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Find cheap flights to Chicago, Illinois in 2026/2027 from $1,268 This is the cheapest return flight found to Chicago, Illinois from Australia on FlightsFinder on September 18th 2026 at 06:47. This offer may no longer be available. Click the offer to check live prices & dates of travel.
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Our Flight Finder compares the cheapest flights to Chicago, Illinois from the most established flight comparison sites.
Fly to Chicago, Illinois and visit sites like Willis Tower, Navy Pier, Millennium Park & Cloud Gate.
1. Enter your search requirements for Chicago, Illinois
2. Compare the best Chicago, Illinois deals from top comparison engines
3. Book your Chicago, Illinois flight at the cheapest price
These economy flights were found on FlightsFinder from Australia to Chicago, Illinois in the last few days. Prices subject to availability.
These economy flights were found on FlightsFinder from Australia to Chicago, Illinois in the last few days. Prices subject to availability.
According to our data, October is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from $1,268 return.
According to our data, September is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than $1,510.
Chicago, Illinois, fondly known as the "Windy City," is a vibrant metropolis that seamlessly blends tradition with innovation. From its iconic architecture showcasing the birthplace of the skyscraper to its rich cultural scene encompassing world-class museums, theaters, and music venues, Chicago offers a dynamic urban experience like no other. The city's diverse neighborhoods each have their own distinct character, from the historic charm of the Loop to the trendy vibes of Wicker Park. Renowned for its deep-dish pizza, passionate sports fans, and stunning waterfront views along Lake Michigan, Chicago invites visitors to explore its unique blend of history, culture, and modernity.
A good price for a flight to Chicago is $1141 - $1395.
The popular airports near Chicago, Illinois are O'Hare International Airport (ORD), Midway International Airport (MDW), and Chicago Rockford International Airport (RFD).
The flight to Chicago, Illinois (CHI) is roughly 21 hours 1 minute and 9,235 miles (14,862 kilometres) from Sydney, Australia - Kingsford Smith Airport (SYD).
The best way is to compare flights to Chicago, Illinois from leading comparison sites using our search engine dashboard.
We have currently found no direct flights to Chicago, Illinois.
Here is the average weather forecast in Chicago, Illinois by month:
• Jan: -0°C
• Feb: 2°C
• Mar: 8°C
• Apr: 15°C
• May: 21°C
• Jun: 27°C
• Jul: 29°C
• Aug: 28°C
• Sep: 24°C
• Oct: 17°C
• Nov: 9°C
• Dec: 2°C
The main airport in Chicago, Illinois, O'Hare International Airport, is approximately 17 miles from the city center.
Typically, flights are cheapest to Chicago, Illinois 2 months before departure.
Studies show flights to Chicago, Illinois are typically cheaper on Tuesdays and Wednesdays.
19 °C
Fri, 18 Sep 2026
Average Temperature
-0°C
Jan
2°C
Feb
8°C
Mar
15°C
Apr
21°C
May
27°C
Jun
29°C
Jul
28°C
Aug
24°C
Sep
17°C
Oct
9°C
Nov
2°C
Dec
Famously referred to the world over as the windy city, this metropolis lies adjacent to lake Michigan and is a vibrant and popular place.
Originally named the windy city after a commentary once made about it, the actual origin of the term is largely unknown and most believe it acquired its name because of the severe gales which swoop in from the surrounding lake.
Also sometimes refferred to as the 'second city' this land is one of the most populated in the whole of the United States of America. This is the reason it has acquired that name, as it was widely known as the second most populous area after New York.
Another explanation is that it was named the second city after it was rebuilt after the great fire of Chicago destroyed the entire location forcing the people to rebuild the entire area. This is conjectural however and the majority of people prefer the explanation given above.
The most popular tourist attraction in the city is Sears tower.
The amazing city of Chicago has practically something for every type of person – Whether you are into designer shopping, museums, cheap and cheerful unique neighbourhoods, art galleries or historical places of interest, Chicago will not disappoint.
Right adjacent to the lakefront, stretching from Oak Street Beach to the Gold Coast , the city is brimming with activities for one to do. Moreover there are numerous amusement parks, live concerts and riverboat casinos to select from.
