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Cheap flights from Sydney to Chicago from $1,149

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 16/11. 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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Cheap return flights

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Multiple Airlines Logo
11:20 - 12:30SYD-MDW
41h 10m2 stops
Multiple Airlines Logo
06:30 - 09:00MDW-SYD
33h 30m2 stops
$1,729Multiple Airlines
Find Deal
Sat, 1 Nov - Sun, 16 Nov
Delta Logo
10:40 - 16:24SYD-MDW
22h 44m2 stops
Delta Logo
09:30 - 08:30MDW-SYD
30h 00m2 stops
$2,145Delta
Find Deal
Fri, 26 Dec - Mon, 2 Feb
Delta Logo
10:40 - 22:22SYD-MDW
28h 42m2 stops
Delta Logo
13:05 - 06:50MDW-SYD
24h 45m2 stops
$2,219Delta
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Wed, 24 Dec - Tue, 3 Feb
Delta Logo
10:40 - 18:18SYD-MDW
24h 38m2 stops
Delta Logo
13:47 - 08:30MDW-SYD
25h 43m2 stops
$2,368Delta
Find Deal
Wed, 12 Nov - Wed, 19 Nov
Delta Logo
10:40 - 22:22SYD-MDW
28h 42m2 stops
Delta Logo
13:00 - 06:50MDW-SYD
24h 50m2 stops
$2,445Delta
Find Deal
Wed, 24 Dec - Thu, 22 Jan
Delta Logo
10:40 - 16:38SYD-MDW
22h 58m2 stops
Delta Logo
09:41 - 08:30MDW-SYD
29h 49m2 stops
$2,456Delta
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Sun, 16 Nov - Sun, 30 Nov
Delta Logo
10:40 - 17:43SYD-MDW
24h 03m2 stops
Delta Logo
10:47 - 08:30MDW-SYD
28h 43m2 stops
$2,524Delta
Find Deal
Mon, 3 Nov - Mon, 17 Nov
Delta Logo
09:40 - 17:43SYD-MDW
24h 03m2 stops
Delta Logo
13:47 - 08:30MDW-SYD
25h 43m2 stops
$2,531Delta
Find Deal
Mon, 27 Oct - Sun, 9 Nov
Delta Logo
09:40 - 17:55SYD-MDW
24h 15m2 stops
Delta Logo
09:34 - 08:30MDW-SYD
29h 56m2 stops
$2,593Delta
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Sat, 1 Nov - Wed, 19 Nov
Multiple Airlines Logo
13:05 - 23:20SYD-MDW
26h 15m1 stop
Multiple Airlines Logo
12:30 - 07:25MDW-SYD
49h 55m2 stops
$2,596Multiple Airlines
Find Deal
Mon, 27 Oct - Sun, 9 Nov

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
26 Dec
SYD10:40Sydney Kingsford Smith
22h 44m
2 stops
MDW16:24Chicago Midway
2 Feb
MDW09:30Chicago Midway
30h 00m
2 stops
SYD08:30Sydney Kingsford Smith
$2,145
Find similar
Delta
24 Dec
SYD10:40Sydney Kingsford Smith
28h 42m
2 stops
MDW22:22Chicago Midway
3 Feb
MDW13:05Chicago Midway
24h 45m
2 stops
SYD06:50Sydney Kingsford Smith
$2,219
Find similar
Delta
12 Nov
SYD10:40Sydney Kingsford Smith
24h 38m
2 stops
MDW18:18Chicago Midway
19 Nov
MDW13:47Chicago Midway
25h 43m
2 stops
SYD08:30Sydney Kingsford Smith
$2,368
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Sydney to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 78,305 searches. Data last updated 17 October 2025.
Use the filters below to find and compare flights from Sydney to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/11

11:20-12:30

2 stops41h 10m

Chicago Midway

Sun 16/11

06:30-09:00

2 stops33h 30m

$1,729

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 26/12

10:40-16:24

2 stops22h 44m

Chicago Midway

Mon 2/2

09:30-08:30

2 stops30h 00m

$2,145

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Tue 3/2

13:05-06:50

2 stops24h 45m

$2,219

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 12/11

10:40-18:18

2 stops24h 38m

Chicago Midway

Wed 19/11

13:47-08:30

2 stops25h 43m

$2,368

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/12

10:40-22:22

2 stops28h 42m

Chicago Midway

Thu 22/1

13:00-06:50

2 stops24h 50m

$2,445

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 16/11

10:40-16:38

2 stops22h 58m

Chicago Midway

Sun 30/11

09:41-08:30

2 stops29h 49m

$2,456

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/11

10:40-17:43

2 stops24h 03m

Chicago Midway

Mon 17/11

10:47-08:30

2 stops28h 43m

$2,524

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 27/10

09:40-17:43

2 stops24h 03m

Chicago Midway

Sun 9/11

13:47-08:30

2 stops25h 43m

$2,531

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 1/11

09:40-17:55

2 stops24h 15m

Chicago Midway

Wed 19/11

09:34-08:30

2 stops29h 56m

$2,593

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 27/10

13:05-23:20

1 stop26h 15m

Chicago Midway

Sun 9/11

12:30-07:25

2 stops49h 55m

$2,596

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

How to get the cheapest flight ticket from Sydney to Chicago Midway Airport

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 airline that flies from Sydney Kingsford Smith to Chicago Midway?

Delta is the most popular carrier operating from Sydney Kingsford Smith to Chicago Midway

When to book flights from Sydney to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sydney to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated return price

Cheap Sydney to Chicago Midway Airport (SYD to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sydney to Chicago Midway Airport

Direct flights

None
There are no direct flights from Sydney to Chicago Midway Airport. There are no popular flight routes from Sydney to Chicago Midway Airport.
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  • How far is Sydney Kingsford Smith to Chicago Midway by plane?

    There are 14854.9 km between Sydney Kingsford Smith and Chicago Midway. Flights usually cover this in 20h 06m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Sydney Kingsford Smith Airport to Chicago Midway Airport?

    Prices for flights from Sydney Kingsford Smith Airport to Chicago Midway Airport refresh daily.

  • How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and stopovers. It is recommended that you verify with the airline you are booking with for travel from Sydney Kingsford Smith Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport 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 Midway Airport. 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 from Sydney to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Sydney to Chicago . Millions of users trust and use momondo every year so you are in good hands.

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?

momondo helps you find the best flight between Sydney and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Sydney are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago Midway Airport trip

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