Find Cheapest Airlines Flying from Sydney to Chicago
United Airlines
Air Canada
American Airlines Cheap Flight Deals from Sydney to Chicago
Explore the cheapest flights from Sydney to Chicago in the next three months. Based on Trip.com's data from the latest 7 days, one-way fares start at AU$ 934, and round-trip tickets start at AU$ 1,204.
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SYD 11:2020h 21m1 stopORD 14:41Sydney - Chicago | Tue, Feb 3 | Air Canada
ORD 21:1543h 20m1 stopSYD 09:35Chicago - Sydney | Mon, Feb 9 | United AirlinesAU$ 1,204 AU$ 1,99140% off40% offAU$ 1,991 AU$ 1,204 -
SYD 11:2035h 41m1 stopORD 06:01Sydney - Chicago | Tue, Feb 3 | American Airlines
ORD 09:0230h 58m1 stopSYD 09:00Chicago - Sydney | Mon, Feb 9 | American AirlinesAU$ 1,222 AU$ 1,99139% off39% offAU$ 1,991 AU$ 1,222 -
SYD 17:4529h 16m1 stopORD 06:01Sydney - Chicago | Tue, Feb 3 | Qantas Airways
ORD 15:1023h 15m1 stopSYD 07:25Chicago - Sydney | Mon, Feb 9 | American AirlinesAU$ 1,287 AU$ 1,99135% off35% offAU$ 1,991 AU$ 1,287 -
SYD 20:1027h 50m1 stopORD 07:00Sydney - Chicago | Mon, Feb 9 | American Airlines
ORD 15:1522h 40m1 stopSYD 06:55Chicago - Sydney | Sat, Feb 14 | American AirlinesAU$ 1,58720% offAU$ 1,991 AU$ 1,587 -
SYD 11:2020h 30m1 stopORD 14:50Sydney - Chicago | Mon, Feb 9 | United Airlines
ORD 16:0024h 5m1 stopSYD 09:05Chicago - Sydney | Sat, Feb 14 | United AirlinesAU$ 1,59720% offAU$ 1,991 AU$ 1,597 -
SYD 11:2025h 25m1 stopORD 19:45Sydney - Chicago | Thu, Feb 19 | Air Canada
ORD 20:4043h 55m1 stopSYD 09:35Chicago - Sydney | Mon, Feb 23 | Air CanadaAU$ 1,61419% offAU$ 1,991 AU$ 1,614 -
SYD 17:4520h 38m1 stopORD 21:23Sydney - Chicago | Mon, Feb 9 | Qantas Airways
ORD 11:4526h 10m1 stopSYD 06:55Chicago - Sydney | Sat, Feb 14 | American AirlinesAU$ 1,63718% offAU$ 1,991 AU$ 1,637 -
SYD 11:2020h 21m1 stopORD 14:41Sydney - Chicago | Sat, Feb 21 | Air Canada
ORD 15:3525h1 stopSYD 09:35Chicago - Sydney | Mon, Feb 23 | Air CanadaAU$ 1,65717% offAU$ 1,991 AU$ 1,657 -
SYD 11:2020h 30m1 stopORD 14:50Sydney - Chicago | Tue, Feb 3 | Virgin Australia
ORD 18:2921h 46m1 stopSYD 09:15Chicago - Sydney | Mon, Feb 9 | United AirlinesAU$ 1,79310% offAU$ 1,991 AU$ 1,793 -
SYD 11:2020h 21m1 stopORD 14:41Sydney - Chicago | Mon, Jan 26 | Air Canada
ORD 15:4024h 55m1 stopSYD 09:35Chicago - Sydney | Sat, Jan 31 | Air CanadaAU$ 1,8527% offAU$ 1,991 AU$ 1,852 -
SYD 13:0017h 25m1 stopCHI Invalid DateSydney - Chicago | Fri, Jan 23 | Normal Airline
CHI 15:006hDirectSYD 16:00Chicago - Sydney | Sun, Jan 25 | Normal AirlineFind more flightsFind more flights
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SYD 21:4026h 20m1 stopORD 07:00Sydney - Chicago | Fri, Jan 30 | Hawaiian AirlinesAU$ 934 AU$ 1,26826% off26% offAU$ 1,268 AU$ 934 -
SYD 21:4026h 20m1 stopORD 07:00Sydney - Chicago | Fri, Jan 30 | Alaska AirlinesAU$ 941 AU$ 1,26826% off26% offAU$ 1,268 AU$ 941 -
SYD 17:4528h 44m1 stopORD 06:29Sydney - Chicago | Sun, Mar 8 | American AirlinesAU$ 1,080 AU$ 1,26815% off15% offAU$ 1,268 AU$ 1,080 -
SYD 17:4528h 44m1 stopORD 06:29Sydney - Chicago | Sun, Mar 8 | Qantas AirwaysAU$ 1,08515% offAU$ 1,268 AU$ 1,085 -
SYD 11:2035h 18m1 stopORD 05:38Sydney - Chicago | Thu, Feb 19 | American AirlinesAU$ 1,10713% offAU$ 1,268 AU$ 1,107 -