It is near impossible to typecaste the people of this city. Whilst before it was infamous as a gangsters haven today it is home to first class theatres, amazing architecture and it is widely known for their abundance of sports enthusiasts.
Chicago has changed quite drastically over the last 50 or so years. Known nowadays as simply one of the finest cities of America, 3 million residents are know settled in what is now mostly known for the art and culture prevalent in the city.
Not fit to be known as the second city anymore, it is a popular place to hold opening events of major cultural occasions.
So what are you waiting for? find your cheap flights to Chicago now!
Happy Searching!
Cheap Flights Finder - Chicago Flights
Sydney, Australia - Kingsford Smith Airport (SYD) to Chicago, Illinois (CHI)
Distance:
9,235 miles (14,862 kilometres)
Average flight time (direct 21 hours 1 minute)
Brisbane, Australia - Brisbane International Airport (BNE) to Chicago, Illinois (CHI)
Distance:
8,903 miles (14,329 kilometres)
Average flight time (direct 20 hours 17 minutes)
Melbourne, Australia - All Airports (MEL) to Chicago, Illinois (CHI)
Distance:
9,666 miles (15,556 kilometres)
Average flight time (direct 21 hours 58 minutes)
Perth, Australia - Perth International Airport (PER) to Chicago, Illinois (CHI)
Distance:
10,955 miles (17,630 kilometres)
Average flight time (direct 24 hours 50 minutes)
Cairns, Australia - Cairns International Airport (CNS) to Chicago, Illinois (CHI)
Distance:
8,845 miles (14,234 kilometres)
Average flight time (direct 20 hours 9 minutes)
Adelaide, Australia - Adelaide International Airport (ADL) to Chicago, Illinois (CHI)
Distance:
9,909 miles (15,948 kilometres)
Average flight time (direct 22 hours 31 minutes)
Darwin, Australia - Darwin International Airport (DRW) to Chicago, Illinois (CHI)
Distance:
9,342 miles (15,035 kilometres)
Average flight time (direct 21 hours 15 minutes)
Gold Coast, Australia - Coolangatta Airport (OOL) to Chicago, Illinois (CHI)
Distance:
8,913 miles (14,344 kilometres)
Average flight time (direct 20 hours 18 minutes)
Townsville, Australia - Townsville International Airport (TSV) to Chicago, Illinois (CHI)
Distance:
8,898 miles (14,320 kilometres)
Average flight time (direct 20 hours 16 minutes)
Mount Isa, Australia - Mount Isa Airport (ISA) to Chicago, Illinois (CHI)
Distance:
9,326 miles (15,009 kilometres)
Average flight time (direct 21 hours 13 minutes)
Kununurra, Australia - Kununurra Airport (KNX) to Chicago, Illinois (CHI)
Distance:
9,612 miles (15,470 kilometres)
Average flight time (direct 21 hours 51 minutes)
Newcastle, Australia - Williamtown Metropolitan Area Airport (NTL) to Chicago, Illinois (CHI)
Distance:
9,163 miles (14,747 kilometres)
Average flight time (direct 20 hours 51 minutes)
Mackay, Australia - Mackay Airport (MKY) to Chicago, Illinois (CHI)
Distance:
8,857 miles (14,254 kilometres)
Average flight time (direct 20 hours 10 minutes)
Hobart, Australia - Hobart International Airport (HBA) to Chicago, Illinois (CHI)
Distance:
9,661 miles (15,549 kilometres)
Average flight time (direct 21 hours 58 minutes)
Launceston, Australia - Launceston Airport (LST) to Chicago, Illinois (CHI)
Distance:
9,647 miles (15,525 kilometres)
Average flight time (direct 21 hours 56 minutes)
Cloncurry, Australia - Cloncurry Airport (CNJ) to Chicago, Illinois (CHI)
