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Cheap flights from Sydney to Chicago from $772

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 23/8. Fares are subject to change and may not be available on all flights or dates of travel.
SYD — CHI
18 Jun — 25 Jun1
1 adult

Cheapflights Tip: The best prices from Sydney Kingsford Smith to Chicago are usually found in March or May, booked 87 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 June 2025.

Round-trip from

$1,606

One-way from

$772

Popular in

December

Cheapest in

March

Average price

$1,669
14/8-4/9
  • 14/8-4/9
  • 4 total stops
  • 63h 26m total
  • Sydney to Chicago
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23/8
  • 23/8
  • 2 total stops
  • 24h 21m total
  • Sydney to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($588 potential increase over avg. return price).
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Cheapest flight prices on average. 5% potential price decrease ($123 potential savings vs. average return price).
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Average for round-trip flights in June 2025
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Find flight deals from Sydney to Chicago

Cheapest flights from Sydney to Chicago
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 June 2025.

Thu 14/813:15SYD - ORD
2 stops24h 31mMultiple Airlines
Thu 4/906:20ORD - SYD
2 stops38h 55mMultiple Airlines
Deal found 12/6$1,606
Mon 21/709:25SYD - MDW
2 stops23h 37mDelta
Sun 17/810:11MDW - SYD
2 stops29h 24mDelta
Deal found 12/6$1,678
Mon 21/709:25SYD - ORD
2 stops25h 02mDelta
Sun 17/815:50ORD - SYD
2 stops23h 45mDelta
Deal found 12/6$1,678
Fri 13/620:55SYD - ORD
1 stop26h 45mANA
Thu 31/709:05ORD - SYD
2 stops43h 10mANA
Deal found 12/6$1,686
Mon 4/809:10SYD - ORD
1 stop23h 32mAmerican Airlines
Mon 25/806:00ORD - SYD
1 stop34h 05mAmerican Airlines
Deal found 12/6$1,733
Wed 23/708:55SYD - ORD
2 stops29h 48mJapan Airlines
Tue 19/801:30ORD - SYD
1 stop37h 50mJapan Airlines
Deal found 12/6$1,868
Thu 17/709:10SYD - ORD
1 stop21h 34mBritish Airways
Mon 28/722:17ORD - SYD
1 stop41h 48mBritish Airways
Deal found 9/6$1,891
Wed 8/1010:20SYD - ORD
2 stops27h 47mAir Canada
Thu 16/1008:55ORD - SYD
2 stops31h 25mAir Canada
Deal found 10/6$1,957
Thu 12/607:40SYD - ORD
1 stop45h 45mCathay Pacific
Wed 25/616:00ORD - SYD
1 stop27h 50mCathay Pacific
Deal found 11/6$2,109
Thu 25/1211:20SYD - ORD
1 stop26h 02mUnited Airlines
Fri 23/112:45ORD - SYD
1 stop24h 35mUnited Airlines
Deal found 10/6$2,165
Sat 19/721:40SYD - ORD
2 stops47h 00mAlaska Airlines
Wed 30/706:00ORD - SYD
2 stops46h 45mAlaska Airlines
Deal found 11/6$2,244
Sat 19/720:30SYD - MDW
2 stops28h 15mWestJet
Mon 28/709:24MDW - SYD
2 stops30h 11mWestJet
Deal found 12/6$11,777

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 June 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

