SYD - CHI

$649 Find Cheap Flights from Sydney to Chicago – Compare and Save

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Everything you should know

Cheapest return flight
$1,429
Typical prices: $1,555-$2,304
Philippine Airlines
Fri 2/2Mon 5/3
SYD - ORD • 1 stop
Cheapest one-way flight
$633
Typical prices: $1,132-$1,656
Multiple Airlines
Fri 16/2
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 30% compared to booking last minute.
Insights
Insights
When to travel
October
Cheapest • 19% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top stopover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $1,604 (return)
Houston George Bush Intcntl (IAH)
Shortest trip • 21h 06m (one-way)
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Insights
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We hope you enjoy your trip to Chicago!
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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

Tue, 2 Feb - Fri, 5 Mar
Philippine Airlines Logo
11:30 - 16:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 25m1 stop Manila Ninoy Aquino Intl
Philippine Airlines Logo
22:45 - 09:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 05m1 stop Manila Ninoy Aquino Intl
$1,429Philippine Airlines
Tue, 2 Feb - Wed, 10 Feb
Philippine Airlines Logo
11:30 - 16:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 25m1 stop Manila Ninoy Aquino Intl
Philippine Airlines Logo
22:45 - 09:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 05m1 stop Manila Ninoy Aquino Intl
$1,584Philippine Airlines
Tue, 19 Jan - Tue, 26 Jan
Air New Zealand Logo
09:55 - 20:03SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 08m2 stops Auckland Intl Houston George Bush Intcntl
Air New Zealand Logo
12:40 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
28h 55m2 stops Houston George Bush Intcntl Auckland Intl
$1,787Air New Zealand
Thu, 28 Jan - Tue, 9 Feb
Air New Zealand Logo
14:05 - 20:38SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
23h 33m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
10:42 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 53m2 stops San Francisco Auckland Intl
$1,787Air New Zealand
Fri, 25 Dec - Thu, 31 Dec
Air Canada Logo
11:20 - 20:40SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 20m3 stops Vancouver Intl Saskatoon Toronto Pearson Intl
Air Canada Logo
13:47 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 48m1 stop Toronto Pearson Intl
$1,818Air Canada
Mon, 23 Nov - Mon, 30 Nov
American Airlines Logo
11:10 - 00:13SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 03m1 stop Los Angeles
American Airlines Logo
15:17 - 06:55ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 38m2 stops Moline Quad-City Dallas/Fort Worth
$1,972American Airlines
Fri, 25 Dec - Thu, 31 Dec
Air Canada Logo
11:20 - 14:37SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 17m1 stop Vancouver Intl
Air Canada Logo
10:33 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 02m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$2,157Air Canada
Fri, 15 Jan - Tue, 26 Jan
Qantas Airways Logo
11:20 - 15:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 39m1 stop Los Angeles
Qantas Airways Logo
18:45 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 15m1 stop Los Angeles
$2,514Qantas Airways
Mon, 14 Dec - Wed, 30 Dec
Qantas Airways Logo
11:10 - 16:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 49m1 stop Los Angeles
Qantas Airways Logo
15:55 - 06:55ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 00m1 stop Dallas/Fort Worth
$2,843Qantas Airways
Thu, 24 Dec - Mon, 11 Jan
American Airlines Logo
11:10 - 00:19SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 09m1 stop Los Angeles
American Airlines Logo
20:57 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
43h 03m1 stop Los Angeles
$2,896American Airlines
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 $1,555 to $2,304. The lowest price found in the past 5 days was $1,429 on Philippine Airlines.

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 $1,853 return. Other Sydney to Chicago routes average $2,200, 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 6% cheaper than the average day, while Monday is the most expensive, with prices 12% higher.

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

•October is the cheapest month to fly from Sydney to Chicago at $1,513 return.
•December ($2,260) and September ($2,090) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 49% 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 30% 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

February

Cheapest flight

$633
Beat the crowds with an average 49% drop in travellers.
The most popular month to fly with an average 83% 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 $1,555 to $2,304, with an average of $1,856 over the past 12 months. Anything below $1,555 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 12% above the $1,856 route average. Book 20 weeks before departure for the lowest fares.

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

    One-way fares from Sydney to Chicago are currently in line with typical prices for this route. Average one-way fares are about $1,440.

  • 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 from around $24:

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

    Near Chicago Midway Airport (MDW) – daily rates from around $46:

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

    Near Chicago Greater Rockford Airport (RFD) – daily rates from around $40:

    • 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) – 65% of one-stop connections
    • Vancouver Intl (YVR) – 16% of one-stop connections
    • San Francisco (SFO) – 10% 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 17% on flights from Sydney to Chicago. Sunday is the cheapest departure day at $1,747 return on average, while Monday is the most expensive at $2,090, a difference of $343.

    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 43m, compared to 21h 06m via Houston George Bush Intcntl (IAH) and 21h 12m via Los Angeles (LAX).

  • What is the time difference between Sydney and Chicago?

    Chicago is 16 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 Monday. On this route, Sunday flights average $1,747, about $343 less than Monday fares (16% 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 30% 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 $1,513 return in that month – typically $747 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