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.

$833 Cheap Flights from Sydney to Chicago Midway Airport in 2026

Find the cheapest flights from Sydney to Chicago

Return

One-way

Last minute

Cheap return flights

Enter your travel dates to find the best prices.

09:30 - 20:31SYD Sydney Kingsford Smith-MDW Chicago Midway

26h 01m2 stops Los Angeles Dallas/Fort Worth

21:26 - 07:00MDW Chicago Midway-SYD Sydney Kingsford Smith

42h 34m2 stops Dallas/Fort Worth Los Angeles

$1,975Multiple Airlines

Mon, 24 Aug - Thu, 27 Aug

12:00 - 20:31SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 31m1 stop Dallas/Fort Worth

06:25 - 07:30MDW Chicago Midway-SYD Sydney Kingsford Smith

34h 05m2 stops Atlanta Hartsfield-Jackson Los Angeles

$2,363Multiple Airlines

Sun, 6 Sep - Sat, 19 Sep

10:40 - 16:47SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 07m2 stops Los Angeles Minneapolis St Paul

13:05 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 25m2 stops Atlanta Hartsfield-Jackson Los Angeles

$2,451Delta

Tue, 3 Nov - Mon, 1 Feb

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

13:19 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 31m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,742Delta

Tue, 22 Sep - Tue, 29 Sep

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

13:19 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 31m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,747Delta

Tue, 8 Sep - Tue, 22 Sep

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

14:00 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

25h 50m2 stops Minneapolis St Paul Los Angeles

$2,751Delta

Wed, 23 Sep - Wed, 30 Sep

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

13:19 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 31m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,795Delta

Tue, 8 Sep - Fri, 18 Sep

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

13:19 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 31m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,799Delta

Thu, 10 Sep - Thu, 17 Sep

09:15 - 15:57SYD Sydney Kingsford Smith-MDW Chicago Midway

21h 42m2 stops Los Angeles Minneapolis St Paul

09:29 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

30h 21m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,846Delta

Sun, 6 Sep - Sat, 19 Sep

09:15 - 18:19SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 04m2 stops Los Angeles Minneapolis St Paul

13:00 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 50m2 stops Atlanta Hartsfield-Jackson Los Angeles

$2,850Delta

Wed, 9 Sep - Tue, 15 Sep

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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

3 Nov

SYD10:40Sydney Kingsford Smith

23h 07m

2 stops

MDW16:47Chicago Midway

1 Feb

MDW13:05Chicago Midway

26h 25m

2 stops

SYD08:30Sydney Kingsford Smith

$2,451

Delta

22 Sept

SYD09:15Sydney Kingsford Smith

24h 04m

2 stops

MDW18:19Chicago Midway

29 Sept

MDW13:19Chicago Midway

26h 31m

2 stops

SYD06:50Sydney Kingsford Smith

$2,742

Delta

8 Sept

SYD09:15Sydney Kingsford Smith

24h 04m

2 stops

MDW18:19Chicago Midway

22 Sept

MDW13:19Chicago Midway

26h 31m

2 stops

SYD06:50Sydney Kingsford Smith

$2,747

Korean Air flights from Sydney to Chicago Midway Airport

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

Korean Air

23 Sept

SYD07:55Sydney Kingsford Smith

29h 49m

2 stops

MDW22:44Chicago Midway

30 Sept

MDW09:29Chicago Midway

29h 51m

2 stops

SYD06:20Sydney Kingsford Smith

$8,536

Korean Air

19 Oct

SYD08:55Sydney Kingsford Smith

29h 38m

2 stops

MDW22:33Chicago Midway

26 Oct

MDW17:15Chicago Midway

34h 50m

2 stops

SYD20:05Sydney Kingsford Smith

$19,005

Korean Air

10 Jan

SYD21:55Sydney Kingsford Smith

31h 01m

2 stops

MDW11:56Chicago Midway

20 Jan

MDW17:25Chicago Midway

33h 40m

2 stops

SYD20:05Sydney Kingsford Smith

$19,707

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 Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 24/8

09:30-20:31

2 stops26h 01m

Chicago Midway

Thu 27/8

21:26-07:00

2 stops42h 34m

$1,975

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 6/9

12:00-20:31

1 stop23h 31m

Chicago Midway

Sat 19/9

06:25-07:30

2 stops34h 05m

$2,363

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 3/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Mon 1/2

13:05-08:30

2 stops26h 25m

$2,451

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 22/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 29/9

13:19-06:50

2 stops26h 31m

$2,742

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 22/9

13:19-06:50

2 stops26h 31m

$2,747

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 23/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Wed 30/9

14:00-06:50

2 stops25h 50m

$2,751

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 8/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Fri 18/9

13:19-06:50

2 stops26h 31m

$2,795

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 10/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Thu 17/9

13:19-06:50

2 stops26h 31m

$2,799

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sun 6/9

09:15-15:57

2 stops21h 42m

Chicago Midway

Sat 19/9

09:29-06:50

2 stops30h 21m

$2,846

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 9/9

09:15-18:19

2 stops24h 04m

Chicago Midway

Tue 15/9

13:00-06:50

2 stops26h 50m

$2,850

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	24h 04m
Direct flights	None

The fastest flight from Sydney to Chicago Midway Airport takes 24h 04m

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 24h 04m, 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.