SYD 14:1532h 46m1 stopORD 06:01Sydney - Chicago | Tue, Feb 10 | Delta Air LinesAU$ 1,13910% offAU$ 1,268 AU$ 1,139 -
SYD 11:2020h 21m1 stopORD 14:41Sydney - Chicago | Fri, Jan 30 | Air CanadaAU$ 1,1519% offAU$ 1,268 AU$ 1,151 -
SYD 11:2020h 38m1 stopORD 15:58Sydney - Chicago | Tue, Mar 10 | American AirlinesAU$ 1,1549% offAU$ 1,268 AU$ 1,154 -
SYD 11:2020h 21m1 stopORD 14:41Sydney - Chicago | Tue, Feb 3 | Air CanadaAU$ 1,1668% offAU$ 1,268 AU$ 1,166 -
SYD 10:4021h 18m1 stopORD 15:58Sydney - Chicago | Tue, Mar 10 | Delta Air LinesAU$ 1,1807% offAU$ 1,268 AU$ 1,180 -
SYD 13:0017h 25m1 stopCHI Invalid DateSydney - Chicago | Fri, Jan 23 | Normal AirlineFind more flightsFind more flights
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Displayed flight fares from Sydney to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.
Sydney to Chicago Flight Details
The distance between Sydney and Chicago is approximately 14,881.87km. Based on Trip.com's data travel demand peaks in January. The off-season for travel is October.
| Cheapest one-way flight price | AU$ 934 |
|---|---|
| Cheapest return ticket price | AU$ 1,204 |
| Off-season for travel | October |
| Peak season for travel | January |
| Flight distance | 14,881.87km |
| Popular airline | United Airlines |
Flight FAQs
Which airlines offer the cheapest flights from Sydney (SYD) to Chicago (CHI)?
Based on Trip.com data, Hawaiian Airlines offers one-way fares as low as AU$ 934 on Cheapest nonstop routes (e.g. SYD to ORD on Fri, Jan 30), while Air Canada offers Cheapest nonstop round-trips from AU$ 1,204 departing on Tue, Feb 3 and returning on Mon, Feb 9.Which airlines offer direct flights from Sydney to Chicago?
At the moment, you can catch a direct flight from Sydney to Chicago with the following airlines, including: Qantas Airways Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.When is the best time to book flights from Sydney to Chicago?
By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Sydney to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.How can I find the best deals on flights from Sydney to Chicago?
To find best deals on flights from Sydney to Chicago, you can use various tools on Trip.com:
· Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Fri, Jan 30, with one-way flights priced at just AU$ 934.
· Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Hawaiian Airlines.
· Set up price alerts to easily monitor ticket prices without having to check every day.
· Check Trip.com flight deals and promo codes frequently.
· Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around January.
· Get exclusive promo codes for Trip.com app users.When is the best time to book a flight from Sydney to Chicago to get the best price?
The cheapest months to fly from Sydney to Chicago is October, when demand for travel is lower.Which upcoming date is the cheapest for flights from Sydney to Chicago?
After crunching the numbers on our January flight calendar, it's currently cheapest to fly from Sydney to Chicago on January 27, 2026 with Air Canada, with prices starting at AU$ 1,292.Which airports can I fly through when travelling to Chicago from Sydney?
