SYD - CHI

$549 Find Cheap Flights from Sydney to Chicago – Compare and Save

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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

Wed, 4 Nov - Mon, 9 Nov
Air Canada Logo
11:20 - 14:37SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 17m1 stop Vancouver Intl
Air Canada Logo
08:49 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 46m1 stop Vancouver Intl
$1,354Air Canada
Wed, 4 Nov - Mon, 9 Nov
Air Canada Logo
11:20 - 19:58SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 38m2 stops Vancouver Intl Toronto Pearson Intl
Air Canada Logo
15:30 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 05m1 stop Vancouver Intl
$1,365Air Canada
Mon, 19 Oct - Mon, 26 Oct
Multiple Airlines Logo
14:15 - 05:16SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
31h 01m3 stops Nadi Los Angeles Los Angeles Las Vegas Harry Reid Intl
Multiple Airlines Logo
06:30 - 12:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
38h 05m3 stops Denver Intl Los Angeles Los Angeles Nadi
$1,402Multiple Airlines
Thu, 5 Nov - Mon, 9 Nov
Multiple Airlines Logo
14:00 - 05:13SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
32h 13m3 stops Nadi Los Angeles Los Angeles Las Vegas Harry Reid Intl
Multiple Airlines Logo
06:30 - 12:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
37h 05m3 stops Denver Intl Los Angeles Los Angeles Nadi
$1,440Multiple Airlines
Wed, 4 Nov - Mon, 9 Nov
Air New Zealand Logo
11:50 - 21:45SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 55m2 stops Auckland Intl San Francisco
Air New Zealand Logo
09:21 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 14m2 stops Houston George Bush Intcntl Auckland Intl
$1,755Air New Zealand
Wed, 4 Nov - Mon, 9 Nov
Air New Zealand Logo
11:50 - 21:45SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
26h 55m2 stops Auckland Intl San Francisco
Air New Zealand Logo
09:21 - 08:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 14m2 stops Houston George Bush Intcntl Auckland Intl
$1,761Air New Zealand
Wed, 4 Nov - Mon, 9 Nov
American Airlines Logo
20:30 - 10:05SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 35m2 stops Honolulu Dallas/Fort Worth
American Airlines Logo
06:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
33h 31m1 stop Los Angeles Los Angeles
$1,836American Airlines
Wed, 4 Nov - Tue, 10 Nov
American Airlines Logo
20:30 - 12:24SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
32h 54m2 stops Honolulu Dallas/Fort Worth
American Airlines Logo
05:30 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 30m1 stop Los Angeles Los Angeles
$1,840American Airlines
Mon, 12 Oct - Mon, 26 Oct
Qantas Airways Logo
13:00 - 18:35SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 35m1 stop Dallas/Fort Worth
Qantas Airways Logo
08:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
32h 31m1 stop Los Angeles Los Angeles
$1,893Qantas Airways
Mon, 12 Oct - Sun, 25 Oct
Qantas Airways Logo
13:00 - 19:16SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 16m1 stop Dallas/Fort Worth
Qantas Airways Logo
08:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
32h 31m1 stop Los Angeles Los Angeles
$1,929Qantas Airways
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 from Sydney to Chicago with more confidence.

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 $1,724 return. Other Sydney to Chicago routes average $2,142, based on KAYAK data over the past 12 months.

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

Wednesday is the cheapest day of the week to fly from Sydney to Chicago and is 9% cheaper than the average day. Monday is the most expensive day with flight prices 14% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • September is the cheapest month to fly from Sydney to Chicago at $1,369 return.
  • July ($1,944) and December ($1,891) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 42% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are prices from Sydney to Chicago the cheapest?

Flights from Sydney to Chicago are cheapest 20 weeks before departure. Booking in this window typically costs about 10% 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

$549
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly (13% more expensive on average)
Flights 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 route details based on KAYAK data, including flight times, airports, airlines, and booking questions.

  • 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 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

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

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

    • Los Angeles Los Angeles (LAX) – 62% of one-stop connections
    • Vancouver Intl (YVR) – 21% of one-stop connections
    • San Francisco (SFO) – 12% of one-stop connections
    • Dallas/Fort Worth (DFW) – 3% of one-stop connections

    Los Angeles Los Angeles (LAX) handles the largest share of one-stop connections on this route.

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

    Yes. Being flexible with your travel dates can save you up to 21% on the Sydney to Chicago route. Wednesday is the cheapest departure day at $1,574 return on average, while Monday is the most expensive at $1,973, a difference of $399. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago?

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

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

    Last-minute fares on this route (booked within 2 weeks of departure) run 9% below the route average of $1,726. Booking late can sometimes save money on this route, but inventory is limited.

  • How long is a flight from Sydney to Chicago?

    A direct flight from Sydney to Chicago takes 0h 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 are flight prices from Sydney to Chicago looking right now?

    One-way fares from Sydney to Chicago are currently lower than usual. Average one-way flight prices are about $1,170, which is 9% below the typical average for this route.

  • 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 50m, compared to 21h 02m via San Francisco (SFO) and 21h 13m via Los Angeles Los Angeles (LAX).

  • What is the time difference between Sydney and Chicago?

    Chicago is 15 hours behind Sydney (Central Time vs Eastern Australia Time). Plan for the time shift when scheduling connections or first-day activities.

  • 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
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) – daily rates from around $45:

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

    Near Chicago Greater Rockford Airport (RFD) – daily rates from around $42:

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

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

    Return flights from Sydney to Chicago range from $1,470 to $2,090, with an average of $1,726 over the past 12 months. Anything below $1,470 counts as a good deal.

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 Wednesday departure instead of Monday. On this route, Wednesday flights average $1,574 – about $399 less than Monday (20% 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 10% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Sydney to Chicago trip for September. Fares historically average $1,369 return in that month – typically $575 less than the most expensive month, which is July (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