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Cheap flights from Sydney to Chicago from $494

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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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.
 Logo
1:15 pm - 6:42 amSYD-ORD
32h 27m3 stops
 Logo
2:31 pm - 12:15 pmORD-SYD
30h 44m2 stops
$1,073
Find Deal
Thu, Jun 5 - Thu, Jun 12
 Logo
1:15 pm - 6:42 amSYD-ORD
32h 27m3 stops
 Logo
11:45 am - 12:15 pmORD-SYD
33h 30m3 stops
$1,105
Find Deal
Thu, Jun 5 - Thu, Jun 12
ANA Logo
11:50 am - 4:51 amSYD-ORD
32h 01m2 stops
ANA Logo
5:45 pm - 7:15 pmORD-SYD
34h 30m1 stop
$1,135ANA
Find Deal
Tue, Jun 24 - Tue, Jul 29
ANA Logo
11:50 am - 8:25 pmSYD-ORD
47h 35m2 stops
ANA Logo
5:45 pm - 9:25 amORD-SYD
24h 40m1 stop
$1,248ANA
Find Deal
Mon, Jun 16 - Mon, Jul 14
United Airlines Logo
10:20 am - 6:55 pmSYD-ORD
23h 35m2 stops
United Airlines Logo
6:25 pm - 7:00 amORD-SYD
21h 35m1 stop
$1,339United Airlines
Find Deal
Mon, Aug 4 - Mon, Aug 25
United Airlines Logo
10:20 am - 5:39 amSYD-ORD
34h 19m1 stop
United Airlines Logo
2:26 pm - 7:00 amORD-SYD
25h 34m2 stops
$1,385United Airlines
Find Deal
Fri, Jun 27 - Sun, Jul 13
Qantas Airways Logo
9:10 am - 11:35 pmSYD-ORD
29h 25m1 stop
Qantas Airways Logo
8:50 am - 7:05 amORD-SYD
31h 15m1 stop
$1,418Qantas Airways
Find Deal
Thu, Jun 26 - Tue, Jul 15
Qantas Airways Logo
9:10 am - 11:35 pmSYD-ORD
29h 25m1 stop
Qantas Airways Logo
6:45 pm - 7:05 amORD-SYD
21h 20m1 stop
$1,577Qantas Airways
Find Deal
Thu, Jun 26 - Mon, Jul 14
American Airlines Logo
9:30 pm - 5:13 amSYD-ORD
22h 43m2 stops
American Airlines Logo
1:23 pm - 7:05 amORD-SYD
26h 42m2 stops
$1,642American Airlines
Find Deal
Sun, Jun 29 - Tue, Jul 15
American Airlines Logo
9:10 am - 5:12 pmSYD-ORD
23h 02m2 stops
American Airlines Logo
10:37 pm - 7:05 amORD-SYD
41h 28m1 stop
$1,708American Airlines
Find Deal
Tue, May 6 - Sat, May 10

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
Jun 24
SYD11:50 amSydney Kingsford Smith
32h 01m
2 stops
ORD4:51 amChicago O'Hare Intl
Jul 29
ORD5:45 pmChicago O'Hare Intl
34h 30m
1 stop
SYD7:15 pmSydney Kingsford Smith
ANA
Jun 16
SYD11:50 amSydney Kingsford Smith
47h 35m
2 stops
ORD8:25 pmChicago O'Hare Intl
Jul 14
ORD5:45 pmChicago O'Hare Intl
24h 40m
1 stop
SYD9:25 amSydney Kingsford Smith
ANA
Aug 10
SYD11:50 amSydney Kingsford Smith
32h 01m
2 stops
ORD4:51 amChicago O'Hare Intl
Aug 24
ORD5:45 pmChicago O'Hare Intl
24h 40m
1 stop
SYD9:25 amSydney Kingsford Smith

Japan Airlines flights from Sydney to Chicago

Our best Japan Airlines deals on Sydney to Chicago flight tickets
Japan Airlines
Jun 5
SYD8:55 amSydney Kingsford Smith
49h 34m
2 stops
ORD7:29 pmChicago O'Hare Intl
Jun 11
ORD1:30 amChicago O'Hare Intl
37h 50m
1 stop
SYD6:20 amSydney Kingsford Smith
Japan Airlines
Jun 9
SYD8:55 amSydney Kingsford Smith
49h 34m
2 stops
ORD7:29 pmChicago O'Hare Intl
Jun 19
ORD1:30 amChicago O'Hare Intl
37h 50m
1 stop
SYD6:20 amSydney Kingsford Smith
Japan Airlines
May 29
SYD8:55 amSydney Kingsford Smith
28h 37m
2 stops
ORD10:32 pmChicago O'Hare Intl
Jun 15
ORD1:30 amChicago O'Hare Intl
37h 50m
1 stop
SYD6:20 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 cheapest month to fly to Chicago?

The month of March is, on average, the cheapest month to fly to Chicago from Sydney, with most prices found around $748. If you’re not able to fly to Chicago in March, then February is your next best option. Flight prices from Sydney to Chicago during February average around $759.

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 20 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,076 when searching 20 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 $857 on momondo.

How have Sydney to Chicago flight prices changed over time?

As of April 2025, prices for Sydney to Chicago flights are approximately 53% 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

$494

Fastest flight time

19h 32m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Sydney in the past 72 hours is $494. The best round-trip flight deal from Sydney to Chicago found on momondo in the last 72 hours is $1,073.
The fastest flight from Sydney to Chicago takes 19h 32m
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 19h 32m.

  • 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
826 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
Benton Harbor
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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