Distance:
9,276 miles (14,928 kilometres)
Average flight time (direct 21 hours 6 minutes)
Paraburdoo, Australia - Paraburdoo Airport (PBO) to Chicago, Illinois (CHI)
Distance:
10,471 miles (16,852 kilometres)
Average flight time (direct 23 hours 46 minutes)
Karratha, Australia - Karratha Airport (KTA) to Chicago, Illinois (CHI)
Distance:
10,383 miles (16,710 kilometres)
Average flight time (direct 23 hours 34 minutes)
Kalgoorlie-Boulder, Australia - Kalgoorlie-Boulder Airport (KGI) to Chicago, Illinois (CHI)
Distance:
10,642 miles (17,126 kilometres)
Average flight time (direct 24 hours 8 minutes)
Learmonth, Australia - Learmonth Airport (LEA) to Chicago, Illinois (CHI)
Distance:
10,573 miles (17,015 kilometres)
Average flight time (direct 23 hours 59 minutes)
Port Macquarie, Australia - Port Macquarie Airport (PQQ) to Chicago, Illinois (CHI)
Distance:
9,064 miles (14,588 kilometres)
Average flight time (direct 20 hours 38 minutes)
Port Hedland, Australia - Port Hedland International Airport (PHE) to Chicago, Illinois (CHI)
Distance:
10,289 miles (16,559 kilometres)
Average flight time (direct 23 hours 21 minutes)
Canberra, Australia - Canberra Airport (CBR) to Chicago, Illinois (CHI)
Distance:
9,378 miles (15,092 kilometres)
Average flight time (direct 21 hours 20 minutes)
From Sydney (SYD), Australia to Chicago, United States (ORD): $1,268
Depart: 20 Oct 2026 · Return: 10 Nov 2026 Price found 18 Sep 2026, 06:47
From Melbourne (MEL), Australia to Chicago, United States (ORD): $1,347
Depart: 19 Oct 2026 · Return: 07 Nov 2026 Price found 10 Sep 2026, 22:56
From Brisbane (BNE), Australia to Chicago, United States (ORD): $1,355
Depart: 28 Oct 2026 · Return: 04 Nov 2026 Price found 13 Sep 2026, 19:17
From Adelaide (ADL), Australia to Chicago, United States (ORD): $1,491
Depart: 12 Oct 2026 · Return: 28 Oct 2026 Price found 12 Sep 2026, 23:35
From Perth (PER), Australia to Chicago, United States (ORD): $1,645
Depart: 07 Nov 2026 · Return: 22 Nov 2026 Price found 09 Sep 2026, 14:34
From Gold Coast (OOL), Australia to Chicago, United States (ORD): $1,658
Depart: 08 Oct 2026 · Return: 17 Oct 2026 Price found 12 Sep 2026, 13:45
From Cairns (CNS), Australia to Chicago, United States (ORD): $1,747
Depart: 25 Oct 2026 · Return: 01 Nov 2026 Price found 10 Sep 2026, 12:27
From Mackay (MKY), Australia to Chicago, United States (ORD): $1,749
Depart: 11 Oct 2026 · Return: 17 Oct 2026 Price found 10 Sep 2026, 15:06
From Newcastle (NTL), Australia to Chicago, United States (ORD): $1,757
Depart: 29 Oct 2026 · Return: 05 Nov 2026 Price found 14 Sep 2026, 12:03
From Launceston (LST), Australia to Chicago, United States (ORD): $1,782
Depart: 13 Oct 2026 · Return: 19 Oct 2026 Price found 12 Sep 2026, 13:41
From Hobart (HBA), Australia to Chicago, United States (ORD): $1,837
Depart: 01 Feb 2027 · Return: 05 Feb 2027 Price found 09 Sep 2026, 05:14
From Townsville (TSV), Australia to Chicago, United States (ORD): $1,910
Depart: 02 Oct 2026 · Return: 16 Oct 2026 Price found 14 Sep 2026, 22:05
From Canberra (CBR), Australia to Chicago, United States (ORD): $2,036
Depart: 07 Oct 2026 · Return: 13 Oct 2026 Price found 09 Sep 2026, 14:35
From Darwin (DRW), Australia to Chicago, United States (ORD): $2,161
Depart: 23 Oct 2026 · Return: 30 Oct 2026 Price found 11 Sep 2026, 14:26
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