You can land at any one of the following hubs in Chicago, with Sydney Airport to O'Hare International Airport (SYD-ORD) is by far the most common option on this route: Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).What is the time difference between Sydney and Chicago?
The time difference between Chicago and Sydney is 16h.How can I change or cancel my flight ticket from Sydney to Chicago?
Tickets can only be changed or cancelled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.
Sydney to Chicago by air
If you are travelling from Sydney to Chicago by air or looking for Sydney to Chicago flights, you have come to the right place. Start your search for airfares by giving the travelling date above, or continue reading to find out more about the journey, airlines, flight times, schedules, how to find cheap tickets, and much more.
Sydney to Chicago airfares
The airfares for Sydney and Chicago are subject to fluctuations. The price of an air ticket is influenced by various factors, including the level of demand, the specific travel dates and times selected, seat availability, and the pricing strategies implemented by different airlines. Additionally, the fares may also be adjusted based on the travel class you choose, whether it's first class, business class, or economy class.
How to find cheap flights from Sydney to Chicago
Securing the most affordable deals on flights from Sydney to Chicago requires a combination of flexibility, persistence, and a sprinkle of luck. To assist you in obtaining the best prices, here are some helpful tips:
- 1. Embrace flexibility with your travel dates and times: Airfares tend to be more budget-friendly during early mornings, late evenings, and weekdays.
- 2. Remain open to alternative airports: Exploring nearby airports can often lead to surprisingly lower fares.
- 3. Consider booking separate airlines for outbound and inbound flights: Opting for two one-way tickets instead of a round-trip ticket may potentially offer cost savings.
- 4. Explore the option of booking a connection flight from Sydney to Chicago: Connecting flights can sometimes be more economical than direct ones.
- 5. Keep an eye out for last-minute flight deals: Sometimes, spontaneous travel plans can lead to fantastic bargains.
Airlines from Sydney to Chicago
Regrettably, direct flights from Sydney to Chicago are not available. Nevertheless, Qantas Airways and Virgin Australia offers convenient connecting flight options, allowing passengers to reach Chicago from Sydney with ease.
Sydney to Chicago flight time
In the absence of a non-stop Sydney to Chicago flight, the flight time can vary due to connecting flights and layovers. The duration of the layover depends on factors like baggage reclaim and whether the connecting flights depart from the same or different airports. These variables impact the overall travel duration, possibly causing deviations from the estimated timeframe. Verify flight details on the booking page for accurate information.
Everything you need to know about Sydney airport
Sydney Airport (SYD) is Australia's busiest airport, with three main terminals: Terminal 1 for international flights, Terminal 2 for domestic flights, and Terminal 3 for Qantas flights. It offers a comprehensive range of flight routes connecting Sydney to destinations across the globe. Traveling between the airport and the city center is convenient, with options including trains, buses, rideshare and taxis. The train ride takes approximately 13 minutes, while buses and taxis can take around 20-30 minutes, depending on traffic conditions.
Arriving at Chicago airport
O'Hare International Airport (ORD), commonly referred to as Chicago Airport, is a major aviation hub in the United States. It comprises four main terminals: Terminal 1, Terminal 2, Terminal 3, and Terminal 5. The airport offers a wide range of flight routes, connecting Chicago to numerous domestic and international destinations. Traveling from the airport to the city center is convenient, with the Chicago Transit Authority (CTA) Blue Line train providing a direct 45-minute journey. Taxis and ride-sharing services are also readily available, with travel times ranging from 30 to 45 minutes, depending on traffic conditions.
Book Sydney to Chicago flights on Trip.com to unlock extra benefits
Trip.com not only helps you find the cheap airfares from Sydney to Chicago, but also provide extra perks and benefits. When you make your flight reservation, you unlock a world of discounts on hotels, car rentals, and airport transfers, allowing you to save more on your journey. As a token of our appreciation, Trip.com rewards you with Tripcoins through our loyalty program, which can be redeemed for additional benefits on your future trips.
Trip.com Airline Insights on Flights from Sydney toChicago
Which airlines offer the cheapest nonstop flights from Sydney to Chicago?
Based on Trip.com data from the past 12 months, Qantas Airways offers the cheapest nonstop flights from Sydney to Chicago, with an average price of AU$ 888.