Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Sydney to Chicago from $420

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 3/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Sydney to Chicago

Cheap round-trip flights

These are some of the best round-trip flight deals from Sydney to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Sydney to Chicago.

Cheap last minute flights

Planning a quick getaway from Sydney to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Sydney to Chicago

Find recent round-trip train or bus tickets from Sydney to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
11:15 am - 3:59 pmSYD-ORD
21h 44m1 stop
5:40 pm - 9:00 amORD-SYD
22h 20m1 stop
$703Qantas Airways
Find Deal
Tue, Feb 4 - Tue, Feb 11
11:15 am - 3:59 pmSYD-ORD
21h 44m1 stop
9:45 am - 7:25 amORD-SYD
28h 40m1 stop
$718Qantas Airways
Find Deal
Thu, Jan 23 - Wed, Feb 5
5:25 pm - 11:57 pmSYD-ORD
23h 32m1 stop
8:00 pm - 8:15 pmORD-SYD
32h 15m2 stops
Mon, Mar 3 - Mon, Mar 10
2:00 pm - 11:13 pmSYD-ORD
26h 13m2 stops
11:10 am - 1:00 pmORD-SYD
32h 50m2 stops
Thu, Jan 23 - Thu, Jan 30
8:55 pm - 8:40 amSYD-ORD
26h 45m1 stop
7:15 am - 9:25 amORD-SYD
59h 10m2 stops
$1,254ANA
Find Deal
Fri, May 16 - Fri, May 23
10:20 am - 6:54 pmSYD-ORD
23h 34m2 stops
12:45 pm - 7:00 amORD-SYD
27h 15m2 stops
$1,401United Airlines
Find Deal
Fri, May 16 - Fri, May 23
11:50 am - 5:03 amSYD-ORD
32h 13m2 stops
5:45 pm - 7:15 pmORD-SYD
34h 30m1 stop
$1,440ANA
Find Deal
Fri, May 23 - Fri, Jun 6
12:10 pm - 6:55 pmSYD-ORD
23h 45m2 stops
2:35 pm - 9:05 amORD-SYD
25h 30m2 stops
$1,497United Airlines
Find Deal
Tue, Jan 14 - Tue, Feb 25
11:15 am - 1:58 pmSYD-ORD
19h 43m1 stop
3:22 pm - 9:00 amORD-SYD
24h 38m2 stops
$2,446American Airlines
Find Deal
Wed, Jan 1 - Wed, Jan 29
11:15 am - 1:58 pmSYD-ORD
19h 43m1 stop
2:14 pm - 9:00 amORD-SYD
25h 46m1 stop
$2,497American Airlines
Find Deal
Wed, Jan 1 - Thu, Jan 23
5:25 pm - 5:53 amSYD-ORD
28h 28m2 stops
Mon, Mar 10
2:00 pm - 10:09 pmSYD-MDW
25h 09m2 stops
Tue, Feb 18
11:15 am - 5:10 pmSYD-ORD
22h 55m1 stop
$447Qantas Airways
Find Deal
Tue, Feb 18
5:25 pm - 11:57 pmSYD-ORD
23h 32m1 stop
$449Qantas Airways
Find Deal
Sun, Feb 16
3:15 pm - 1:00 pmSYD-ORD
38h 45m1 stop
$772Cathay Pacific
Find Deal
Wed, Feb 26
12:00 pm - 1:00 pmSYD-ORD
42h 00m2 stops
$803Cathay Pacific
Find Deal
Wed, Feb 26
10:30 am - 11:41 pmSYD-ORD
29h 11m1 stop
$828United Airlines
Find Deal
Thu, Apr 3
10:30 am - 7:15 pmSYD-ORD
24h 45m2 stops
$831United Airlines
Find Deal
Wed, Apr 2
11:05 am - 10:20 pmSYD-MDW
28h 15m2 stops
$833Delta
Find Deal
Mon, Feb 17
11:05 am - 5:43 pmSYD-MDW
23h 38m2 stops
$835Delta
Find Deal
Wed, Feb 26

Qantas Airways flights from Sydney to Chicago

Our best Qantas Airways deals on Sydney to Chicago flight tickets
Qantas Airways
Feb 4
SYD11:15 amSydney Kingsford Smith
21h 44m
1 stop
ORD3:59 pmChicago O'Hare Intl
Feb 11
ORD5:40 pmChicago O'Hare Intl
22h 20m
1 stop
SYD9:00 amSydney Kingsford Smith
Qantas Airways
Jan 23
SYD11:15 amSydney Kingsford Smith
21h 44m
1 stop
ORD3:59 pmChicago O'Hare Intl
Feb 5
ORD9:45 amChicago O'Hare Intl
28h 40m
1 stop
SYD7:25 amSydney Kingsford Smith
Qantas Airways
May 24
SYD5:35 pmSydney Kingsford Smith
37h 10m
1 stop
ORD3:45 pmChicago O'Hare Intl
Jun 6
ORD6:25 pmChicago O'Hare Intl
21h 10m
1 stop
SYD6:35 amSydney Kingsford Smith

ANA flights from Sydney to Chicago

Our best ANA deals on Sydney to Chicago flight tickets
ANA
May 16
SYD8:55 pmSydney Kingsford Smith
26h 45m
1 stop
ORD8:40 amChicago O'Hare Intl
May 23
ORD7:15 amChicago O'Hare Intl
59h 10m
2 stops
SYD9:25 amSydney Kingsford Smith
ANA
May 23
SYD11:50 amSydney Kingsford Smith
32h 13m
2 stops
ORD5:03 amChicago O'Hare Intl
Jun 6
ORD5:45 pmChicago O'Hare Intl
34h 30m
1 stop
SYD7:15 pmSydney 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 $1,068. 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 $1,084.

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?

The best time to book a flight to Chicago from Sydney is 55 days out, which is when prices tend to be around $1,245. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $712.

Can stopping save me money on Sydney to Chicago flights?

You could potentially save up to 6% on your flight if you consider stops on a Sydney to Chicago flight.

How have Sydney to Chicago flight prices changed over time?

As of December 2024, prices for Sydney to Chicago flights are approximately 1% more expensive 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

$420

Fastest flight time

19h 43m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Sydney in the past 72 hours is $420. The best round-trip flight deal from Sydney to Chicago found on momondo in the last 72 hours is $703.
The fastest flight from Sydney to Chicago takes 19h 43m
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 43m.

  • 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
American AirlinesPriceFrom $884Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $964Free CancellationRating
7.4
9,059 reviews
Search United Airlines flights

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.


An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Mon 12/23
Mon 12/30
Email me momondo's favorite deals

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