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Cheap flights from Chicago Midway Airport to Sydney from $537

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 5/28. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Sydney

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:00 am - 11:50 am
MDW
-
SYD
38h 50m
3 stops
Multiple Airlines Logo
1:15 pm - 2:12 pm
SYD
-
MDW
39h 57m
3 stops
$1,444Multiple Airlines
Sun, May 24 - Sun, May 31
Multiple Airlines Logo
6:10 am - 11:50 am
MDW
-
SYD
38h 40m
3 stops
Multiple Airlines Logo
1:15 pm - 11:09 am
SYD
-
MDW
36h 54m
3 stops
$1,562Multiple Airlines
Tue, Apr 28 - Sun, May 10
Delta Logo
1:49 pm - 6:50 am
MDW
-
SYD
26h 01m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,610Delta
Wed, Aug 5 - Sun, Aug 30
Delta Logo
1:05 pm - 6:50 am
MDW
-
SYD
26h 45m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,611Delta
Tue, Sep 1 - Tue, Sep 22
Delta Logo
10:59 am - 6:50 am
MDW
-
SYD
28h 51m
2 stops
Delta Logo
9:15 am - 6:18 pm
SYD
-
MDW
24h 03m
2 stops
$1,653Delta
Mon, Jun 1 - Mon, Jun 15
Delta Logo
9:17 am - 6:50 am
MDW
-
SYD
30h 33m
2 stops
Delta Logo
9:15 am - 6:18 pm
SYD
-
MDW
24h 03m
2 stops
$1,654Delta
Sun, Jun 28 - Mon, Jul 6
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
5:50 pm - 11:09 am
SYD
-
MDW
32h 19m
2 stops
$1,655Multiple Airlines
Sat, May 2 - Mon, May 11
Delta Logo
10:59 am - 6:50 am
MDW
-
SYD
28h 51m
2 stops
Delta Logo
9:15 am - 6:18 pm
SYD
-
MDW
24h 03m
2 stops
$1,660Delta
Mon, Jun 1 - Mon, Jun 15
Multiple Airlines Logo
6:10 am - 7:30 am
MDW
-
SYD
34h 20m
2 stops
Multiple Airlines Logo
5:50 pm - 11:09 am
SYD
-
MDW
32h 19m
2 stops
$1,676Multiple Airlines
Tue, Apr 21 - Sun, May 10
Delta Logo
9:30 am - 6:50 am
MDW
-
SYD
30h 20m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,684Delta
Sat, Aug 22 - Fri, Sep 4

Delta flights from Chicago Midway Airport to Sydney

Our best Delta deals on Chicago Midway Airport to Sydney flight tickets
Delta
Sep 1
MDW2:00 pmChicago Midway
25h 50m
2 stops
SYD6:50 amSydney Kingsford Smith
Sep 22
SYD9:15 amSydney Kingsford Smith
23h 50m
2 stops
MDW6:05 pmChicago Midway
$1,610
Delta
Sep 1
MDW1:05 pmChicago Midway
26h 45m
2 stops
SYD6:50 amSydney Kingsford Smith
Sep 8
SYD9:15 amSydney Kingsford Smith
24h 16m
2 stops
MDW6:31 pmChicago Midway
$1,611
Delta
Jun 1
MDW10:59 amChicago Midway
28h 51m
2 stops
SYD6:50 amSydney Kingsford Smith
Jun 15
SYD9:15 amSydney Kingsford Smith
24h 03m
2 stops
MDW6:18 pmChicago Midway
$1,653

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 April 6, 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

Cheapest round-trip

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 5/24

6:00 am-11:50 am

3 stops38h 50m

Sydney Kingsford Smith

Sun 5/31

1:15 pm-2:12 pm

3 stops39h 57m

$1,444

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 4/28

6:10 am-11:50 am

3 stops38h 40m

Sydney Kingsford Smith

Sun 5/10

1:15 pm-11:09 am

3 stops36h 54m

$1,562
Quickest round-trip

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Wed 8/5

1:49 pm-6:50 am

2 stops26h 01m

Sydney Kingsford Smith

Sun 8/30

9:15 am-6:31 pm

2 stops24h 16m

$1,610

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 9/1

1:05 pm-6:50 am

2 stops26h 45m

Sydney Kingsford Smith

Tue 9/22

9:15 am-6:31 pm

2 stops24h 16m

$1,611

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/1

10:59 am-6:50 am

2 stops28h 51m

Sydney Kingsford Smith

Mon 6/15

9:15 am-6:18 pm

2 stops24h 03m

$1,653

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sun 6/28

9:17 am-6:50 am

2 stops30h 33m

Sydney Kingsford Smith

Mon 7/6

9:15 am-6:18 pm

2 stops24h 03m

$1,654

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 5/2

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Mon 5/11

5:50 pm-11:09 am

2 stops32h 19m

$1,655

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/1

10:59 am-6:50 am

2 stops28h 51m

Sydney Kingsford Smith

Mon 6/15

9:15 am-6:18 pm

2 stops24h 03m

$1,660

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 4/21

6:10 am-7:30 am

2 stops34h 20m

Sydney Kingsford Smith

Sun 5/10

5:50 pm-11:09 am

2 stops32h 19m

$1,676

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Sat 8/22

9:30 am-6:50 am

2 stops30h 20m

Sydney Kingsford Smith

Fri 9/4

9:15 am-6:31 pm

2 stops24h 16m

$1,684

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 01m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sydney takes 26h 01m
There are no direct flights from Chicago Midway Airport to Sydney. There are no popular flight routes from Chicago Midway Airport to Sydney.
Search flight deals

Frequently asked questions about flying 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 01m 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
Penrith
Randwick
Coogee
Leura
Lithgow
Manly
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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