SYD - CHI

$431 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 round-trip
$735
Typical prices: $1,081-$1,598
American Airlines
Sun 2/18Thu 2/22
SYD - ORD • 1 stop
Cheapest one-way
$431
Typical prices: $750-$1,194
Delta
Fri 2/2
SYD - ORD • 1 stop
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 • 9% 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 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 layover airports
Dallas/Fort Worth (DFW)
Cheapest • Avg $1,164 (round-trip)
Houston George Bush Intcntl (IAH)
Shortest trip • 21h 06m (one-way)
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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

Thu, Feb 18 - Mon, Feb 22
American Airlines Logo
11:20 am - 10:55 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
28h 35m1 stop Los Angeles
American Airlines Logo
6:46 pm - 9:00 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
21h 14m1 stop Los Angeles
$735American Airlines
Mon, Nov 16 - Mon, Nov 30
Delta Logo
10:40 am - 11:55 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 15m1 stop Los Angeles
Delta Logo
7:45 am - 8:30 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 45m1 stop Los Angeles
$739Delta
Mon, Apr 26 - Sat, May 8
Delta Logo
9:15 am - 4:37 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
46h 22m2 stops Los Angeles Atlanta Hartsfield-Jackson
Delta Logo
5:55 pm - 6:50 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
45h 55m2 stops Atlanta Hartsfield-Jackson Los Angeles
$739Delta
Wed, Jan 20 - Sun, Jan 31
Delta Logo
10:40 am - 5:53 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
24h 13m1 stop Los Angeles
Delta Logo
7:25 am - 6:50 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
30h 25m1 stop Los Angeles
$740Delta
Wed, Jan 20 - Sun, Jan 31
Delta Logo
10:40 am - 1:53 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
20h 13m1 stop Los Angeles
Delta Logo
12:42 pm - 6:50 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 08m2 stops Minneapolis St Paul Los Angeles
$740Delta
Wed, Jan 20 - Sun, Jan 31
Delta Logo
10:40 am - 6:48 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 08m2 stops Los Angeles Atlanta Hartsfield-Jackson
Delta Logo
12:42 pm - 6:50 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
25h 08m2 stops Minneapolis St Paul Los Angeles
$740Delta
Mon, Nov 16 - Mon, Nov 30
Qantas Airways Logo
11:10 am - 4:05 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 55m1 stop Los Angeles
Qantas Airways Logo
9:03 pm - 9:00 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 57m1 stop Los Angeles
$757Qantas Airways
Thu, Feb 18 - Mon, Feb 22
Qantas Airways Logo
2:05 pm - 2:18 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
41h 13m1 stop Dallas/Fort Worth
Qantas Airways Logo
4:59 pm - 9:00 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
23h 01m1 stop Los Angeles
$767Qantas Airways
Tue, Apr 27 - Sat, May 8
Qantas Airways Logo
10:20 am - 4:55 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
21h 35m1 stop Los Angeles
Qantas Airways Logo
8:50 pm - 6:30 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 40m1 stop Los Angeles
$769Qantas Airways
Mon, Apr 26 - Sat, May 8
Qantas Airways Logo
12:00 pm - 7:55 pmSYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 55m1 stop Dallas/Fort Worth
Qantas Airways Logo
8:50 pm - 6:30 amORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
42h 40m1 stop Los Angeles
$769Qantas 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 with more confidence.

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

Round-trip flights from Sydney to Chicago typically range from $1,081 to $1,598. The lowest price found in the past 5 days was $735, 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 $1,299 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?

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’s the cheapest month to fly from Sydney to Chicago?

•October is the cheapest month to fly from Sydney to Chicago at $1,084 round-trip.
•December ($1,690) and September ($1,474) 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

$431
Beat the crowds with an average 51% drop in travelers.
The most popular month to fly with an average 99% increase in travelers.
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 round-trip price

Your Sydney to Chicago flight questions, answered

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

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

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

    • Economy Class
    • Premium Economy Class
    • Business Class
    • First Class

    Prices vary by airline.

  • How long is a flight from Sydney to Chicago?

    A nonstop flight from Sydney to Chicago takes 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 much should I expect to pay for a Sydney to Chicago flight?

    Round-trip flights from Sydney to Chicago range from $1,081 to $1,598, with an average of $1,301 over the past 12 months. Anything below $1,081 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 $1,301 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 lower than usual. Average one-way flight prices are about $617, which is 38% below the typical average for this route.

  • 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 averaging $64:

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

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

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

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • 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 $1,200 round-trip on average, while Saturday is the most expensive at $1,480, a difference of $280.

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

  • 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 53m, compared with 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 Magnificent Mile, Grant Park and Soldier Field. 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 $1,200, about $280 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 $1,084 round-trip in that month - typically $606 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
    • Holiday Inn Chicago - Midway Airport S by IHG
    • 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 rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago