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$946 Cheap flights to Chicago

1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Australia to Chicago

Cheap return flights

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Multiple Airlines Logo
06:05 - 19:02SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
52h 57m3 stops Nadi Los Angeles Orlando
Multiple Airlines Logo
06:30 - 12:50ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
38h 20m3 stops Denver Intl Los Angeles Nadi
$1,314Multiple Airlines
Thu, 8 Oct - Wed, 21 Oct
Qantas Airways Logo
21:25 - 05:00SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 35m1 stop San Francisco
Qantas Airways Logo
08:23 - 07:05ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 42m1 stop Los Angeles
$1,382Qantas Airways
Sun, 27 Sep - Mon, 28 Sep
Multiple Airlines Logo
09:10 - 00:23SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
30h 13m2 stops Los Angeles Denver Intl
Multiple Airlines Logo
06:00 - 07:05ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 05m2 stops Dallas/Fort Worth Los Angeles
$1,464Multiple Airlines
Tue, 22 Sep - Tue, 29 Sep
American Airlines Logo
10:10 - 12:21SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
42h 11m1 stop Los Angeles
American Airlines Logo
13:46 - 06:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 39m2 stops Dallas/Fort Worth San Francisco
$1,664American Airlines
Thu, 15 Oct - Tue, 20 Oct
American Airlines Logo
10:10 - 12:20SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
42h 10m1 stop Los Angeles
American Airlines Logo
13:46 - 06:25ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
24h 39m2 stops Dallas/Fort Worth San Francisco
$1,664American Airlines
Wed, 14 Oct - Tue, 20 Oct
Air New Zealand Logo
11:50 - 22:00SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
27h 10m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
10:34 - 10:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
31h 01m2 stops Houston George Bush Intcntl Auckland Intl
$1,721Air New Zealand
Wed, 4 Nov - Mon, 9 Nov
Air New Zealand Logo
11:55 - 21:31SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 36m2 stops Auckland Intl Los Angeles
Air New Zealand Logo
15:47 - 18:15ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
34h 28m2 stops Los Angeles Auckland Intl
$1,747Air New Zealand
Wed, 14 Oct - Wed, 28 Oct
Qantas Airways Logo
13:00 - 19:16SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
22h 16m1 stop Dallas/Fort Worth
Qantas Airways Logo
08:29 - 09:00ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
32h 31m1 stop Los Angeles
$1,781Qantas Airways
Wed, 14 Oct - Fri, 30 Oct
Air Canada Logo
10:20 - 18:43SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
24h 23m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
11:05 - 08:20ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 15m3 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl Vancouver Intl
$2,119Air Canada
Wed, 14 Oct - Mon, 19 Oct
Air Canada Logo
11:20 - 20:01SYD  Sydney Kingsford Smith-ORD Chicago O'Hare Intl
25h 41m1 stop Vancouver Intl
Air Canada Logo
10:40 - 09:35ORD  Chicago O'Hare Intl-SYD Sydney Kingsford Smith
29h 55m2 stops Montreal Pierre Elliott Trudeau Intl Vancouver Intl
$2,218Air Canada
Mon, 16 Nov - Tue, 9 Feb

