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Cheap flights from Sydney to Chicago from $716

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 15/10. 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

Logo
10:10 - 13:38SYD-MDW
43h 28m2 stops
Logo
05:10 - 08:05MDW-SYD
34h 55m2 stops
$1,432
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Mon, 13 Oct - Mon, 20 Oct
Logo
11:20 - 12:37SYD-MDW
41h 17m2 stops
Logo
06:25 - 07:25MDW-SYD
32h 00m2 stops
$1,450
Find Deal
Thu, 30 Oct - Thu, 6 Nov
Delta Logo
09:25 - 18:35SYD-MDW
24h 10m2 stops
Delta Logo
13:14 - 08:30MDW-SYD
26h 16m2 stops
$1,507Delta
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Tue, 30 Sep - Wed, 12 Nov
Delta Logo
09:40 - 22:14SYD-MDW
28h 34m2 stops
Delta Logo
13:08 - 08:30MDW-SYD
26h 22m2 stops
$1,820Delta
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Wed, 29 Oct - Wed, 5 Nov
Delta Logo
09:40 - 17:43SYD-MDW
24h 03m2 stops
Delta Logo
09:20 - 08:30MDW-SYD
30h 10m2 stops
$2,012Delta
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Thu, 30 Oct - Thu, 6 Nov
Delta Logo
10:40 - 18:25SYD-MDW
24h 45m2 stops
Delta Logo
09:32 - 08:30MDW-SYD
29h 58m2 stops
$2,218Delta
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Sat, 8 Nov - Sat, 22 Nov
Delta Logo
10:25 - 17:43SYD-MDW
23h 18m2 stops
Delta Logo
09:35 - 07:35MDW-SYD
30h 00m2 stops
$2,235Delta
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Wed, 8 Oct - Tue, 14 Oct
Logo
14:05 - 21:28SYD-MDW
24h 23m1 stop
Logo
06:00 - 07:25MDW-SYD
32h 25m2 stops
$2,403
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Fri, 12 Dec - Fri, 23 Jan
Delta Logo
09:40 - 16:09SYD-MDW
22h 29m2 stops
Delta Logo
10:40 - 08:30MDW-SYD
28h 50m2 stops
$2,442Delta
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Thu, 30 Oct - Thu, 6 Nov
Korean Air Logo
07:55 - 12:28SYD-MDW
43h 33m2 stops
Korean Air Logo
09:35 - 06:55MDW-SYD
29h 20m2 stops
$16,305Korean Air
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Tue, 30 Sep - Thu, 30 Oct

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
30 Sept
SYD09:25Sydney Kingsford Smith
24h 10m
2 stops
MDW18:35Chicago Midway
12 Nov
MDW13:14Chicago Midway
26h 16m
2 stops
SYD08:30Sydney Kingsford Smith
$1,507
Find similar
Delta
29 Oct
SYD09:40Sydney Kingsford Smith
28h 34m
2 stops
MDW22:14Chicago Midway
5 Nov
MDW13:08Chicago Midway
26h 22m
2 stops
SYD08:30Sydney Kingsford Smith
$1,820
Find similar
Delta
30 Oct
SYD09:40Sydney Kingsford Smith
24h 03m
2 stops
MDW17:43Chicago Midway
6 Nov
MDW09:20Chicago Midway
30h 10m
2 stops
SYD08:30Sydney Kingsford Smith
$2,012
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 16 September 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

Mon 13/10

10:10-13:38

2 stops43h 28m

Chicago Midway

Mon 20/10

05:10-08:05

2 stops34h 55m

$1,432

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/10

11:20-12:37

2 stops41h 17m

Chicago Midway

Thu 6/11

06:25-07:25

2 stops32h 00m

$1,450

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Wed 12/11

13:14-08:30

2 stops26h 16m

$1,507

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 29/10

09:40-22:14

2 stops28h 34m

Chicago Midway

Wed 5/11

13:08-08:30

2 stops26h 22m

$1,820

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/10

09:40-17:43

2 stops24h 03m

Chicago Midway

Thu 6/11

09:20-08:30

2 stops30h 10m

$2,012

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 8/11

10:40-18:25

2 stops24h 45m

Chicago Midway

Sat 22/11

09:32-08:30

2 stops29h 58m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 8/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Tue 14/10

09:35-07:35

2 stops30h 00m

$2,235

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/12

14:05-21:28

1 stop24h 23m

Chicago Midway

Fri 23/1

06:00-07:25

2 stops32h 25m

$2,403

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/10

09:40-16:09

2 stops22h 29m

Chicago Midway

Thu 6/11

10:40-08:30

2 stops28h 50m

$2,442

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 30/9

07:55-12:28

2 stops43h 33m

Chicago Midway

Thu 30/10

09:35-06:55

2 stops29h 20m

$16,305

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, LATAM Airlines, and Korean Air are the most popular carriers 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 10m, 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

We make it super easy to schedule, organise and travel with friends or family. Trips is free – and available to use no matter where you book.
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