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Cheap flights from Chicago Midway Airport to Sydney from $542

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Sydney departing on 10/20. 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 Chicago Midway Airport to Sydney

Cheap round-trip flights

Multiple Airlines Logo
12:03 pm - 9:00 amMDW-SYD
28h 57m2 stops
Multiple Airlines Logo
2:05 pm - 10:03 pmSYD-MDW
24h 58m2 stops
$1,033Multiple Airlines
Find Deal
Mon, Oct 27 - Sun, Nov 9
Multiple Airlines Logo
9:44 am - 8:05 amMDW-SYD
30h 21m2 stops
Multiple Airlines Logo
2:05 pm - 11:03 pmSYD-MDW
24h 58m2 stops
$1,072Multiple Airlines
Find Deal
Mon, Oct 20 - Sun, Nov 2
Multiple Airlines Logo
6:30 am - 9:00 amMDW-SYD
34h 30m2 stops
Multiple Airlines Logo
11:20 am - 11:30 amSYD-MDW
41h 10m2 stops
$1,411Multiple Airlines
Find Deal
Thu, Oct 30 - Thu, Nov 6
Delta Logo
12:47 pm - 8:30 amMDW-SYD
26h 43m2 stops
Delta Logo
10:40 am - 4:38 pmSYD-MDW
22h 58m2 stops
$1,467Delta
Find Deal
Mon, Nov 10 - Sun, Nov 23
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
Delta Logo
9:40 am - 6:08 pmSYD-MDW
24h 28m2 stops
$1,468Delta
Find Deal
Mon, Feb 9 - Sun, Mar 22
Delta Logo
11:48 am - 8:30 amMDW-SYD
27h 42m2 stops
Delta Logo
10:40 am - 9:46 pmSYD-MDW
28h 06m2 stops
$1,517Delta
Find Deal
Wed, Dec 31 - Fri, Jan 30
Delta Logo
9:30 am - 8:30 amMDW-SYD
30h 00m2 stops
Delta Logo
10:40 am - 6:08 pmSYD-MDW
24h 28m2 stops
$1,518Delta
Find Deal
Wed, Feb 11 - Fri, Feb 27
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
Delta Logo
10:25 am - 6:34 pmSYD-MDW
24h 09m2 stops
$1,542Delta
Find Deal
Wed, Jan 21 - Wed, Apr 1
Delta Logo
9:54 am - 6:50 amMDW-SYD
27h 56m2 stops
Delta Logo
2:15 pm - 9:46 pmSYD-MDW
24h 31m2 stops
$1,567Delta
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Thu, Jan 1 - Sat, Jan 17
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
Delta Logo
9:40 am - 6:34 pmSYD-MDW
24h 54m2 stops
$1,568Delta
Find Deal
Fri, Feb 27 - Fri, Mar 13

Delta flights from Chicago Midway Airport to Sydney

Our best Delta deals on Chicago Midway Airport to Sydney flight tickets
Delta
Nov 10
MDW12:47 pmChicago Midway
26h 43m
2 stops
SYD8:30 amSydney Kingsford Smith
Nov 23
SYD10:40 amSydney Kingsford Smith
22h 58m
2 stops
MDW4:38 pmChicago Midway
$1,467
Find similar
Delta
Feb 9
MDW1:00 pmChicago Midway
26h 30m
2 stops
SYD8:30 amSydney Kingsford Smith
Mar 22
SYD9:40 amSydney Kingsford Smith
24h 28m
2 stops
MDW6:08 pmChicago Midway
$1,468
Find similar
Delta
Dec 31
MDW11:48 amChicago Midway
27h 42m
2 stops
SYD8:30 amSydney Kingsford Smith
Jan 30
SYD10:40 amSydney Kingsford Smith
28h 06m
2 stops
MDW9:46 pmChicago Midway
$1,517
Find similar

