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.

$1,060 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.

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

06:05 - 11:50

MDW

SYD

38h 45m

3 stops

$1,326Multiple Airlines

Mon, 3 Aug - Wed, 19 Aug

13:15 - 11:07

SYD

MDW

36h 52m

3 stops

11:06 - 11:50

MDW

SYD

33h 44m

3 stops

$1,351Multiple Airlines

Mon, 3 Aug - Thu, 6 Aug

09:10 - 20:32

SYD

MDW

26h 22m

2 stops

06:05 - 07:05

MDW

SYD

34h 00m

2 stops

$1,686Multiple Airlines

Thu, 6 Aug - Tue, 18 Aug

17:50 - 11:07

SYD

MDW

32h 17m

2 stops

11:06 - 07:05

MDW

SYD

28h 59m

2 stops

$1,695Multiple Airlines

Mon, 3 Aug - Thu, 6 Aug

17:50 - 11:07

SYD

MDW

32h 17m

2 stops

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$1,757Multiple Airlines

Mon, 3 Aug - Thu, 6 Aug

09:10 - 20:32

SYD

MDW

26h 22m

2 stops

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$1,770Multiple Airlines

Thu, 23 Jul - Wed, 5 Aug

12:00 - 16:51

SYD

MDW

19h 51m

1 stop

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$2,166Multiple Airlines

Tue, 28 Jul - Wed, 12 Aug

12:00 - 16:51

SYD

MDW

19h 51m

1 stop

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$2,212Multiple Airlines

Tue, 28 Jul - Sat, 15 Aug

12:00 - 16:51

SYD

MDW

19h 51m

1 stop

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$2,228Multiple Airlines

Tue, 28 Jul - Tue, 11 Aug

12:00 - 17:22

SYD

MDW

20h 22m

1 stop

11:06 - 07:30

MDW

SYD

29h 24m

2 stops

$2,248Multiple Airlines

Mon, 27 Jul - Wed, 12 Aug

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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

1 Oct

SYD09:15Sydney Kingsford Smith

24h 04m

2 stops

MDW18:19Chicago Midway

9 Oct

MDW09:29Chicago Midway

30h 21m

2 stops

SYD07:50Sydney Kingsford Smith

$2,468

Delta

1 Oct

SYD09:15Sydney Kingsford Smith

24h 04m

2 stops

MDW18:19Chicago Midway

9 Oct

MDW09:29Chicago Midway

30h 21m

2 stops

SYD07:50Sydney Kingsford Smith

$2,474

Delta

1 Oct

SYD09:15Sydney Kingsford Smith

28h 30m

2 stops

MDW22:45Chicago Midway

9 Oct

MDW13:28Chicago Midway

26h 22m

2 stops

SYD07:50Sydney Kingsford Smith

$2,521

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

Wed 19/8

06:05-11:50

3 stops38h 45m

$1,326

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

13:15-11:07

3 stops36h 52m

Chicago Midway

Thu 6/8

11:06-11:50

3 stops33h 44m

$1,351

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 6/8

09:10-20:32

2 stops26h 22m

Chicago Midway

Tue 18/8

06:05-07:05

2 stops34h 00m

$1,686

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

17:50-11:07

2 stops32h 17m

Chicago Midway

Thu 6/8

11:06-07:05

2 stops28h 59m

$1,695

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/8

17:50-11:07

2 stops32h 17m

Chicago Midway

Thu 6/8

11:06-07:30

2 stops29h 24m

$1,757

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 23/7

09:10-20:32

2 stops26h 22m

Chicago Midway

Wed 5/8

11:06-07:30

2 stops29h 24m

$1,770

Fastest return journey

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 28/7

12:00-16:51

1 stop19h 51m

Chicago Midway

Wed 12/8

11:06-07:30

2 stops29h 24m

$2,166

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 28/7

12:00-16:51

1 stop19h 51m

Chicago Midway

Sat 15/8

11:06-07:30

2 stops29h 24m

$2,212

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 28/7

12:00-16:51

1 stop19h 51m

Chicago Midway

Tue 11/8

11:06-07:30

2 stops29h 24m

$2,228

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 27/7

12:00-17:22

1 stop20h 22m

Chicago Midway

Wed 12/8

11:06-07:30

2 stops29h 24m

$2,248

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	19h 51m
Direct flights	None

The fastest flight from Sydney to Chicago Midway Airport takes 19h 51m

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 19h 51m, 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.