SYD - CHI

$735 Find Cheap Flights from Sydney to Chicago – Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return flight
$1,411
Typical prices: $1,568-$2,318
Air Canada
Sun 21/1Sun 28/1
SYD - ORD • 1 stop
Cheapest one-way flight
$735
Typical prices: $1,088-$1,731
Multiple Airlines
Mon 5/3
SYD - ORD • 2 stops
Direct flights
Not available
There are currently no direct flights between Sydney and Chicago. You'll need to take a connecting flight to reach the destination.
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Top routes
SYD - ORD
Cheapest • 9% average savings
SYD - MDW
Most popular
Insights
Insights
When to book
20 weeks
in advance
Our data shows that travellers who book at least 20 weeks in advance save around 32% compared to booking last minute.
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Insights
When to travel
October
Cheapest • 17% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top stopover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $1,688 (return)
Houston George Bush Intcntl (IAH)
Shortest trip • 21h 06m (one-way)
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Insights
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Flight Deals

Cheap Flights from Sydney to Chicago (SYD-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Sydney to Chicago

Thu, 21 Jan - Thu, 28 Jan
Air Canada Logo
11:20 - 14:32SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 12m1 stop Vancouver Intl
Air Canada Logo
13:55 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$1,411Air Canada
1 day ago
Thu, 21 Jan - Thu, 28 Jan
Air Canada Logo
11:20 - 14:32SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 12m1 stop Vancouver Intl
Air Canada Logo
15:35 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 00m1 stop Vancouver Intl
$1,414Air Canada
1 day ago
Wed, 20 Jan - Tue, 9 Feb
Air New Zealand Logo
14:05 - 20:40SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 35m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
14:33 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 02m2 stops San Francisco Auckland Intl
$1,845Air New Zealand
3+ days ago
Thu, 1 Apr - Mon, 10 May
Philippine Airlines Logo
11:35 - 17:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 20m1 stop Manila Ninoy Aquino Intl
Philippine Airlines Logo
23:45 - 09:45ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
43h 00m1 stop Manila Ninoy Aquino Intl
$1,925Philippine Airlines
2 days ago
Thu, 18 Feb - Thu, 24 Jun
Cathay Pacific Logo
08:45 - 12:30SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
44h 45m1 stop Hong Kong Intl
Cathay Pacific Logo
16:00 - 06:10ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
47h 10m1 stop Hong Kong Intl
$2,067Cathay Pacific
22 hours ago
Wed, 20 Jan - Tue, 9 Feb
Qantas Airways Logo
21:25 - 16:54SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
36h 29m1 stop San Francisco
Qantas Airways Logo
16:55 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
23h 05m1 stop Los Angeles
$2,138Qantas Airways
3+ days ago
Thu, 26 Nov - Thu, 3 Dec
Qantas Airways Logo
11:10 - 15:16SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 06m1 stop Los Angeles
Qantas Airways Logo
06:49 - 06:55ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 06m2 stops Cincinnati Cinci./N. Kentucky Dallas/Fort Worth
$2,484Qantas Airways
2 days ago
Thu, 26 Nov - Fri, 11 Dec
Air New Zealand Logo
14:05 - 05:01SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
31h 56m2 stops Auckland Intl Honolulu
Air New Zealand Logo
14:22 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
27h 13m2 stops Houston George Bush Intcntl Auckland Intl
$2,531Air New Zealand
3+ days ago
Mon, 7 Dec - Thu, 31 Dec
Delta Logo
10:40 - 21:56SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 16m2 stops Los Angeles Salt Lake City
Delta Logo
06:00 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
33h 30m2 stops Atlanta Hartsfield-Jackson Los Angeles
$2,850Delta
2 days ago
Mon, 7 Dec - Thu, 31 Dec
Delta Logo
10:40 - 23:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 19m1 stop Los Angeles
Delta Logo
07:59 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 31m1 stop Los Angeles
$2,850Delta
2 days ago
Booking Insights

Price, demand, and travel trends for Sydney to Chicago flights

Use KAYAK data on prices, travel dates, airlines, and seasonal trends to compare options and book flights with more confidence.

How much is a return flight from Sydney to Chicago?

Return flights from Sydney to Chicago typically range from $1,568 to $2,318. The lowest price found in the past 5 days was $1,411 on Air Canada.

What is the cheapest Sydney to Chicago flight route?