LATAM Airlines flights from Chicago Midway Airport to Sydney

Our best LATAM Airlines deals on Chicago Midway Airport to Sydney flight tickets
LATAM Airlines
Sep 28
MDW10:35 amChicago Midway
56h 00m
3 stops
SYD9:35 amSydney Kingsford Smith
Oct 1
SYD11:50 amSydney Kingsford Smith
44h 45m
3 stops
MDW5:35 pmChicago Midway
$4,984
Find similar
LATAM Airlines
Sep 26
MDW10:35 amChicago Midway
56h 00m
3 stops
SYD9:35 amSydney Kingsford Smith
Sep 29
SYD11:50 amSydney Kingsford Smith
36h 50m
3 stops
MDW9:40 amChicago Midway
$6,475
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Sydney 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 832,500 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Sydney that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 10/27

12:03 pm-9:00 am

2 stops28h 57m

Sydney Kingsford Smith

Sun 11/9

2:05 pm-10:03 pm

2 stops24h 58m

$1,033

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 10/20

9:44 am-8:05 am

2 stops30h 21m

Sydney Kingsford Smith

Sun 11/2

2:05 pm-11:03 pm

2 stops24h 58m

$1,072

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 10/30

6:30 am-9:00 am

2 stops34h 30m

Sydney Kingsford Smith

Thu 11/6

11:20 am-11:30 am

2 stops41h 10m

$1,411

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 11/10

12:47 pm-8:30 am

2 stops26h 43m

Sydney Kingsford Smith

Sun 11/23

10:40 am-4:38 pm

2 stops22h 58m

$1,467

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 2/9

1:00 pm-8:30 am

2 stops26h 30m

Sydney Kingsford Smith

Sun 3/22

9:40 am-6:08 pm

2 stops24h 28m

$1,468

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 12/31

11:48 am-8:30 am

2 stops27h 42m

Sydney Kingsford Smith

Fri 1/30

10:40 am-9:46 pm

2 stops28h 06m

$1,517

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 2/11

9:30 am-8:30 am

2 stops30h 00m

Sydney Kingsford Smith

Fri 2/27

10:40 am-6:08 pm

2 stops24h 28m

$1,518

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 1/21

1:00 pm-8:30 am

2 stops26h 30m

Sydney Kingsford Smith

Wed 4/1

10:25 am-6:34 pm

2 stops24h 09m

$1,542

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 1/1

9:54 am-6:50 am

2 stops27h 56m

Sydney Kingsford Smith

Sat 1/17

2:15 pm-9:46 pm

2 stops24h 31m

$1,567

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 2/27

1:00 pm-8:30 am

2 stops26h 30m

Sydney Kingsford Smith

Fri 3/13

9:40 am-6:34 pm

2 stops24h 54m

$1,568

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Sydney

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 day to depart on your flight to Sydney?

The cheapest day to depart from Chicago Midway Airport to Sydney is on a Saturday when prices can be found for as low as $1,166. The most expensive day to fly to Sydney is Thursday, with ticket prices averaging around $1,391.

What is the cheapest time of day to depart on your flight to Sydney?

According to our data, the cheapest time of day to fly to Sydney is in the morning. momondo users have found flights departing from Chicago Midway Airport to Sydney in the morning for as low as $1,224. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Flights to Sydney are more costly in the evening, with an average ticket price of $1,412. Departure times in the evening fall within the peak daily travel times, which is why tickets can be more expensive.

When to book flights from Chicago Midway Airport to Sydney

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

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

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

Direct flights

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

    There are 9230.4 mi between Chicago Midway and Sydney Kingsford Smith. Typically, this will take 24h 30m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to Sydney Kingsford Smith Airport are refreshed on a daily basis.

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Sydney Kingsford Smith Airport.

  • What documentation or ID do you need to fly to Sydney Kingsford Smith Airport?

    The necessary travel and health documents for your Sydney Kingsford Smith Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Sydney?

Book flights to Sydney if you plan to visit one of these locations
Parramatta
Bondi Beach
Katoomba
Wollongong
Randwick
Cronulla
Coogee
Lithgow
Penrith
Manly
Leura
Charlestown
Terrigal
Swansea

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Sydney?

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

Can I find flights from Chicago to Sydney with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Sydney flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Sydney?

Once you have performed a search for Chicago to Sydney flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Of course. momondo tracks the price of Chicago to Sydney flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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