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Cheap flights from Sydney to Chicago from $520

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 6/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Sydney to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Sydney to Chicago.
9:20 am - 2:49 pmSYD-ORD
20h 29m1 stop
3:35 pm - 7:20 amORD-SYD
24h 45m1 stop
$861Air Canada
Find Deal
Thu, Aug 7 - Mon, Aug 25
9:20 am - 10:01 amSYD-ORD
39h 41m2 stops
7:58 pm - 7:20 amORD-SYD
44h 22m2 stops
$954Air Canada
Find Deal
Wed, May 21 - Sun, May 25
9:20 am - 7:59 amSYD-ORD
37h 39m2 stops
3:35 pm - 7:20 amORD-SYD
24h 45m1 stop
$992Air Canada
Find Deal
Wed, Jul 16 - Wed, Jul 30
9:10 am - 3:55 pmSYD-ORD
21h 45m1 stop
7:13 pm - 7:05 amORD-SYD
20h 52m1 stop
$1,017Qantas Airways
Find Deal
Wed, May 21 - Sun, May 25
5:45 pm - 11:59 pmSYD-ORD
21h 14m1 stop
7:13 pm - 7:05 amORD-SYD
20h 52m1 stop
$1,021Qantas Airways
Find Deal
Thu, May 1 - Mon, May 19
9:30 pm - 11:23 amSYD-ORD
28h 53m1 stop
3:17 pm - 7:30 amORD-SYD
25h 13m2 stops
$1,056
Find Deal
Thu, May 1 - Mon, May 19
9:35 pm - 8:04 pmSYD-ORD
37h 29m2 stops
3:40 pm - 8:20 amORD-SYD
24h 40m1 stop
$1,128
Find Deal
Wed, Sep 3 - Fri, Oct 10
9:10 am - 3:56 pmSYD-ORD
21h 46m1 stop
5:02 pm - 7:05 amORD-SYD
23h 03m2 stops
$1,180American Airlines
Find Deal
Fri, Apr 25 - Fri, May 2
5:45 pm - 12:40 amSYD-ORD
21h 55m2 stops
5:02 pm - 7:05 amORD-SYD
23h 03m2 stops
$1,187American Airlines
Find Deal
Fri, Apr 25 - Fri, May 2
9:30 am - 11:41 pmSYD-ORD
29h 11m1 stop
6:30 am - 6:55 amORD-SYD
33h 25m1 stop
$1,332Virgin Australia
Find Deal
Mon, Apr 14 - Wed, Apr 30

Air Canada flights from Sydney to Chicago

Our best Air Canada deals on Sydney to Chicago flight tickets
Air Canada
Aug 7
SYD9:20 amSydney Kingsford Smith
20h 29m
1 stop
ORD2:49 pmChicago O'Hare Intl
Aug 25
ORD3:35 pmChicago O'Hare Intl
24h 45m
1 stop
SYD7:20 amSydney Kingsford Smith
Air Canada
May 21
SYD9:20 amSydney Kingsford Smith
39h 41m
2 stops
ORD10:01 amChicago O'Hare Intl
May 25
ORD7:58 pmChicago O'Hare Intl
44h 22m
2 stops
SYD7:20 amSydney Kingsford Smith
Air Canada
Jul 16
SYD9:20 amSydney Kingsford Smith
37h 39m
2 stops
ORD7:59 amChicago O'Hare Intl
Jul 30
ORD3:35 pmChicago O'Hare Intl
24h 45m
1 stop
SYD7:20 amSydney Kingsford Smith

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
May 21
SYD9:10 amSydney Kingsford Smith
21h 45m
1 stop
ORD3:55 pmChicago O'Hare Intl
May 25
ORD7:13 pmChicago O'Hare Intl
20h 52m
1 stop
SYD7:05 amSydney Kingsford Smith
Qantas Airways
May 1
SYD5:45 pmSydney Kingsford Smith
21h 14m
1 stop
ORD11:59 pmChicago O'Hare Intl
May 19
ORD7:13 pmChicago O'Hare Intl
20h 52m
1 stop
SYD7:05 amSydney Kingsford Smith
Qantas Airways
Apr 15
SYD5:45 pmSydney Kingsford Smith
37h 11m
1 stop
ORD3:56 pmChicago O'Hare Intl
Apr 29
ORD7:20 pmChicago O'Hare Intl
20h 45m
1 stop
SYD7:05 amSydney Kingsford Smith

See travel insights to Chicago from

How to get the cheapest flight ticket from Sydney to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Sydney and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Sydney, with most prices found around $759. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Sydney to Chicago during April average around $866.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Thursday when prices can be found for as low as $1,103. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Sydney to Chicago for around $1,626.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Sydney to Chicago during this time can be as low as $1,141. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $1,365.

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Sydney when booking 21 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,098 when searching 21 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sydney for as low as $849 on momondo.

How have Sydney to Chicago flight prices changed over time?

As of March 2025, prices for Sydney to Chicago flights are approximately 49% cheaper when compared to flights at the same time last year.

When to book flights from Sydney to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sydney to Chicago (SYD to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago

Best Price Found

$520

Fastest flight time

20h 05m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Sydney in the past 72 hours is $520. The best round-trip flight deal from Sydney to Chicago found on momondo in the last 72 hours is $861.
The fastest flight from Sydney to Chicago takes 20h 05m
There are no direct flights from Sydney to Chicago. Popular non-direct routes for this connection are Sydney Kingsford Smith Airport - Chicago Midway Airport and Sydney Kingsford Smith Airport - Chicago O'Hare Intl Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

  • How far is Sydney Kingsford Smith to Chicago by plane?

    A flight from Sydney Kingsford Smith to Chicago will travel around 9237.5 mi. In terms of flight time, this usually takes a little over 20h 09m.

  • When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago?

    Prices for flights from Sydney Kingsford Smith Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Sydney Kingsford Smith Airport to Chicago?

  • How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sydney Kingsford Smith Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Sydney to Chicago?


Best airlines flying from Sydney to Chicago

Compare and see reviews for airlines that fly from Sydney to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Qantas AirwaysPriceFrom $631Free CancellationRating
7.5
811 reviews
Search Qantas Airways flights
American AirlinesPriceFrom $884Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Crown Point
Munster
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Sydney to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sydney to Chicago for you.

Can I find flights from Sydney to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Sydney with this policy.

How can momondo help me find flights from Sydney to Chicago?

Once all potential Sydney to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Sydney to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Sydney to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago