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Look for other cheap flights to Chicago

$869 Cheap flights to Chicago

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight to Chicago departing on 21/7. 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 Australia to Chicago

Cheap return flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
13:15 - 05:35
SYD
-
ORD
31h 20m
2 stops
Multiple Airlines Logo
15:00 - 11:50
ORD
-
SYD
29h 50m
2 stops
$1,303Multiple Airlines
Sat, 25 Apr - Sat, 2 May
Multiple Airlines Logo
13:25 - 23:27
MEL
-
ORD
25h 02m
2 stops
Multiple Airlines Logo
07:30 - 12:05
ORD
-
MEL
37h 35m
2 stops
$1,330Multiple Airlines
Wed, 29 Apr - Wed, 6 May
Multiple Airlines Logo
13:30 - 23:27
MEL
-
ORD
24h 57m
2 stops
Multiple Airlines Logo
14:39 - 12:25
ORD
-
MEL
30h 46m
2 stops
$1,337Multiple Airlines
Mon, 27 Apr - Mon, 4 May
Air Canada Logo
10:00 - 19:25
BNE
-
ORD
24h 25m
2 stops
Air Canada Logo
09:55 - 07:05
ORD
-
BNE
30h 10m
2 stops
$1,353Air Canada
Tue, 28 Apr - Tue, 5 May
Air Canada Logo
10:00 - 20:15
BNE
-
ORD
25h 15m
1 stop
Air Canada Logo
15:40 - 07:05
ORD
-
BNE
24h 25m
1 stop
$1,417Air Canada
Tue, 21 Apr - Sat, 2 May
Air New Zealand Logo
11:55 - 23:16
SYD
-
ORD
26h 21m
2 stops
Air New Zealand Logo
15:47 - 08:45
ORD
-
SYD
25h 58m
2 stops
$1,449Air New Zealand
Tue, 2 Jun - Fri, 19 Jun
Air New Zealand Logo
11:55 - 23:16
SYD
-
ORD
26h 21m
2 stops
Air New Zealand Logo
15:47 - 08:45
ORD
-
SYD
25h 58m
2 stops
$1,459Air New Zealand
Tue, 2 Jun - Fri, 19 Jun
Qantas Airways Logo
11:50 - 23:59
ADL
-
ORD
26h 39m
2 stops
Qantas Airways Logo
15:07 - 09:25
ORD
-
ADL
27h 48m
2 stops
$1,916Qantas Airways
Sat, 18 Apr - Fri, 24 Apr
American Airlines Logo
07:00 - 20:21
OOL
-
ORD
28h 21m
2 stops
American Airlines Logo
06:00 - 10:40
ORD
-
OOL
37h 40m
2 stops
$2,374American Airlines
Wed, 3 Jun - Sat, 6 Jun
American Airlines Logo
07:00 - 18:11
OOL
-
ORD
26h 11m
2 stops
American Airlines Logo
06:00 - 15:05
ORD
-
OOL
42h 05m
2 stops
$2,375American Airlines
Wed, 3 Jun - Sat, 6 Jun

momondo Fare Finder

 
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, momondo users made a total of 78,305 searches and data was last updated on 16 March 2026.
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 - ORD

