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Cheap flights from Sydney to Chicago from $1,542

This is the cheapest return flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 8/12. 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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Multiple Airlines Logo
11:20 - 08:46SYD-MDW
38h 26m2 stops
Multiple Airlines Logo
06:12 - 09:00MDW-SYD
33h 48m2 stops
$1,542Multiple Airlines
Find Deal
Mon, 8 Dec - Wed, 31 Dec
Multiple Airlines Logo
17:45 - 09:52SYD-MDW
33h 07m2 stops
Multiple Airlines Logo
06:12 - 09:00MDW-SYD
33h 48m2 stops
$1,628Multiple Airlines
Find Deal
Sun, 7 Dec - Wed, 31 Dec
Delta Logo
10:40 - 23:40SYD-MDW
30h 00m2 stops
Delta Logo
09:41 - 08:30MDW-SYD
29h 49m2 stops
$1,751Delta
Find Deal
Sun, 23 Nov - Sun, 30 Nov
Delta Logo
10:40 - 23:47SYD-MDW
30h 07m2 stops
Delta Logo
09:59 - 08:30MDW-SYD
29h 31m2 stops
$2,139Delta
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Tue, 9 Dec - Sun, 14 Dec
Delta Logo
10:40 - 17:19SYD-MDW
23h 39m2 stops
Delta Logo
13:49 - 08:30MDW-SYD
25h 41m2 stops
$2,184Delta
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Thu, 25 Dec - Thu, 22 Jan
Delta Logo
10:40 - 17:19SYD-MDW
23h 39m2 stops
Delta Logo
13:49 - 08:30MDW-SYD
25h 41m2 stops
$2,186Delta
Find Deal
Thu, 25 Dec - Thu, 22 Jan
Delta Logo
09:25 - 18:31SYD-MDW
24h 06m2 stops
Delta Logo
10:35 - 06:35MDW-SYD
29h 00m2 stops
$2,543Delta
Find Deal
Thu, 23 Apr - Wed, 29 Apr
Delta Logo
09:25 - 18:05SYD-MDW
23h 40m2 stops
Delta Logo
13:00 - 06:35MDW-SYD
26h 35m2 stops
$2,695Delta
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Fri, 24 Apr - Thu, 30 Apr
Delta Logo
10:40 - 16:18SYD-MDW
22h 38m2 stops
Delta Logo
06:00 - 08:30MDW-SYD
33h 30m2 stops
$3,191Delta
Find Deal
Sun, 14 Dec - Fri, 2 Jan
Delta Logo
10:40 - 23:47SYD-MDW
30h 07m2 stops
Delta Logo
06:00 - 08:30MDW-SYD
33h 30m2 stops
$3,210Delta
Find Deal
Sun, 14 Dec - Fri, 2 Jan

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
13 Nov
SYD10:40Sydney Kingsford Smith
24h 38m
2 stops
MDW18:18Chicago Midway
26 Nov
MDW09:34Chicago Midway
29h 56m
2 stops
SYD08:30Sydney Kingsford Smith
$1,523
Find similar
Delta
23 Nov
SYD10:40Sydney Kingsford Smith
30h 00m
2 stops
MDW23:40Chicago Midway
30 Nov
MDW09:41Chicago Midway
29h 49m
2 stops
SYD08:30Sydney Kingsford Smith
$1,751
Find similar
Delta
9 Dec
SYD10:40Sydney Kingsford Smith
30h 07m
2 stops
MDW23:47Chicago Midway
14 Dec
MDW09:59Chicago Midway
29h 31m
2 stops
SYD08:30Sydney Kingsford Smith
$2,139
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 5 November 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 8/12

11:20-08:46

2 stops38h 26m

Chicago Midway

Wed 31/12

06:12-09:00

2 stops33h 48m

$1,542

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 7/12

17:45-09:52

2 stops33h 07m

Chicago Midway

Wed 31/12

06:12-09:00

2 stops33h 48m

$1,628

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 23/11

10:40-23:40

2 stops30h 00m

Chicago Midway

Sun 30/11

09:41-08:30

2 stops29h 49m

$1,751

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 9/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Sun 14/12

09:59-08:30

2 stops29h 31m

$2,139

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Thu 22/1

13:49-08:30

2 stops25h 41m

$2,184

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

10:40-17:19

2 stops23h 39m

Chicago Midway

Thu 22/1

13:49-08:30

2 stops25h 41m

$2,186

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 23/4

09:25-18:31

2 stops24h 06m

Chicago Midway

Wed 29/4

10:35-06:35

2 stops29h 00m

$2,543

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 24/4

09:25-18:05

2 stops23h 40m

Chicago Midway

Thu 30/4

13:00-06:35

2 stops26h 35m

$2,695

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-16:18

2 stops22h 38m

Chicago Midway

Fri 2/1

06:00-08:30

2 stops33h 30m

$3,191

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 14/12

10:40-23:47

2 stops30h 07m

Chicago Midway

Fri 2/1

06:00-08:30

2 stops33h 30m

$3,210

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 22h 38m, 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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