2 stops23h 52mDelta
Thu 19/212:46MDW - SYD
2 stops26h 44mDelta
Deal found 11/11$2,147
Thu 12/209:55SYD - ORD
2 stops27h 28mAir New Zealand
Wed 6/516:17ORD - SYD
2 stops27h 18mAir New Zealand
Deal found 11/11$1,902
Sat 7/311:20SYD - ORD
2 stops25h 10mAir Canada
Thu 12/307:15ORD - SYD
3 stops33h 20mAir Canada
Deal found 11/11$1,971
Thu 19/211:20SYD - ORD
1 stop20h 21mAir Canada
Mon 2/315:40ORD - SYD
1 stop24h 55mAir Canada
Deal found 12/11$1,972
Thu 19/214:15SYD - MDW
2 stops25h 29mDelta
Mon 2/309:34MDW - SYD
2 stops29h 56mDelta
Deal found 12/11$2,297
Sun 1/211:20SYD - ORD
1 stop20h 21mAir Canada
Sat 9/518:30ORD - SYD
2 stops45h 50mAir Canada
Deal found 12/11$2,040
Wed 10/1210:40SYD - MDW
2 stops30h 07mDelta
Mon 15/1209:34MDW - SYD
2 stops29h 56mDelta
Deal found 12/11$2,520
Mon 2/210:40SYD - MDW
2 stops24h 15mDelta
Sun 8/213:28MDW - SYD
2 stops26h 02mDelta
Deal found 11/11$2,520
Fri 26/1210:40SYD - MDW
2 stops22h 40mDelta
Fri 2/109:50MDW - SYD
2 stops29h 40mDelta
Deal found 11/11$2,522
Fri 26/1206:20SYD - MDW
2 stops31h 25mMultiple Airlines
Fri 2/108:00MDW - SYD
1 stop29h 55mMultiple Airlines
Deal found 11/11$4,101
Fri 12/1210:40SYD - MDW
2 stops24h 38mDelta
Sat 10/109:34MDW - SYD
2 stops28h 16mDelta
Deal found 12/11$3,157
Mon 15/1210:40SYD - MDW
2 stops30h 07mDelta
Thu 15/113:28MDW - SYD
2 stops26h 02mDelta
Deal found 11/11$3,231
Sun 14/1210:40SYD - MDW
2 stops30h 07mDelta
Fri 2/109:50MDW - SYD
2 stops29h 40mDelta
Deal found 12/11$3,479
Tue 25/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 24/1211:48MDW - SYD
2 stops27h 42mDelta
Deal found 11/11$4,093
Last-minute flights from Sydney to Chicago
Discover last-minute flight deals from Sydney to Chicago. Data last updated 13 November 2025 and is based on user searches.
Thu 13/1112:25SYD - ORD
1 stop42h 25mANA
Wed 26/1118:00ORD - SYD
2 stops33h 15mANA
Deal found 12/11$1,714
Thu 13/1111:20SYD - ORD
1 stop20h 21mAir Canada
Wed 26/1115:40ORD - SYD
1 stop24h 55mAir Canada
Deal found 12/11$1,992
Thu 13/1110:40SYD - MDW
2 stops24h 38mDelta
Wed 26/1113:15MDW - SYD
2 stops26h 15mDelta
Deal found 12/11$2,520
Fri 14/1111:20SYD - ORD
1 stop20h 21mAir Canada
Thu 27/1107:05ORD - SYD
2 stops33h 30mAir Canada
Deal found 12/11$2,056
Sat 15/1109:55SYD - ORD
2 stops25h 55mAir New Zealand
Mon 29/1212:50ORD - SYD
2 stops30h 50mAir New Zealand
Deal found 11/11$1,946
Sat 15/1111:20SYD - ORD
1 stop20h 21mAir Canada
Mon 29/1220:15ORD - SYD
2 stops44h 20mAir Canada
Deal found 11/11$2,147
Sun 16/1110:40SYD - MDW
2 stops22h 58mDelta
Wed 19/1113:47MDW - SYD
2 stops25h 43mDelta
Deal found 10/11$2,584
Sun 16/1110:40SYD - MDW
2 stops22h 58mDelta
Thu 20/1113:15MDW - SYD
2 stops26h 15mDelta
Deal found 11/11$2,671
Mon 1/1211:20SYD - ORD
1 stop21h 48mAmerican Airlines
Tue 16/1211:45ORD - SYD
1 stop28h 15mAmerican Airlines
Deal found 11/11$1,559
Wed 17/1214:05SYD - ORD
1 stop20h 07mAmerican Airlines
Thu 22/111:56ORD - SYD
1 stop25h 59mAmerican Airlines
Deal found 11/11$2,196
Thu 18/1211:20SYD - ORD
1 stop22h 31mAmerican Airlines
Thu 22/115:23ORD - SYD
1 stop22h 32mAmerican Airlines
Deal found 11/11$2,258
Fri 26/1210:40SYD - MDW
2 stops22h 40mDelta
Fri 2/109:50MDW - SYD
2 stops29h 40mDelta
Deal found 11/11$2,522
One-way flights from Sydney to Chicago
Search for one-way flight options from Sydney to Chicago. Find affordable one-way fares based on user searches. Data last updated 13 November 2025.
