SYD - CHI

$562 Find Cheap Flights from Sydney to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$927
Typical prices: $1,061-$1,508
Air Canada
Sun 10/28Sat 11/24
SYD - ORD • 1 stop
Cheapest one-way
$562
Typical prices: $794-$1,092
Multiple Airlines
Fri 2/23
SYD - ORD • 3 stops
Nonstop 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 • 11% average savings
SYD - MDW
Most popular
Insights
Insights
When to book
20 weeks
in advance
Our data shows that travelers who book at least 20 weeks in advance save around 10% compared to booking last minute.
Insights
Insights
When to travel
September
Cheapest • 21% price drop
July
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $1,141 (round-trip)
San Francisco (SFO)
Shortest trip • 21h 02m (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 round-trip flight deals from Sydney to Chicago

Wed, Oct 28 - Tue, Nov 24
Air Canada Logo
10:20 am - 8:01 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 41m1 stop Vancouver Intl
Air Canada Logo
10:37 am - 9:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 58m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$927Air Canada
Wed, Oct 28 - Tue, Nov 24
Air Canada Logo
10:20 am - 7:52 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 32m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
10:37 am - 9:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 58m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$929Air Canada
Mon, Oct 5 - Mon, Oct 19
Air Canada Logo
10:20 am - 8:06 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 46m1 stop Vancouver Intl
Air Canada Logo
3:40 pm - 8:20 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 40m1 stop Vancouver Intl
$929Air Canada
Mon, Oct 5 - Mon, Oct 19
Air Canada Logo
10:20 am - 2:43 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 23m1 stop Vancouver Intl
Air Canada Logo
11:05 am - 8:20 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 15m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$931Air Canada
Mon, Oct 5 - Mon, Oct 19
Air Canada Logo
10:20 am - 8:12 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 52m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
11:05 am - 8:20 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 15m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$933Air Canada
Thu, Oct 1 - Mon, Oct 26
Air Canada Logo
9:20 am - 4:45 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 25m1 stop Vancouver Intl
Air Canada Logo
8:49 am - 8:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 46m1 stop Vancouver Intl
$944Air Canada
Tue, Oct 27 - Thu, Nov 12
Air Canada Logo
10:20 am - 2:37 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 17m1 stop Vancouver Intl
Air Canada Logo
3:30 pm - 9:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 05m1 stop Vancouver Intl
$944Air Canada
Thu, Oct 1 - Mon, Oct 26
Air Canada Logo
9:20 am - 2:43 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 23m1 stop Vancouver Intl
Air Canada Logo
1:55 pm - 8:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
26h 40m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$946Air Canada
Tue, Dec 1 - Tue, Jan 26
Qantas Airways Logo
11:10 am - 5:59 amSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 49m1 stop Los Angeles Los Angeles
Qantas Airways Logo
3:06 pm - 6:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 29m1 stop Las Vegas Harry Reid Intl
$1,520Qantas Airways
Tue, Dec 1 - Tue, Jan 26
Qantas Airways Logo
11:10 am - 5:59 amSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
35h 49m1 stop Los Angeles Los Angeles
Qantas Airways Logo
3:06 pm - 6:35 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
22h 29m1 stop Las Vegas Harry Reid Intl
$1,522Qantas 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.

How much is a round-trip flight from Sydney to Chicago?

Round-trip flights from Sydney to Chicago start at $927. Prices are below average for this route right now, with typical round-trip fares ranging from $1,061 to $1,508. The lowest price found in the past 5 days was $927 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 $1,244 round-trip. Other Sydney to Chicago routes average $1,546, 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, it 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 $988 round-trip.
  • July ($1,403) and December ($1,365) 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

$562
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 13% increase in price.
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 round-trip 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).

  • What 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
    • First 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 $1,136 round-trip on average, while Monday is the most expensive at $1,424, a difference of $288. 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 Magnificent Mile, Grant Park and River North. 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 $1,246. Booking late can sometimes save money on this route, but inventory is limited.

  • How long is a flight from Sydney to Chicago?

    A nonstop flight from Sydney to Chicago takes 0h 00m, covering 9,241 miles.

  • 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 $851, which is 8% below the typical average for this route.

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

    Flying via Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time at 20h 50m, compared with 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 rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

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

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

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

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

    Round-trip flights from Sydney to Chicago range from $1,061 to $1,508, with an average of $1,246 over the past 12 months. Anything below $1,061 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 can be flexible, aim for a Wednesday departure instead of Monday. On this route, Wednesday flights average $1,136 - about $288 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 $988 round-trip in that month - typically $415 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
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from Sydney to Chicago

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

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago