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Flights from Sydney to Chicago

Find cheap airlines flights from Sydney to Chicago

You can choose from 1 airlines that fly from Sydney to Chicago, including Philippine Airlines, Delta Air Lines has lowest fares on this route.
Philippine Airlines logo Philippine Airlines
Airlines are determined based on actual purchased flight tickets from Sydney to Chicago according to previous 12 months data from Trip.com.

Find flight deals from Sydney to Chicago for the next 3 months. Book one way flights from $608 or round trip flights from $1,091.

      • SYD 9:10 AM
        34h 50m
        1 stop
        ORD 5:00 AM
        Sydney - Chicago | Thu, Aug 6 | American Airlines
        ORD 7:00 AM
        33h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Mon, Aug 10 | American Airlines
        $1,091 $1,563
        30% off
        30% off
        $1,563 $1,091
      • SYD 9:10 AM
        28h 50m
        1 stop
        ORD 11:00 PM
        Sydney - Chicago | Thu, Jul 30 | Qantas Airways
        ORD 10:00 AM
        30h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Wed, Aug 5 | American Airlines
        $1,108 $1,563
        28% off
        28% off
        $1,563 $1,108
      • SYD 9:10 AM
        29h 57m
        1 stop
        ORD 12:07 AM
        Sydney - Chicago | Wed, Jul 22 | American Airlines
        ORD 8:10 AM
        31h 55m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Wed, Jul 29 | American Airlines
        $1,127 $1,563
        28% off
        28% off
        $1,563 $1,127
      • SYD 9:10 AM
        30h 19m
        1 stop
        ORD 12:29 AM
        Sydney - Chicago | Thu, Aug 6 | Qantas Airways
        ORD 7:00 AM
        33h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Mon, Aug 10 | American Airlines
        $1,132
        28% off
        $1,563 $1,132
      • SYD 9:10 AM
        29h 57m
        1 stop
        ORD 12:07 AM
        Sydney - Chicago | Tue, Aug 4 | American Airlines
        ORD 6:00 AM
        34h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Sun, Aug 9 | American Airlines
        $1,167
        25% off
        $1,563 $1,167
      • SYD 9:10 AM
        29h 57m
        1 stop
        ORD 12:07 AM
        Sydney - Chicago | Wed, Jul 22 | Qantas Airways
        ORD 6:00 AM
        34h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Wed, Jul 29 | American Airlines
        $1,173
        25% off
        $1,563 $1,173
      • SYD 9:10 AM
        30h 10m
        1 stop
        MDW 12:20 AM
        Sydney - Chicago | Thu, Jul 23 | American Airlines
        MDW 5:30 AM
        34h 35m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Wed, Jul 29 |
        $1,177
        25% off
        $1,563 $1,177
      • SYD 9:10 AM
        29h 57m
        1 stop
        ORD 12:07 AM
        Sydney - Chicago | Tue, Aug 4 | Qantas Airways
        ORD 7:00 AM
        33h 5m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Sun, Aug 9 | American Airlines
        $1,213
        22% off
        $1,563 $1,213
      • SYD 9:10 AM
        30h 10m
        1 stop
        MDW 12:20 AM
        Sydney - Chicago | Thu, Jul 23 | Qantas Airways
        MDW 5:30 AM
        34h 35m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Wed, Jul 29 |
        $1,223
        22% off
        $1,563 $1,223
      • SYD 12:00 PM
        21h 16m
        1 stop
        ORD 6:16 PM
        Sydney - Chicago | Thu, Jul 16 | American Airlines
        ORD 8:49 PM
        43h 16m
        1 stop
        SYD 7:05 AM
        Chicago - Sydney | Mon, Jul 20 | American Airlines
        $1,234
        21% off
        $1,563 $1,234
      • SYD 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Sydney - Chicago | Sat, Jun 20 | Normal Airline
        CHI 3:00 PM
        6h
        Nonstop
        SYD 4:00 PM
        Chicago - Sydney | Mon, Jun 22 | Normal Airline
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      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Thu, Jul 30 | Delta Air Lines
        $608 $847
        28% off
        28% off
        $847 $608
      • SYD 9:15 AM
        30h 14m
        1 stop
        ORD 12:29 AM
        Sydney - Chicago | Wed, Aug 5 | Delta Air Lines
        $610 $847
        28% off
        28% off
        $847 $610
      • SYD 9:10 AM
        36h 7m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Tue, Jul 28 | American Airlines
        $616 $847
        27% off
        27% off
        $847 $616
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Tue, Jul 28 | Delta Air Lines
        $627
        26% off
        $847 $627
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Sat, Aug 1 | Delta Air Lines
        $631
        26% off
        $847 $631
      • SYD 9:10 AM
        36h 7m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Mon, Jul 27 | American Airlines
        $654
        23% off
        $847 $654
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Wed, Jul 8 | Delta Air Lines
        $659
        22% off
        $847 $659
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Sat, Aug 15 | Delta Air Lines
        $660
        22% off
        $847 $660
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Thu, Jul 16 | Delta Air Lines
        $664
        22% off
        $847 $664
      • SYD 9:15 AM
        36h 2m
        1 stop
        ORD 6:17 AM
        Sydney - Chicago | Tue, Jul 7 | Delta Air Lines
        $669
        21% off
        $847 $669
      • SYD 1:00 PM
        17h 25m
        1 stop
        CHI 2:00 PM
        Sydney - Chicago | Sat, Jun 20 | Normal Airline
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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.

Flight Info | Sydney to Chicago

The distance between Sydney and Chicago is approximately 14,881.87 km. Based on Trip.com's data travel demand peaks in January. The off-season for travel is October.

Cheapest one-way flight price$608
Cheapest round-trip ticket price$1,091
Off-season for travelOctober
Peak season for travelJanuary
Flight distance14,881.87 km
Popular airlinePhilippine Airlines
Flight statistics for the Sydney–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Frequently Asked Questions

  • What are the cheapest flights from Sydney to Chicago (SYD-CHI)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as $608 on Cheapest nonstop routes (e.g. SYD to ORD on Thu, Jul 30), while American Airlines offers Cheapest nonstop round-trips from $1,091 departing on Thu, Aug 6 and returning on Mon, Aug 10.
  • At the moment, several airlines serve connecting flights from Sydney to Chicago, including: Philippine Airlines Selected airlines are based on historical data collected from flight bookings made by users 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 Thu, Jul 30, with one-way flights priced at just $608.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Delta Air Lines.
    · 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 June flight calendar, it's currently cheapest to fly from Sydney to Chicago on June 24, 2026 with Delta Air Lines, with prices starting at $731.
  • You can land at any one of the following hubs in Chicago, with Sydney Airport to Chicago O'Hare International Airport (SYD-ORD) is by far the most common option on this route: Chicago O'Hare International Airport (ORD) Chicago Midway International Airport (MDW) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Sydney is 16h.
  • Tickets can only be changed or canceled 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.

Explore More Popular Flights

Note: Prices shown on this page are estimated lowest price and include all taxes and fees found in the last 24 hours.

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 24 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
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.
Cancellation/change due to a flight schedule change:
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.