Wed 26/1111:45SYD - ORD
2 stops24h 45mAir New Zealand
Deal found 11/11$936
Thu 7/511:50SYD - ORD
2 stops25h 52mAir New Zealand
Deal found 11/11$944
Wed 11/211:45SYD - ORD
2 stops25h 04mAir New Zealand
Deal found 11/11$976
Wed 3/1213:55SYD - ORD
2 stops22h 49mAir New Zealand
Deal found 11/11$978
Thu 5/317:00SYD - ORD
3 stops47h 56mMultiple Airlines
Deal found 11/11$985
Wed 3/1214:15SYD - ORD
3 stops50h 58mMultiple Airlines
Deal found 11/11$1,002
Wed 11/217:00SYD - ORD
3 stops47h 35mMultiple Airlines
Deal found 11/11$1,019
Sun 7/1206:20SYD - ORD
3 stops34h 53mMultiple Airlines
Deal found 11/11$1,039
Tue 2/1207:05SYD - ORD
3 stops40h 20mMultiple Airlines
Deal found 11/11$1,083
Mon 1/1219:15SYD - ORD
3 stops52h 10mMultiple Airlines
Deal found 11/11$1,105
Sun 7/1206:20SYD - MDW
3 stops56h 58mMultiple Airlines
Deal found 11/11$1,118
Thu 5/310:20SYD - MDW
3 stops44h 39mMultiple Airlines
Deal found 11/11$1,167
Cheapflights Fare Finder
Customise your flight search to find flights from Sydney to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 13 November 2025.
Use the filters below to find and compare flights from Sydney to Chicago that are best for you.
Fly from
Sydney
Fly to
Chicago
Route
Depart
Return
Price
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 1/12
11:20-17:45
1 stop23h 25m
Chicago O'Hare Intl
Tue 16/12
15:05-09:00
2 stops24h 55m
$1,559
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 2/2
09:55-18:52
2 stops25h 57m
Chicago O'Hare Intl
Thu 19/2
14:35-08:45
2 stops25h 10m
$1,804
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 12/2
09:55-20:23
2 stops27h 28m
Chicago O'Hare Intl
Wed 6/5
16:17-10:35
2 stops27h 18m
$1,902
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 2/2
11:20-16:42
1 stop22h 22m
Chicago O'Hare Intl
Sun 8/2
15:40-09:35
1 stop24h 55m
$1,962
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sat 7/3
11:20-19:30
2 stops25h 10m
Chicago O'Hare Intl
Thu 12/3
07:15-08:35
3 stops33h 20m
$1,971
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 19/2
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Mon 2/3
15:40-09:35
1 stop24h 55m
$1,972
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 12/2
19:00-19:35
2 stops41h 35m
Chicago O'Hare Intl
Tue 5/5
00:30-07:40
2 stops40h 10m
$2,007
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Sun 1/2
11:20-14:41
1 stop20h 21m
Chicago O'Hare Intl
Sat 9/5
18:30-07:20
2 stops45h 50m
$2,040
SydneyChicago
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 2/2
12:25-05:15
2 stops33h 50m
Chicago O'Hare Intl
Sun 8/2
16:25-20:15
1 stop34h 50m
$2,075
SydneyChicago
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Mon 2/2
10:40-17:32
2 stops23h 52m
Chicago Midway
Thu 19/2
12:46-08:30
2 stops26h 44m
$2,147
Flights are sorted by cheapest return flights first.
