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Cheap flights from Sydney to Chicago from $979

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 15/4. 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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Cheap return flights

Enter your travel dates to find the best prices.
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
12:53 - 06:50
MDW
-
SYD
26h 57m
2 stops
$1,711Delta
Thu, 19 Mar - Tue, 21 Apr
Delta Logo
09:40 - 18:40
SYD
-
MDW
25h 00m
2 stops
Delta Logo
13:23 - 06:50
MDW
-
SYD
26h 27m
2 stops
$1,715Delta
Thu, 19 Mar - Tue, 21 Apr
Multiple Airlines Logo
13:05 - 20:21
SYD
-
MDW
23h 16m
1 stop
Multiple Airlines Logo
21:16 - 06:55
MDW
-
SYD
41h 39m
1 stop
$1,959Multiple Airlines
Sat, 21 Mar - Sat, 28 Mar
Multiple Airlines Logo
13:05 - 20:21
SYD
-
MDW
23h 16m
1 stop
Multiple Airlines Logo
21:16 - 06:55
MDW
-
SYD
41h 39m
1 stop
$1,971Multiple Airlines
Sat, 21 Mar - Sat, 28 Mar
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
18:45 - 06:50
MDW
-
SYD
45h 05m
2 stops
$2,068Delta
Thu, 18 Jun - Mon, 20 Jul
Delta Logo
09:40 - 17:54
SYD
-
MDW
24h 14m
2 stops
Delta Logo
10:45 - 06:50
MDW
-
SYD
29h 05m
2 stops
$2,125Delta
Fri, 27 Mar - Mon, 6 Apr
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
18:45 - 06:50
MDW
-
SYD
45h 05m
2 stops
$2,143Delta
Fri, 19 Jun - Mon, 20 Jul
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
18:45 - 06:50
MDW
-
SYD
45h 05m
2 stops
$2,181Delta
Wed, 24 Jun - Sat, 18 Jul
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
18:45 - 06:50
MDW
-
SYD
45h 05m
2 stops
$2,218Delta
Fri, 19 Jun - Fri, 17 Jul
Delta Logo
09:15 - 08:38
SYD
-
MDW
38h 23m
2 stops
Delta Logo
18:45 - 06:50
MDW
-
SYD
45h 05m
2 stops
$2,255Delta
Wed, 24 Jun - Fri, 17 Jul

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
19 Mar
SYD09:40Sydney Kingsford Smith
24h 14m
2 stops
MDW17:54Chicago Midway
21 Apr
MDW12:53Chicago Midway
26h 57m
2 stops
SYD06:50Sydney Kingsford Smith
$1,711
Delta
19 Mar
SYD09:40Sydney Kingsford Smith
25h 00m
2 stops
MDW18:40Chicago Midway
21 Apr
MDW13:23Chicago Midway
26h 27m
2 stops
SYD06:50Sydney Kingsford Smith
$1,715
Delta
18 June
SYD09:15Sydney Kingsford Smith
38h 27m
2 stops
MDW08:42Chicago Midway
18 July
MDW14:00Chicago Midway
49h 50m
2 stops
SYD06:50Sydney Kingsford Smith
$2,068

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 4 February 2026.
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

Thu 19/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Tue 21/4

12:53-06:50

2 stops26h 57m

$1,711

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 19/3

09:40-18:40

2 stops25h 00m

Chicago Midway

Tue 21/4

13:23-06:50

2 stops26h 27m

$1,715

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 21/3

13:05-20:21

1 stop23h 16m

Chicago Midway

Sat 28/3

21:16-06:55

1 stop41h 39m

$1,959

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 21/3

13:05-20:21

1 stop23h 16m

Chicago Midway

Sat 28/3

21:16-06:55

1 stop41h 39m

$1,971

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 18/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Mon 20/7

18:45-06:50

2 stops45h 05m

$2,068

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 27/3

09:40-17:54

2 stops24h 14m

Chicago Midway

Mon 6/4

10:45-06:50

2 stops29h 05m

$2,125

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 19/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Mon 20/7

18:45-06:50

2 stops45h 05m

$2,143

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Sat 18/7

18:45-06:50

2 stops45h 05m

$2,181

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 19/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Fri 17/7

18:45-06:50

2 stops45h 05m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 24/6

09:15-08:38

2 stops38h 23m

Chicago Midway

Fri 17/7

18:45-06:50

2 stops45h 05m

$2,255

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

Fastest flight time

24h 05m

Direct flights

None
The fastest flight from Sydney to Chicago Midway Airport takes 24h 05m
There are no direct flights from Sydney to Chicago Midway Airport. There are no popular flight routes from Sydney to Chicago Midway Airport.
Search flight deals

  • 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 24h 05m, 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.

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