Find Cheapest Airlines Flying from Sydney to Chicago

Choose from 3 carriers that fly from Sydney to Chicago, including United Airlines, Air Canada, and American Airlines. Enjoy the cheapest tickets on this route with Hawaiian Airlines.
United Airlines logo United Airlines
Air Canada logo Air Canada
American Airlines logo American Airlines
Airlines are determined based on actual purchased flight tickets from Sydney to Chicago according to previous 12 months data from Trip.com.

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.

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 priceAU$ 934
Cheapest return ticket priceAU$ 1,204
Off-season for travelOctober
Peak season for travelJanuary
Flight distance14,881.87km
Popular airlineUnited Airlines
Flight statistics for the Sydney–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

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.
  • 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.
  • 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.
  • 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.
  • The cheapest months to fly from Sydney to Chicago is October, when demand for travel is lower.
  • 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.
  • 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).
  • The time difference between Chicago and Sydney is 16h.
  • 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?

Data is based on the average price of all nonstop flights from Sydney to Chicago on Trip.com in the past 12 months.

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.

AU$ 564
AU$ 888
AU$ 1,213
AU$ 1,538
AU$ 1,862
Qantas Airways
AU$ 888
Qantas Airways
Etihad Airways
AU$ 1,014
Etihad Airways
Air Canada
AU$ 1,435
Air Canada
American Airlines
AU$ 1,493
American Airlines
Cathay Pacific
AU$ 1,506
Cathay Pacific
United Airlines
AU$ 1,862
United Airlines