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

Search flight deals from Sydney to Chicago Midway Airport . While viewing offers you’ll have the option to create a Price Alert.

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

Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

How does momondo find its flight prices?

We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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.

$1,047 Cheap Flights from Sydney to Chicago Midway Airport in 2026

Find the cheapest flights from Sydney to Chicago

Return

One-way

Cheap return flights

Enter your travel dates to find the best prices.

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

11:06 - 22:25

MDW

SYD

44h 19m

3 stops

$1,346Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

11:06 - 22:25

MDW

SYD

44h 19m

3 stops

$1,381Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

06:05 - 22:25

MDW

SYD

49h 20m

3 stops

$1,395Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

13:15 - 10:58

SYD

MDW

36h 43m

3 stops

07:25 - 22:25

MDW

SYD

48h 00m

3 stops

$1,494Multiple Airlines

Sun, 13 Sep - Sun, 20 Sep

17:50 - 11:07

SYD

MDW

32h 17m

2 stops

06:05 - 07:30

MDW

SYD

34h 25m

2 stops

$1,830Multiple Airlines

Mon, 3 Aug - Mon, 10 Aug

09:10 - 20:32

SYD

MDW

26h 22m

2 stops

06:05 - 07:30

MDW

SYD

34h 25m

2 stops

$1,870Multiple Airlines

Thu, 6 Aug - Sun, 9 Aug

09:10 - 20:32

SYD

MDW

26h 22m

2 stops

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$1,933Multiple Airlines

Thu, 30 Jul - Fri, 14 Aug

10:40 - 22:10

SYD

MDW

28h 30m

2 stops

13:05 - 08:30

MDW

SYD

26h 25m

2 stops

$2,444Delta

Mon, 7 Dec - Tue, 29 Dec

10:40 - 16:20

SYD

MDW

22h 40m

2 stops

13:05 - 08:30

MDW

SYD

26h 25m

2 stops

$2,445Delta

Wed, 4 Nov - Wed, 11 Nov

10:15 - 16:39

SYD

MDW

22h 24m

2 stops

09:59 - 07:50

MDW

SYD

29h 51m

2 stops

$2,480Delta

Sat, 10 Oct - Mon, 19 Oct

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Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets

Delta

7 Dec

SYD10:40Sydney Kingsford Smith

28h 30m

2 stops

MDW22:10Chicago Midway

29 Dec

MDW13:05Chicago Midway

26h 25m

2 stops

SYD08:30Sydney Kingsford Smith

$2,444

Delta

4 Nov

SYD10:40Sydney Kingsford Smith

22h 40m

2 stops

MDW16:20Chicago Midway

11 Nov

MDW13:05Chicago Midway

26h 25m

2 stops

SYD08:30Sydney Kingsford Smith

$2,445

Delta

10 Oct

SYD10:15Sydney Kingsford Smith

22h 24m

2 stops

MDW16:39Chicago Midway

19 Oct

MDW09:59Chicago Midway

29h 51m

2 stops

SYD07:50Sydney Kingsford Smith

$2,480

Korean Air flights from Sydney to Chicago Midway Airport

Our best Korean Air deals on Sydney to Chicago Midway Airport flight tickets

Korean Air

20 July

SYD07:55Sydney Kingsford Smith

29h 20m

2 stops

MDW22:15Chicago Midway

12 Aug

MDW09:59Chicago Midway

29h 21m

2 stops

SYD06:20Sydney Kingsford Smith

$8,509

Korean Air

31 Aug

SYD07:55Sydney Kingsford Smith

29h 41m

2 stops

MDW22:36Chicago Midway

7 Sept

MDW09:59Chicago Midway

29h 21m

2 stops

SYD06:20Sydney Kingsford Smith

$8,514

Korean Air

4 Nov

SYD09:10Sydney Kingsford Smith

43h 55m

2 stops

MDW12:05Chicago Midway

8 Nov

MDW06:00Chicago Midway

31h 55m

2 stops

SYD06:55Sydney Kingsford Smith

$8,846

momondo Fare Finder

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

Cheapest return flight

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

11:06-22:25

3 stops44h 19m

$1,346

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

11:06-22:25

3 stops44h 19m

$1,381

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Mon 10/8

06:05-22:25

3 stops49h 20m

$1,395

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 13/9

13:15-10:58

3 stops36h 43m

Chicago Midway

Sun 20/9

07:25-22:25

3 stops48h 00m

$1,494

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

17:50-11:07

2 stops32h 17m

Chicago Midway

Mon 10/8

06:05-07:30

2 stops34h 25m

$1,830

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

09:10-20:32

2 stops26h 22m

Chicago Midway

Sun 9/8

06:05-07:30

2 stops34h 25m

$1,870

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 30/7

09:10-20:32

2 stops26h 22m

Chicago Midway

Fri 14/8

11:06-07:30

2 stops29h 24m

$1,933

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 7/12

10:40-22:10

2 stops28h 30m

Chicago Midway

Tue 29/12

13:05-08:30

2 stops26h 25m

$2,444

Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 4/11

10:40-16:20

2 stops22h 40m

Chicago Midway

Wed 11/11

13:05-08:30

2 stops26h 25m

$2,445

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 10/10

10:15-16:39

2 stops22h 24m

Chicago Midway

Mon 19/10

09:59-07:50

2 stops29h 51m

$2,480

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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	23h 46m
Direct flights	None

The fastest flight from Sydney to Chicago Midway Airport takes 23h 46m

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

Frequently asked questions about flying from Sydney to Chicago Midway Airport

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 23h 46m, 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.

Frequently asked questions about flying from Sydney to Chicago Midway Airport

How do I get Price Alerts for flights from Sydney to Chicago Midway Airport?
Search flight deals from Sydney to Chicago Midway Airport. While viewing offers you’ll have the option to create a Price Alert.
How can I save money on flights from Sydney to Chicago Midway Airport with momondo?
Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.
How does momondo find its flight prices?
We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

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.