Sydney (SYD) to Chicago O'Hare Intl Airport (ORD) is the cheapest Sydney to Chicago route, averaging $1,884 return. Other Sydney to Chicago routes average $2,242, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Sydney to Chicago?

Based on deals KAYAK users found in the last 12 months, Sunday is the cheapest day of the week to fly from Sydney to Chicago. It's 8% cheaper than the average day, while Saturday is the most expensive, with prices 13% higher.

What is the cheapest month to fly from Sydney to Chicago?

•October is the cheapest month to fly from Sydney to Chicago at $1,572 return.
•December ($2,451) and September ($2,138) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 55% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Sydney to Chicago the cheapest?

Flights from Sydney to Chicago are cheapest 20 weeks before departure. Booking in this window typically costs about 32% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Key details for Sydney to Chicago flights

Low season

April

Cheapest flight

$735
Beat the crowds with an average 51% drop in travellers.
The most popular month to fly with an average 99% increase in travellers.
One-way flight from Sydney to Chicago O'Hare Intl Airport

When to book flights from Sydney to Chicago

Are your dates flexible? Find out the best times to travel from Sydney to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

Your Sydney to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines, and booking tips.

  • Which cabin classes can I book on flights from Sydney to Chicago?

    Three cabin classes are available on flights from Sydney to Chicago:

    • Economy class
    • Premium Economy Class
    • Business Class

  • How long is a flight from Sydney to Chicago?

    A direct flight from Sydney to Chicago takes 00m, covering 23,934 km.

  • Do I need a passport to fly from Sydney to Chicago?

    Yes, a valid passport is required for this international route. Many destinations require at least six months of validity beyond your travel dates. Check your passport expiry well before booking.

  • How much should I expect to pay for a Sydney to Chicago flight?

    Return flights from Sydney to Chicago range from $1,568 to $2,318, with an average of $1,887 over the past 12 months. Anything below $1,568 counts as a good deal.

  • How expensive are last-minute Sydney to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 15% above the $1,887 route average. Book 20 weeks before departure for the lowest fares.

  • Have flight prices from Sydney to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, return flight prices on this route showed a wide range, from about $1,411 to $9,799. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Sydney to Chicago looking right now?

    One-way fares from Sydney to Chicago are currently higher than usual. Average one-way flight prices are about $1,615, which is 13% above the typical average for this route.

  • What car hire options are available in Chicago?

    Since Chicago is served by multiple airports, car hire options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) – daily rates averaging $91:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) – daily rates averaging $124:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) – daily rates averaging $118:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Sydney to Chicago?

    Flights from Sydney to Chicago usually depart from Sydney Kingsford Smith (SYD) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Sydney to Chicago pass through?

    One-stop flights from Sydney to Chicago most commonly connect through:

    • Los Angeles (LAX) – 67% of one-stop connections
    • Vancouver Intl (YVR) – 14% of one-stop connections
    • San Francisco (SFO) – 8% of one-stop connections
    • Dallas/Fort Worth (DFW) – 3% of one-stop connections

  • Can I save money by using flexible dates for flights from Sydney to Chicago?

    Yes. Flexible dates can save you up to 19% on flights from Sydney to Chicago. Sunday is the cheapest departure day at $1,740 return on average, while Saturday is the most expensive at $2,146, a difference of $406.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • How much time can I save by choosing a different stopover airport from Sydney to Chicago?

    Flying via Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time of 20h 53m, compared to 21h 06m via Houston George Bush Intcntl (IAH) and 21h 37m via Los Angeles (LAX).

  • What is the time difference between Sydney and Chicago?

    Chicago is 17 hours behind Sydney (Central Time vs Eastern Australia Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are River North, Millennium Park, and Chicago Water Tower. These are among the most viewed places in Chicago on KAYAK.

Your guide to booking Sydney to Chicago flights

Get tips on when to book, when to fly, and what to know before your trip.
  • If your dates are flexible, aim for a Sunday departure and avoid flying on Saturday. On this route, Sunday flights average $1,740, about $406 less than Saturday fares (19% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 20 weeks before you fly. On this route, that window historically saves about 32% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Sydney to Chicago trip for October. Fares historically average $1,572 return in that month – typically $879 less than the most expensive month, which is December (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Skylark Motel

More options for your flight from Sydney to Chicago

Complete your trip to Chicago with a hotel stay or car hire

Car hire in Chicago
Hotels in Chicago
Holidays in Chicago