Cheap flights from Chicago Midway Airport to Sydney from $664

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 3/3. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:15 am - 9:00 am
MDW
-
SYD
33h 45m
2 stops
Multiple Airlines Logo
11:20 am - 11:44 pm
SYD
-
MDW
29h 24m
2 stops
$1,423Multiple Airlines
Wed, Feb 11 - Mon, Feb 23
Multiple Airlines Logo
6:00 am - 7:25 am
MDW
-
SYD
32h 25m
2 stops
Multiple Airlines Logo
11:20 am - 11:41 pm
SYD
-
MDW
29h 21m
2 stops
$1,454Multiple Airlines
Tue, Feb 17 - Fri, Feb 27
Delta Logo
1:26 pm - 8:30 am
MDW
-
SYD
26h 04m
2 stops
Delta Logo
9:40 am - 5:54 pm
SYD
-
MDW
24h 14m
2 stops
$1,469Delta
Tue, Feb 10 - Tue, Mar 17
Delta Logo
1:26 pm - 8:30 am
MDW
-
SYD
26h 04m
2 stops
Delta Logo
10:40 am - 5:37 pm
SYD
-
MDW
23h 57m
2 stops
$1,470Delta
Tue, Feb 10 - Tue, Mar 3
Delta Logo
2:05 pm - 7:30 am
MDW
-
SYD
25h 25m
2 stops
Delta Logo
10:15 am - 8:53 am
SYD
-
MDW
38h 38m
2 stops
$1,488Delta
Tue, Mar 17 - Tue, Mar 31
Delta Logo
9:53 am - 8:30 am
MDW
-
SYD
29h 37m
2 stops
Delta Logo
10:40 am - 6:40 pm
SYD
-
MDW
25h 00m
2 stops
$1,519Delta
Wed, Feb 11 - Fri, Feb 27
Delta Logo
9:53 am - 8:30 am
MDW
-
SYD
29h 37m
2 stops
Delta Logo
10:40 am - 5:45 pm
SYD
-
MDW
24h 05m
2 stops
$1,520Delta
Wed, Feb 11 - Fri, Feb 27
Delta Logo
2:05 pm - 7:30 am
MDW
-
SYD
25h 25m
2 stops
Delta Logo
10:15 am - 8:53 am
SYD
-
MDW
38h 38m
2 stops
$1,538Delta
Thu, Mar 19 - Wed, Apr 1
Delta Logo
1:26 pm - 8:30 am
MDW
-
SYD
26h 04m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,569Delta
Thu, Feb 5 - Sat, May 16
Delta Logo
1:26 pm - 6:50 am
MDW
-
SYD
24h 24m
2 stops
Delta Logo
1:15 pm - 10:31 pm
SYD
-
MDW
25h 16m
2 stops
$1,570Delta
Thu, Feb 5 - Thu, Mar 12

Delta flights from Chicago Midway Airport to Sydney

Our best Delta deals on Chicago Midway Airport to Sydney flight tickets
Delta
Feb 3
MDW1:26 pmChicago Midway
24h 24m
2 stops
SYD6:50 amSydney Kingsford Smith
Mar 10
SYD9:40 amSydney Kingsford Smith
25h 00m
2 stops
MDW6:40 pmChicago Midway
$1,469
Delta
Feb 3
MDW12:46 pmChicago Midway
25h 04m
2 stops
SYD6:50 amSydney Kingsford Smith
Mar 10
SYD9:40 amSydney Kingsford Smith
24h 14m
2 stops
MDW5:54 pmChicago Midway
$1,470
Delta
Mar 17
MDW2:05 pmChicago Midway
25h 25m
2 stops
SYD7:30 amSydney Kingsford Smith
Mar 31
SYD10:15 amSydney Kingsford Smith
38h 38m
2 stops
MDW8:53 amChicago Midway
$1,488

WestJet flights from Chicago Midway Airport to Sydney

Our best WestJet deals on Chicago Midway Airport to Sydney flight tickets
WestJet
Feb 4
MDW1:51 pmChicago Midway
47h 44m
2 stops
SYD6:35 amSydney Kingsford Smith
Mar 9
SYD8:30 pmSydney Kingsford Smith
56h 55m
2 stops
MDW1:25 pmChicago Midway
$7,843
WestJet
Feb 4
MDW7:16 pmChicago Midway
42h 19m
2 stops
SYD6:35 amSydney Kingsford Smith
Mar 9
SYD8:30 pmSydney Kingsford Smith
56h 55m
2 stops
MDW1:25 pmChicago Midway
$7,851
WestJet
Feb 1
MDW7:16 pmChicago Midway
42h 19m
2 stops
SYD6:35 amSydney Kingsford Smith
Mar 9
SYD8:30 pmSydney Kingsford Smith
56h 55m
2 stops
MDW1:25 pmChicago Midway
$8,239

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 January 21, 2026.
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

Wed 2/11

6:15 am-9:00 am

2 stops33h 45m

Sydney Kingsford Smith

Mon 2/23

11:20 am-11:44 pm

2 stops29h 24m

$1,423

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/17

6:00 am-7:25 am

2 stops32h 25m

Sydney Kingsford Smith

Fri 2/27

11:20 am-11:41 pm

2 stops29h 21m

$1,454

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/10

1:26 pm-8:30 am

2 stops26h 04m

Sydney Kingsford Smith

Tue 3/17

9:40 am-5:54 pm

2 stops24h 14m

$1,469

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 2/10

1:26 pm-8:30 am

2 stops26h 04m

Sydney Kingsford Smith

Tue 3/3

10:40 am-5:37 pm

2 stops23h 57m

$1,470

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 3/17

2:05 pm-7:30 am

2 stops25h 25m

Sydney Kingsford Smith

Tue 3/31

10:15 am-8:53 am

2 stops38h 38m

$1,488

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 2/11

9:53 am-8:30 am

2 stops29h 37m

Sydney Kingsford Smith

Fri 2/27

10:40 am-6:40 pm

2 stops25h 00m

$1,519

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 2/11

9:53 am-8:30 am

2 stops29h 37m

Sydney Kingsford Smith

Fri 2/27

10:40 am-5:45 pm

2 stops24h 05m

$1,520

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 3/19

2:05 pm-7:30 am

2 stops25h 25m

Sydney Kingsford Smith

Wed 4/1

10:15 am-8:53 am

2 stops38h 38m

$1,538

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 2/5

1:26 pm-8:30 am

2 stops26h 04m

Sydney Kingsford Smith

Sat 5/16

9:15 am-6:31 pm

2 stops24h 16m

$1,569

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 2/5

1:26 pm-6:50 am

2 stops24h 24m

Sydney Kingsford Smith

Thu 3/12

1:15 pm-10:31 pm

2 stops25h 16m

$1,570

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Sydney from

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 airline that flies from Chicago Midway to Sydney Kingsford Smith?

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

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

Fastest flight time

26h 05m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sydney takes 26h 05m
There are no direct flights from Chicago Midway Airport to Sydney. There are no popular flight routes from Chicago Midway Airport to Sydney.
  • 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 26h 05m 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
Coogee
Manly
Lithgow
Leura
Penrith
Cronulla
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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1 adult
Fri 2/20
Fri 2/27

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