SYDORD

Sydney Kingsford Smith

Sat 25/4

13:15-05:35

2 stops31h 20m

Chicago O'Hare Intl

Sat 2/5

15:00-11:50

2 stops29h 50m

$1,303

MelbourneChicago

MEL - ORD

MELORD

Melbourne

Wed 29/4

13:25-23:27

2 stops25h 02m

Chicago O'Hare Intl

Wed 6/5

07:30-12:05

2 stops37h 35m

$1,330

MelbourneChicago

MEL - ORD

MELORD

Melbourne

Mon 27/4

13:30-23:27

2 stops24h 57m

Chicago O'Hare Intl

Mon 4/5

14:39-12:25

2 stops30h 46m

$1,337

BrisbaneChicago

BNE - ORD

BNEORD

Brisbane

Tue 28/4

10:00-19:25

2 stops24h 25m

Chicago O'Hare Intl

Tue 5/5

09:55-07:05

2 stops30h 10m

$1,353
Fastest return journey

BrisbaneChicago

BNE - ORD

BNEORD

Brisbane

Tue 21/4

10:00-20:15

1 stop25h 15m

Chicago O'Hare Intl

Sat 2/5

15:40-07:05

1 stop24h 25m

$1,417

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/6

11:55-23:16

2 stops26h 21m

Chicago O'Hare Intl

Fri 19/6

15:47-08:45

2 stops25h 58m

$1,449

SydneyChicago

SYD - ORD

SYDORD

Sydney Kingsford Smith

Tue 2/6

11:55-23:16

2 stops26h 21m

Chicago O'Hare Intl

Fri 19/6

15:47-08:45

2 stops25h 58m

$1,459

AdelaideChicago

ADL - ORD

ADLORD

Adelaide

Sat 18/4

11:50-23:59

2 stops26h 39m

Chicago O'Hare Intl

Fri 24/4

15:07-09:25

2 stops27h 48m

$1,916

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Wed 3/6

07:00-20:21

2 stops28h 21m

Chicago O'Hare Intl

Sat 6/6

06:00-10:40

2 stops37h 40m

$2,374

CoolangattaChicago

OOL - ORD

OOLORD

Coolangatta Gold Coast

Wed 3/6

07:00-18:11

2 stops26h 11m

Chicago O'Hare Intl

Sat 6/6

06:00-15:05

2 stops42h 05m

$2,375

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 August, then you should wait until July to fly from Australia, when ticket prices are also cheap, with an average price of $1,572.

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 $1,832 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 $1,200 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 SYDNEYAugust11% cheaperFlying from Sydney to Chicago costs on average just $1,499 in August
MOST EXPENSIVE MONTH TO FLY TO CHICAGO FROM SYDNEYDecember14% more expensiveIt costs about $1,906 for flights to Chicago from Sydney in December
MOST POPULAR MONTH TO FLY TO CHICAGO FROM SYDNEYJuly390% more users visitedMore momondo users searched in flights to Chicago from Sydney in July than any other month

Cheap Chicago flight deals and tips

Summary info about Chicago flight prices, duration and airlines

Best One-Way Price

$869

Best Round-Trip Price

$1,303

Fastest flight time

24h 40m

Popular in

December
The best one-way flight price to Chicago from Australia in the last 72 hours is $869 (Sydney Kingsford Smith to Chicago O'Hare Intl).
Search Deals
The best round-trip flight price to Chicago from Australia in the last 72 hours is $1,303 (Sydney Kingsford Smith to Chicago O'Hare Intl).
Search Deals
The fastest flight to Chicago from Australia takes 24h 40m (Sydney Kingsford Smith to Chicago O'Hare Intl).
Search Deals
December has the highest demand for flights to Chicago, with a 6% 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 Chicago Riverwalk, Millennium Park, and Art Institute of Chicago 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 87 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 $1,666. In the past 72 hours, momondo users found flights from Australia to Chicago for as low as $1,071.

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 Greater Rockford Airport for $136 on average, but that price can change based on your departure airport. To save money, try momondo’s Airport-to-Airport Pricing Tool.

Are there flights to Grand Boulevard?

Yes. To go to Grand Boulevard, book a flight to Chicago O'Hare Intl which is in Chicago and is about 30.1 km away from Grand Boulevard.

What’s the closest airport to River North?

The closest airport to River North is 24.1 km away - Chicago’s Chicago O'Hare Intl 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 10 operators available for flights to Chicago as of March 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

Popular routes according to searches in the past day on momondo
Sydney Kingsford Smith to Chicago Flightsfrom $1,036
Brisbane to Chicago Flightsfrom $1,006
Melbourne to Chicago Flightsfrom $922
Adelaide to Chicago Flightsfrom $1,188
Perth to Chicago Flightsfrom $1,426
Cairns to Chicago Flightsfrom $1,776
Coolangatta Gold Coast to Chicago Flightsfrom $1,484
Townsville to Chicago Flightsfrom $2,133