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Cheap flights from Chicago Midway Airport to Sydney from $509

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 5/9. 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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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
6:10 am - 7:05 am
MDW
-
SYD
33h 55m
2 stops
Multiple Airlines Logo
9:10 am - 2:12 pm
SYD
-
MDW
44h 02m
2 stops
$1,349Multiple Airlines
Tue, Apr 28 - Sun, May 17
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
5:50 pm - 2:12 pm
SYD
-
MDW
35h 22m
2 stops
$1,354Multiple Airlines
Tue, May 5 - Sun, May 31
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,383Multiple Airlines
Tue, May 19 - Tue, Jun 2
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,387Multiple Airlines
Fri, May 1 - Wed, May 13
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
5:50 pm - 2:12 pm
SYD
-
MDW
35h 22m
2 stops
$1,396Multiple Airlines
Tue, May 5 - Sun, May 17
Multiple Airlines Logo
8:26 am - 7:30 am
MDW
-
SYD
32h 04m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,472Multiple Airlines
Thu, Apr 23 - Sun, May 10
Delta Logo
1:22 pm - 6:50 am
MDW
-
SYD
26h 28m
2 stops
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
$1,610Delta
Thu, May 28 - Mon, Jun 8
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
$1,611Delta
Mon, Jun 1 - Mon, Jun 15
Delta Logo
12:45 pm - 6:50 am
MDW
-
SYD
27h 05m
2 stops
Delta Logo
9:15 am - 10:15 pm
SYD
-
MDW
28h 00m
2 stops
$1,613Delta
Mon, Jun 29 - Mon, Jul 13
Multiple Airlines Logo
6:00 am - 7:05 am
MDW
-
SYD
34h 05m
2 stops
Multiple Airlines Logo
9:10 am - 11:09 am
SYD
-
MDW
40h 59m
2 stops
$1,638Multiple Airlines
Tue, May 12 - Thu, May 28

Delta flights from Chicago Midway Airport to Sydney

Our best Delta deals on Chicago Midway Airport to Sydney flight tickets
Delta
May 28
MDW1:22 pmChicago Midway
26h 28m
2 stops
SYD6:50 amSydney Kingsford Smith
Jun 8
SYD9:15 amSydney Kingsford Smith
24h 16m
2 stops
MDW6:31 pmChicago Midway
$1,610
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
$1,611
Delta
Jun 29
MDW12:45 pmChicago Midway
27h 05m
2 stops
SYD6:50 amSydney Kingsford Smith
Jul 13
SYD9:15 amSydney Kingsford Smith
28h 00m
2 stops
MDW10:15 pmChicago Midway
$1,613

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 12, 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

Tue 4/28

6:10 am-7:05 am

2 stops33h 55m

Sydney Kingsford Smith

Sun 5/17

9:10 am-2:12 pm

2 stops44h 02m

$1,349

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 5/5

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Sun 5/31

5:50 pm-2:12 pm

2 stops35h 22m

$1,354

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 5/19

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Tue 6/2

9:10 am-11:09 am

2 stops40h 59m

$1,383

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Fri 5/1

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Wed 5/13

9:10 am-11:09 am

2 stops40h 59m

$1,387

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 5/5

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Sun 5/17

5:50 pm-2:12 pm

2 stops35h 22m

$1,396

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 4/23

8:26 am-7:30 am

2 stops32h 04m

Sydney Kingsford Smith

Sun 5/10

9:10 am-11:09 am

2 stops40h 59m

$1,472
Quickest round-trip

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Thu 5/28

1:22 pm-6:50 am

2 stops26h 28m

Sydney Kingsford Smith

Mon 6/8

9:15 am-6:31 pm

2 stops24h 16m

$1,610

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

$1,611

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Mon 6/29

12:45 pm-6:50 am

2 stops27h 05m

Sydney Kingsford Smith

Mon 7/13

9:15 am-10:15 pm

2 stops28h 00m

$1,613

ChicagoSydney

MDW - SYD

MDWSYD

Chicago Midway

Tue 5/12

6:00 am-7:05 am

2 stops34h 05m

Sydney Kingsford Smith

Thu 5/28

9:10 am-11:09 am

2 stops40h 59m

$1,638

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 28m

Direct flights

None
The fastest flight from Chicago Midway Airport to Sydney takes 26h 28m
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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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 28m 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.

Frequently asked questions about flying from Chicago Midway Airport to Sydney

  • How do I get Price Alerts for flights from Chicago Midway Airport to Sydney?

    Price Alerts will notify you by email when the price for flights to Sydney from Chicago Midway Airport decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

  • How can I save money on flights from Chicago Midway Airport to Sydney with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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
Leura
Randwick
Coogee
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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