momondo Fare Finder

 
Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 8/10

06:05-19:02

3 stops52h 57m

Chicago O'Hare Intl

Wed 21/10

06:30-12:50

3 stops38h 20m

$1,314

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Sun 27/9

21:25-05:00

1 stop22h 35m

Chicago O'Hare Intl

Mon 28/9

08:23-07:05

1 stop31h 42m

$1,382

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Tue 22/9

09:10-00:23

2 stops30h 13m

Chicago O'Hare Intl

Tue 29/9

06:00-07:05

2 stops34h 05m

$1,464

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Thu 15/10

10:10-12:21

1 stop42h 11m

Chicago O'Hare Intl

Tue 20/10

13:46-06:25

2 stops24h 39m

$1,664

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 14/10

10:10-12:20

1 stop42h 10m

Chicago O'Hare Intl

Tue 20/10

13:46-06:25

2 stops24h 39m

$1,664

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 4/11

11:50-22:00

2 stops27h 10m

Chicago O'Hare Intl

Mon 9/11

10:34-10:35

2 stops31h 01m

$1,721

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 14/10

11:55-21:31

2 stops25h 36m

Chicago O'Hare Intl

Wed 28/10

15:47-18:15

2 stops34h 28m

$1,747

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 14/10

13:00-19:16

1 stop22h 16m

Chicago O'Hare Intl

Fri 30/10

08:29-09:00

1 stop32h 31m

$1,781
Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Wed 14/10

10:20-18:43

2 stops24h 23m

Chicago O'Hare Intl

Mon 19/10

11:05-08:20

3 stops29h 15m

$2,119

SydneyChicago

SYD Sydney Kingsford Smith - ORD Chicago O'Hare Intl

SYDORD

Sydney Kingsford Smith

Mon 16/11

11:20-20:01

1 stop25h 41m

Chicago O'Hare Intl

Tue 9/2

10:40-09:35

2 stops29h 55m

$2,218

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

Chicago flights insights and trends

Explore insights for your Chicago flight to craft the best travel plan

What is the cheapest month to fly to Chicago?

If you don’t want to visit Chicago in October, then you should wait until March to fly from Australia, when ticket prices are also cheap, with an average price of $1,535.

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

You are more likely to see cheaper flights to Chicago from Australia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $1,948 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Australia for as low as $1,219 on momondo.

Cheapest flights to Chicago

Find the cheapest flights to Chicago from your nearest city or airport
Find flights from Sydney to Chicago O'Hare Intl Airport
CHEAPEST MONTH TO FLY TO CHICAGO FROM SYDNEYOctober18% cheaperFlying from Sydney to Chicago costs on average just $1,438 in October
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM SYDNEYMay34% more expensiveIt costs about $2,330 for flights to Chicago from Sydney in May
MOST POPULAR MONTH TO FLY TO CHICAGO FROM SYDNEYDecember382% more users visitedMore momondo users searched in flights to Chicago from Sydney in December than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

$946

Best Round-Trip Price

$1,314

Fastest flight time

28h 50m

Popular in

August
The best one-way flight price to Chicago from Australia in the last 5 days is $946 (Sydney Kingsford Smith to Chicago O'Hare Intl).
Search Deals
The best return flight price to Chicago from Australia in the last 5 days is $1,314 (Sydney Kingsford Smith to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from Australia takes 28h 50m (Brisbane to Chicago O'Hare Intl).
Search Deals
August has the highest demand for flights to Chicago, with a 11% price increase on average.
Search Deals

Frequently asked questions about flying to Chicago

When is it best to fly to Chicago to go sightseeing?

Sights like Millennium Park, Art Institute of Chicago, and Chicago Riverwalk are most enjoyable in months with moderate weather conditions like May or June. Plan your flight to Chicago for those months.

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

We recommend purchasing flights from Australia to Chicago 61 days ahead of your departure date because this is when momondo users tend to see the best flight rates. On average, our users have found flights to Chicago for $1,737.

Is there an alternative airport near Chicago?

Finding an alternative and possibly cheaper destination airport near Chicago is possible. If you are planning a flight to Chicago, consider booking flights to Chicago Midway Airport (14 km from Chicago city centre) or Chicago Greater Rockford Airport (126 km from Chicago city centre).

Is there a cheaper alternative to flying into Chicago?

You can find deals at Chicago Midway Airport for $350 on average, but that price can change based on your departure airport. To save money, try momondo’s Airport-to-Airport Pricing Tool.

What is the absolute cheapest flight to Chicago?

The best price found on momondo to Chicago was $311/pp from Boston, which is 11% cheaper than the average flight price to Chicago. To find the cheapest price to Chicago from your area, use momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Near West Side?

Yes. To go to Near West Side, book a flight to Chicago Midway which is in Chicago and is about 12.5 km away from Near West Side.

What’s the closest airport to River North?

The closest airport to River North is 15.1 km away - Chicago’s Chicago Midway airport.

When did momondo last update prices for flights to Chicago?

Prices for flights to Chicago refresh daily.

How many operators does momondo search for flights to Chicago?

There are 8 operators available for flights to Chicago as of August 2026.

How old do you have to be to fly to Chicago?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and stopovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel to Chicago.

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

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s licence, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

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

It is quick and easy to find flights to Chicago on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for flights to Chicago to just show those with flexible booking policies.

How can momondo help me find flights to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight to Chicago.

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

Yes. momondo can track flight prices for Chicago and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Chicago

Popular Flights to Chicago

Sydney Kingsford Smith to Chicago Flightsfrom $992
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Adelaide to Chicago Flightsfrom $1,506
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