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Cheap flights from Sydney to Chicago from $1,324

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

Delta Logo
10:25 - 18:25SYD-MDW
24h 00m2 stops
Delta Logo
11:10 - 07:35MDW-SYD
28h 25m2 stops
$2,153Delta
Find Deal
Thu, 9 Oct - Sat, 18 Oct
Delta Logo
10:40 - 18:34SYD-MDW
24h 54m2 stops
Delta Logo
10:35 - 08:30MDW-SYD
28h 55m2 stops
$2,303Delta
Find Deal
Tue, 13 Jan - Wed, 28 Jan
Delta Logo
09:25 - 17:37SYD-MDW
23h 12m2 stops
Delta Logo
10:31 - 06:35MDW-SYD
29h 04m2 stops
$2,527Delta
Find Deal
Wed, 3 Sep - Tue, 9 Sep
Delta Logo
10:25 - 17:43SYD-MDW
23h 18m2 stops
Delta Logo
06:00 - 07:30MDW-SYD
33h 30m2 stops
$2,529Delta
Find Deal
Thu, 23 Oct - Mon, 27 Oct
Delta Logo
09:25 - 17:35SYD-MDW
23h 10m2 stops
Delta Logo
12:48 - 07:35MDW-SYD
26h 47m2 stops
$2,643Delta
Find Deal
Mon, 15 Sep - Mon, 6 Oct
Delta Logo
09:25 - 17:35SYD-MDW
23h 10m2 stops
Delta Logo
09:35 - 06:35MDW-SYD
30h 00m2 stops
$2,717Delta
Find Deal
Thu, 18 Sep - Thu, 25 Sep
Delta Logo
09:25 - 18:35SYD-MDW
24h 10m2 stops
Delta Logo
09:35 - 07:35MDW-SYD
30h 00m2 stops
$2,778Delta
Find Deal
Sat, 27 Sep - Tue, 7 Oct
Delta Logo
09:25 - 21:36SYD-MDW
27h 11m2 stops
Delta Logo
10:35 - 06:35MDW-SYD
29h 00m2 stops
$2,869Delta
Find Deal
Fri, 19 Sep - Fri, 26 Sep
LATAM Airlines Logo
11:50 - 11:48SYD-MDW
38h 58m3 stops
LATAM Airlines Logo
10:35 - 17:15MDW-SYD
38h 40m2 stops
$5,475LATAM Airlines
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Mon, 15 Sep - Mon, 6 Oct
Logo
07:55 - 13:36SYD-MDW
44h 41m2 stops
Logo
09:20 - 06:20MDW-SYD
30h 00m2 stops
$17,207
Find Deal
Mon, 1 Sep - Fri, 12 Sep

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
9 Oct
SYD10:25Sydney Kingsford Smith
24h 00m
2 stops
MDW18:25Chicago Midway
18 Oct
MDW11:10Chicago Midway
28h 25m
2 stops
SYD07:35Sydney Kingsford Smith
$2,153
Find similar
Delta
13 Jan
SYD10:40Sydney Kingsford Smith
24h 54m
2 stops
MDW18:34Chicago Midway
28 Jan
MDW10:35Chicago Midway
28h 55m
2 stops
SYD08:30Sydney Kingsford Smith
$2,303
Find similar
Delta
11 Aug
SYD09:25Sydney Kingsford Smith
23h 22m
2 stops
MDW17:47Chicago Midway
3 Sept
MDW13:08Chicago Midway
26h 27m
2 stops
SYD06:35Sydney Kingsford Smith
$2,524
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 6 August 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

Thu 9/10

10:25-18:25

2 stops24h 00m

Chicago Midway

Sat 18/10

11:10-07:35

2 stops28h 25m

$2,153

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 13/1

10:40-18:34

2 stops24h 54m

Chicago Midway

Wed 28/1

10:35-08:30

2 stops28h 55m

$2,303

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 3/9

09:25-17:37

2 stops23h 12m

Chicago Midway

Tue 9/9

10:31-06:35

2 stops29h 04m

$2,527

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 23/10

10:25-17:43

2 stops23h 18m

Chicago Midway

Mon 27/10

06:00-07:30

2 stops33h 30m

$2,529

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 15/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Mon 6/10

12:48-07:35

2 stops26h 47m

$2,643

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 18/9

09:25-17:35

2 stops23h 10m

Chicago Midway

Thu 25/9

09:35-06:35

2 stops30h 00m

$2,717

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 27/9

09:25-18:35

2 stops24h 10m

Chicago Midway

Tue 7/10

09:35-07:35

2 stops30h 00m

$2,778

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 19/9

09:25-21:36

2 stops27h 11m

Chicago Midway

Fri 26/9

10:35-06:35

2 stops29h 00m

$2,869

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 15/9

11:50-11:48

3 stops38h 58m

Chicago Midway

Mon 6/10

10:35-17:15

2 stops38h 40m

$5,475

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 1/9

07:55-13:36

2 stops44h 41m

Chicago Midway

Fri 12/9

09:20-06:20

2 stops30h 00m

$17,207

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, Korean Air, and WestJet 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

Best price found

$1,324

Fastest flight time

23h 10m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $1,324. The best return flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $2,153.
The fastest flight from Sydney to Chicago Midway Airport takes 23h 10m
There are no direct flights from Sydney to Chicago Midway Airport. Popular non-direct route for this connection is Sydney Kingsford Smith Airport - 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 23h 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

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