Thu 14/8

13:15-22:46

2 stops24h 31m

Chicago O'Hare Intl

Thu 4/9

06:20-12:15

2 stops38h 55m

$1,606

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 21/7

09:25-18:02

2 stops23h 37m

Chicago Midway

Sun 17/8

10:11-06:35

2 stops29h 24m

$1,678

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 21/7

09:25-19:27

2 stops25h 02m

Chicago O'Hare Intl

Sun 17/8

15:50-06:35

2 stops23h 45m

$1,678

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/8

20:55-08:40

1 stop26h 45m

Chicago O'Hare Intl

Mon 25/8

20:20-19:15

2 stops31h 55m

$1,712

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Mon 4/8

09:10-17:42

1 stop23h 32m

Chicago O'Hare Intl

Mon 25/8

06:00-07:05

1 stop34h 05m

$1,733

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 23/7

08:55-23:43

2 stops29h 48m

Chicago O'Hare Intl

Tue 19/8

01:30-06:20

1 stop37h 50m

$1,868

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Thu 31/7

09:20-07:59

2 stops37h 39m

Chicago O'Hare Intl

Thu 7/8

08:45-07:20

2 stops31h 35m

$1,970

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 19/7

14:05-14:25

1 stop39h 20m

Chicago O'Hare Intl

Wed 30/7

16:00-10:50

1 stop27h 50m

$2,088

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Sat 19/7

21:40-05:40

2 stops47h 00m

Chicago O'Hare Intl

Wed 30/7

06:00-19:45

2 stops46h 45m

$2,244

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Wed 25/6

09:30-04:51

1 stop34h 21m

Chicago O'Hare Intl

Mon 4/8

07:10-07:00

1 stop32h 50m

$2,541

Flights are sorted by cheapest return flights first.

Deals found on 11/6

Showing 1-10 of 22 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 9 June 2025.

Booking 87 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 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 June 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 10% on flights from Sydney to Chicago by exploring options for tickets in the afternoon.

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 13 October 2024.

Travellers seeking maximum savings on their Sydney to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Tuesday at midday flights should be avoided if possible as fares are typically the most expensive at this time.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 June 2025.
To help decide which airline to fly from Sydney to Chicago, see what other customers have to say about Air Tahiti Nui, Korean Air and Japan Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Air Tahiti Nui
8.7
Very Good
64 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Korean Air
8.4
Very Good
1,091 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Japan Airlines
8.3
Very Good
1,490 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
ANA
8.3
Very Good
882 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Delta
8.0
Very Good
7,946 reviews
Air Tahiti Nui
8.7
Very Good
64 reviews
Check prices

Overall

8.7

Entertainment

7.3

Comfort

8.1

Food

7.8

Boarding

8.7

Crew

9.0

Reviews

1 / 2
10.0
Excellent

Isabelle,Apr 2023

AKL - PPT

Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.

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.

  • What are the cheapest airlines flying from Sydney to Chicago round-trip?

    Cheapflights users have booked flights from Sydney to Chicago round-trip from $1,678. Other airlines that can offer you cheap pricing are ANA, from $1,712, and American Airlines, from $1,733.

  • What are the cheapest airlines to fly from Sydney to Chicago one-way?

    To fly one-way, consider booking your trip with American Airlines, which is currently one of the cheapest options available, starting at $1,174. Delta flights start at $1,423 while deals on Air Tahiti Nui start at $1,795 one-way.

  • Can I find deals for flights from Sydney to Chicago that include hotel bookings?

    Yes. In addition to deals on Sydney to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Sydney to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sydney to Chicago.

  • 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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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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 June 2025.
Qantas Airways flights from Sydney Kingsford Smith to Chicago
Air Canada flights from Sydney Kingsford Smith to Chicago
ANA flights from Sydney Kingsford Smith to Chicago

Top 6 airlines flying from Sydney to Chicago

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 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Qantas AirwaysCheapest$1,016Average$1,277FlexibilityNo cancel feeOn-time74%
Search Qantas Airways flights
American AirlinesCheapest$1,197Average$1,602FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Air CanadaCheapest$1,277Average$1,717FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
ANACheapest$1,612Average$1,810FlexibilityNo cancel feeOn-time80%
Search ANA flights
United AirlinesCheapest$1,695Average$2,469FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Virgin AustraliaCheapest$1,769Average$2,797FlexibilityNo cancel feeOn-time80%
Search Virgin Australia flights

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How does Cheapflights help users find flights from Sydney to Chicago?

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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.

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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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