CA $615 Cheap Flights from Sydney (SYD) to Chicago (ORD)

You can find one-way and return flights from SYD to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when SYD to ORD ticket fares go up or down.

The cheapest months to fly from SYD to ORD are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.

Enter SYD to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

To find a cheap flight from Sydney, NSW (SYD) to Chicago, IL (ORD), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

There are around 57 connecting flights per day from Sydney, NSW (SYD-Kingsford Smith Intl.) to Chicago, IL (ORD-O'Hare Intl.). Some common connection points include Vancouver Intl. (YVR), Los Angeles Intl. (LAX), and Auckland Intl. (AKL).

The earliest flight from Sydney, NSW (SYD-Kingsford Smith Intl.) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 6:00 AM. This service is operated by Emirates and runs year-round, meaning you can find this early flight option throughout January, February, March, April, May, June, July, August, September, October, November, and December. An early departure like this can be great for maximising your time in Chicago, allowing you to arrive and start your day without delay. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from Sydney, NSW (SYD-Kingsford Smith Intl.) to Chicago, IL (ORD-O'Hare Intl.) on a Monday, with around 29 flights available. This gives you a good selection for your travel plans. Major airlines on this route include Qantas Airways, United, and Air New Zealand. Looking at the week, Monday offers notably more flight options compared to other days, with about 29 flights, while Wednesday has fewer, around 9 flights.

The most popular departure times for flights from Sydney, NSW (SYD-Kingsford Smith Intl.) to Chicago, IL (ORD-O'Hare Intl.) are in the morning, from 9am to 12pm. Many major carriers, including United, American Airlines and Delta, offer flights during this window. Many travellers prefer this because it allows for an early start to their journey.

There are no nonstop flights from Sydney, NSW (SYD-Kingsford Smith Intl.) to Chicago, IL (ORD-O'Hare Intl.). For flights with one stop, you can expect the journey to take around 22 hours 30 minutes. If your flight has two or more stops, the travel time typically increases to about 24 hours 30 minutes. This route covers a significant distance of approximately 14,864 kilometres. Keep in mind that actual flight times can vary due to factors like layover duration, specific routing, and even wind patterns.

You can fly business class or first class between SYD and ORD.

Airlines that offer business class service on this route include:

• Qatar Airways
• Korean Air
• Air New Zealand
• Turkish Airlines
• Etihad Airways
• Alaska Airlines
• Asiana Airlines
• Air India
• Air Canada
• Cathay Pacific
• Air Japan Company
• Emirates
• Japan Airlines
• All Nippon Airways
• Qantas Airways
• United
• American Airlines

First class cabins are available on:

• Emirates
• Japan Airlines
• Qantas Airways
• American Airlines

It's easy to earn miles on a Sydney, NSW (SYD) to Chicago, IL (ORD) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

If you're planning to travel to Chicago from Kingsford Smith Intl. (SYD), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Los Angeles Intl. (LAX), San Francisco Intl. (SFO), or Vancouver Intl. (YVR) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Sydney, NSW (SYD) to Chicago, IL (ORD) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Sydney, NSW (SYD) to Chicago, IL (ORD) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Sydney, NSW (SYD) to Chicago, IL (ORD) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.