SYD - CHI

$618 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
$1,053
Typical prices: $1,549-$2,290
American Airlines
Sun 18/2Thu 22/2
SYD - ORD • 1 stop
Cheapest one-way flight
$618
Typical prices: $1,075-$1,710
Delta
Fri 2/2
SYD - ORD • 1 stop
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.
Insights
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 $1,667 (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

Thu, 18 Feb - Mon, 22 Feb
American Airlines Logo
11:20 - 22:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 35m1 stop Los Angeles
American Airlines Logo
18:46 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 14m1 stop Los Angeles
$1,053American Airlines
Mon, 26 Apr - Sat, 8 May
Delta Logo
09:15 - 16:37SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 22m2 stops Los Angeles Atlanta Hartsfield-Jackson
Delta Logo
17:55 - 06:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
45h 55m2 stops Atlanta Hartsfield-Jackson Los Angeles
$1,059Delta
Mon, 16 Nov - Mon, 30 Nov
Delta Logo
10:40 - 23:55SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 15m1 stop Los Angeles
Delta Logo
07:45 - 08:30ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 45m1 stop Los Angeles
$1,059Delta
Mon, 16 Nov - Mon, 30 Nov
Qantas Airways Logo
11:10 - 16:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 55m1 stop Los Angeles
Qantas Airways Logo
21:03 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 57m1 stop Los Angeles
$1,085Qantas Airways
Thu, 18 Feb - Mon, 22 Feb
Qantas Airways Logo
14:05 - 14:18SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
41h 13m1 stop Dallas/Fort Worth
Qantas Airways Logo
16:59 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
23h 01m1 stop Los Angeles
$1,099Qantas Airways
Thu, 26 Nov - Thu, 3 Dec
Multiple Airlines Logo
11:15 - 16:42SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 27m1 stop Los Angeles
Multiple Airlines Logo
17:15 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 45m1 stop Los Angeles
$1,120Multiple Airlines
Sat, 26 Dec - Tue, 19 Jan
American Airlines Logo
11:10 - 23:40SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
29h 30m2 stops Los Angeles Phoenix Sky Harbor Intl
American Airlines Logo
06:00 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 00m1 stop Los Angeles
$1,123American Airlines
Thu, 18 Feb - Mon, 22 Feb
Cathay Pacific Logo
08:45 - 12:30SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
44h 45m1 stop Hong Kong Intl
Cathay Pacific Logo
14:10 - 20:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
37h 40m1 stop Hong Kong Intl
$1,845Cathay Pacific
Mon, 1 Feb - Sat, 20 Feb
Air New Zealand Logo
07:30 - 20:38SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 08m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
14:25 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 10m2 stops San Francisco Auckland Intl
$1,874Air New Zealand
Fri, 20 Nov - Sat, 5 Dec
Air New Zealand Logo
14:05 - 00:59SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 54m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
12:55 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
28h 40m2 stops Los Angeles Auckland Intl
$1,921Air New Zealand
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 $1,549 to $2,290. The lowest price found in the past 5 days was $1,053 on American 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 $1,861 return. Other Sydney to Chicago routes average $2,215, 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 $1,553 return.
•December ($2,421) and September ($2,112) 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

$618
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 $1,549 to $2,290, with an average of $1,864 over the past 12 months. Anything below $1,549 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 $1,864 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 $1,445.

  • 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 $120:

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

    Near Chicago Greater Rockford Airport (RFD) – daily rates averaging $117:

    • 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 $1,719 return on average, while Saturday is the most expensive at $2,121, a difference of $401.

    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 $1,719, about $401 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 $1,553 return in that month – typically $868 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 Chicago Midway Airport

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