Deals found on 11/11
Showing 1-10 of 37 results
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Best time to book a flight from Sydney to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Sydney with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Sydney to Chicago
How far ahead should I book a flight from Sydney 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 7 November 2025.
Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Sydney to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $949). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,599). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SYD to CHI?
Find hourly flight availability from Sydney to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 13 November 2025.
Unlike in the morning, when flights are generally more expensive, you can save up to 21% on flights from Sydney to Chicago by exploring options for tickets in the evening.
What is the cheapest day to fly from Sydney to Chicago?
Use this chart to determine the cheapest time to fly return from Sydney to Chicago. Price data was last updated on 16 December 2024.
Travellers seeking maximum savings on their Sydney to Chicago flight should consider departing on Monday at midday when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
What’s the top stopover airport for flights from Sydney to Chicago?
Share of one-stop return flights from Sydney to Chicago chosen by Cheapflights users in the past 12 months, using the same stopover each way.
Los Angeles (LAX) – chosen by Cheapflights users on 73% of one-stop itineraries from Sydney to Chicago on Cheapflights.
What’s the cheapest stopover airport for flights from Sydney to Chicago?
Average return fare for one-stop flights from Sydney to Chicago, chosen by Cheapflights users in the past 12 months, with the same stopover each way.
Los Angeles (LAX) is the most affordable one-stop option, with an average return flight price of $1,555.
What’s the fastest stopover option from Sydney to Chicago?
Shortest average travel time for one-stop one-way flights from Sydney to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by stopover airport.
Flights via San Francisco (SFO) have the shortest average one-way travel time for one-stop routes: 19h 35m.
Which airport typically offers the quickest stopover for flights from Sydney to Chicago?
Average stopover duration for one-stop one-way flights from Sydney to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.
Flights via San Francisco (SFO) offer the fastest connection on this route, with an average stopover time of 1h 35m.
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 13 November 2025.
See what other customers who have flown with ANA, Air New Zealand, andQantas Airways from Sydney to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Flight attendants are nice, friendly and helpful. Highly recommend to flight with this airline.
Related info for your journey
Find useful and relevant information for your journey from Sydney to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
What airport do you fly from for flights from Sydney to Chicago?
For a flight from Sydney to Chicago, you will be flying from Kingsford Smith. Sydney Kingsford Smith (SYD) is just 7.5 km from the centre of the city. Kingsford Smith is the only Sydney airport and it handles 0 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Sydney Kingsford Smith on a regular basis.
How long is the flight from Sydney to Chicago?
Airlines like American Airlines, Air New Zealand, and Air Canada fly from Sydney to Chicago in about 22h 22m. The time it takes to get you to your destination can typically vary by up to 3h 35m. The distance between Sydney and Chicago is about 14851 km. Both multi-stop and direct flights can be found to your destination and back.
What are the cheapest airlines flying from Sydney to Chicago round-trip?
Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,006. Other airlines that can offer you cheap pricing are American Airlines, from $1,193, and Air Canada, from $1,196. You may be able to fly from Sydney to Chicago for 33% less than the average price by searching for these airlines.
Can I find deals for business class flights from Sydney to Chicago?
Yes. Cheapflights offers flight deals from Sydney to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Sydney to Chicago?
Currently, September is the cheapest month in which you can book a flight from Sydney to Chicago (average of $949). Flying from Sydney to Chicago in December is currently the most expensive (average of $1,599). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Fly from Sydney to Chicago on these airlines
Choose from the following airlines for your flight from Sydney to Chicago. Flights are based on user searches made on Cheapflights and were last updated on 13 November 2025.
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on 13 November 2025.
Discover the top 6 airlines that operate flights from Sydney to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 647,157 searches. Data last updated 13 November 2025.
Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.
How does Cheapflights help users find flights from Sydney to Chicago?
Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Sydney to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.
Why should you use Cheapflights to find cheap flight tickets from Sydney to Chicago?
By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Sydney.
Can Cheapflights find flights from Sydney to Chicago with no change fees?
Users can book flights with no change fees policies with our dedicated filters. Book flights from Sydney to Chicago flexibly with Cheapflights today.
Can Cheapflights notify me if prices for flights from Sydney to Chicago become cheaper?
Of course! You can now track prices for flights from Sydney 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 above to set up your price alerts.
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