Cheap flights from Chicago to Sydney from $717 MDW, ORD, RFD → SYD, WSI
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Sydney (Kingsford Smith) Airport (SYD), Western Sydney Airport (WSI)
The cheapest return found recently is $1,296 with American Airlines, 25 Aug 2027 – 3 Sept 2027, found 2 days ago. The cheapest one-way found recently is $717 with Philippine Airlines, 29 Sept 2027, found 3 days ago.
- Cheapest one-way found recently
- $717, Philippine Airlines, found 3 days ago
- Cheapest return found recently
- $1,296, 25 Aug 2027 to 3 Sept 2027
- Usual return price
- $1,265 to $1,296
- Cheapest month to fly
- June 2027, return fares from $1,069 found in the last 7 days
Return
The cheapest return fare on each of 5 departure dates is usually $1,265 to $1,296.
Cheapest return found recently
$1,296
25 Aug 2027 – 3 Sept 2027 · American Airlines
O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD)
Leaves 7:07 p.m. · Return leaves 6:54 a.m. · 41 h 22 min of travel, both ways together
out 1 stop, back 1 stop · via Dallas/Fort Worth International Airport (DFW), Los Angeles International Airport (LAX)
found 2 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$1,296 25 Aug 2027 – 3 Sept 2027found 2 days agoSee prices for these dates
$1,069 15 Jun 2027 – 10 Jul 2027found 7 days agoSee prices for these dates
What have prices looked like?
Over 24 days, 27 Sept to 11 Nov, the cheapest return we saw each day was $1,069 to $1,593.
24 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 5 departure dates from 19 Dec to 26 Aug 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
We hold no other 9-night return fares leaving within 3 days of 25 Aug 2027 to compare.
Every date we hold
16 fares on 5 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 19 Dec – 2 Jan 2027 | $4,690 | Allegiant Air | Chicago Rockford International Airport (RFD) → Sydney (Kingsford Smith) Airport (SYD) | out 2 stops, back 2 stops | found 4 days ago | See prices for these dates |
| 4 Jun 2027 – 20 Jun 2027 | $1,265 | American Airlines | O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD) | out 2 stops, back 1 stop | found 7 days ago | See prices for these dates |
| 15 Jun 2027 – 10 Jul 2027 | $1,069 | Air Canada | O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD) | out 1 stop, back 1 stop | found 7 days ago | See prices for these dates |
| 25 Aug 2027 – 3 Sept 2027 | $1,296 | American Airlines | O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
| 26 Aug 2027 – 2 Sept 2027 | $1,296 | American Airlines | O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD) | out 1 stop, back 1 stop | found 2 days ago | See prices for these dates |
Which month looks cheapest?
June 2027 is the cheapest month — from $1,069.
Airlines on the cheapest dates: American Airlines, Allegiant Air, Air Canada.
One-way
Not enough comparable prices yet for a usual one-way price.
Cheapest one-way found recently
$717
29 Sept 2027 · Philippine Airlines
O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD)
Leaves 11:45 p.m. · 43 h trip
1 stop · via Ninoy Aquino International Airport (MNL) · 17 h connection
found 3 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$717 29 Sept 2027found 3 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 4 days, 26 Sept to 11 Nov, the cheapest one-way we saw each day was $717 to $1,511.
At $717, the cheapest one-way found recently is at the low end of that range.
4 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Not enough comparable prices yet: we hold one-way fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 29 Sept 2027 to compare.
Every date we hold
9 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 29 Sept 2027 | $717 | Philippine Airlines | O'Hare International Airport (ORD) → Sydney (Kingsford Smith) Airport (SYD) | 1 stop | found 3 days ago | Open this trip |
Airlines on the cheapest dates: Philippine Airlines.
Premium cabin fares from Chicago to Sydney
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 25 Aug 2027 – 3 Sept 2027 in another cabin: Premium economy · Business · First
Today's prices for 29 Sept 2027 in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Sydney?
Return
Fares 180 or more days before departure were typically 17% lower than 30 to 59 days before departure.
From the cheapest return each day between 27 Sept and 11 Nov (24 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 30–59 days | $1,492 | $1,492 | +21% | 8 |
| 60–89 days | $2,953 | $2,953 | +139% | 7 |
| 90–179 days | $1,384 | $1,299 | +12% | 13 |
| 180+ days | $1,237 | $1,069 | Cheapest seen | 17 |
One-way
Not enough history yet: we have 4 days of one-way prices, 26 Sept to 11 Nov, and compare booking times once 3 booking ranges have 7 days each.
Live price for these dates
The cheapest return found recently is for 25 Aug 2027 – 3 Sept 2027. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Chicago to Sydney?
The cheapest return found recently is $1,296 with American Airlines, 25 Aug 2027 to 3 Sept 2027, found 2 days ago. The cheapest return we hold, of any age, is $1,069 with Air Canada, 15 Jun 2027 to 10 Jul 2027, found 7 days ago. The cheapest return fare on each of 5 departure dates is usually $1,265 to $1,296.
How much is a one-way flight from Chicago to Sydney?
The cheapest one-way found recently is $717 with Philippine Airlines, 29 Sept 2027, found 3 days ago.
What is the cheapest month to fly from Chicago to Sydney?
June 2027 is the cheapest month for a return, from $1,069, 15 Jun 2027 to 10 Jul 2027, found 7 days ago.
How far ahead should I book a flight from Chicago to Sydney?
In 24 days of prices between 27 Sept and 11 Nov, return fares 180 or more days before departure were typically 17% lower than 30 to 59 days before departure.
How long is the flight from Chicago to Sydney?
The cheapest one-way found recently, with Philippine Airlines on 29 Sept 2027, takes 43 h with 1 stop, including a 17 h connection.
Which airlines have the cheapest flights from Chicago to Sydney?
Between 19 Dec and 26 Aug 2027, American Airlines has the cheapest return on 3 of the 5 departure dates we hold, Allegiant Air on 1 and Air Canada on 1.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work