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.

$723 Cheap Flights from Sydney to Chicago Midway Airport in 2026/27

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.

10:40 - 16:54SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 14m2 stops Los Angeles Atlanta Hartsfield-Jackson

09:56 - 06:50MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 54m2 stops Minneapolis St Paul Los Angeles

$2,453Delta

Tue, 19 Jan - Tue, 26 Jan

10:40 - 22:54SYD Sydney Kingsford Smith-MDW Chicago Midway

29h 14m2 stops Los Angeles Atlanta Hartsfield-Jackson

13:41 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

25h 49m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,828Delta

Thu, 26 Nov - Thu, 3 Dec

10:40 - 22:54SYD Sydney Kingsford Smith-MDW Chicago Midway

29h 14m2 stops Los Angeles Atlanta Hartsfield-Jackson

12:30 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 00m2 stops Minneapolis St Paul Los Angeles

$2,978Delta

Mon, 9 Nov - Thu, 12 Nov

14:05 - 11:22SYD Sydney Kingsford Smith-MDW Chicago Midway

38h 17m1 stop Dallas/Fort Worth

12:20 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

25h 35m1 stop Dallas/Fort Worth

$3,554Multiple Airlines

Mon, 9 Nov - Thu, 12 Nov

14:05 - 23:47SYD Sydney Kingsford Smith-MDW Chicago Midway

26h 42m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson

12:20 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

25h 35m1 stop Dallas/Fort Worth

$3,756Multiple Airlines

Mon, 9 Nov - Thu, 12 Nov

20:30 - 12:51SYD Sydney Kingsford Smith-MDW Chicago Midway

33h 21m3 stops Vancouver Intl Toronto Pearson Intl Detroit Metropolitan Wayne County

18:44 - 20:50MDW Chicago Midway-SYD Sydney Kingsford Smith

33h 06m3 stops Detroit Metropolitan Wayne County Toronto Pearson Intl Hong Kong Intl

$4,518Multiple Airlines

Mon, 9 Nov - Thu, 12 Nov

20:30 - 12:51SYD Sydney Kingsford Smith-MDW Chicago Midway

33h 21m3 stops Vancouver Intl Toronto Pearson Intl Detroit Metropolitan Wayne County

09:30 - 09:35MDW Chicago Midway-SYD Sydney Kingsford Smith

31h 05m2 stops Detroit Metropolitan Wayne County Toronto Pearson Intl

$4,704Multiple Airlines

Mon, 9 Nov - Thu, 12 Nov

14:05 - 10:05SYD Sydney Kingsford Smith-MDW Chicago Midway

37h 00m1 stop Dallas/Fort Worth

17:30 - 06:35MDW Chicago Midway-SYD Sydney Kingsford Smith

44h 05m2 stops Minneapolis St Paul Vancouver Intl

$6,144Multiple Airlines

Thu, 10 Dec - Thu, 17 Dec

21:55 - 11:25SYD Sydney Kingsford Smith-MDW Chicago Midway

30h 30m2 stops Incheon Intl Detroit Metropolitan Wayne County

16:08 - 20:05MDW Chicago Midway-SYD Sydney Kingsford Smith

34h 57m2 stops Atlanta Hartsfield-Jackson Incheon Intl

$8,541Multiple Airlines

Wed, 25 Nov - Sat, 5 Dec

21:55 - 12:04SYD Sydney Kingsford Smith-MDW Chicago Midway

31h 09m2 stops Incheon Intl Atlanta Hartsfield-Jackson

17:12 - 20:05MDW Chicago Midway-SYD Sydney Kingsford Smith

33h 53m2 stops Atlanta Hartsfield-Jackson Incheon Intl

$8,834Multiple Airlines

Mon, 7 Dec - Mon, 14 Dec

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customise your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Sydney to Chicago Midway Airport

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

Delta

19 Jan

SYD10:40Sydney Kingsford Smith

23h 14m

2 stops

MDW16:54Chicago Midway

26 Jan

MDW09:56Chicago Midway

27h 54m

2 stops

SYD06:50Sydney Kingsford Smith

$2,453

Delta

26 Nov

SYD10:40Sydney Kingsford Smith

29h 14m

2 stops

MDW22:54Chicago Midway

3 Dec

MDW13:41Chicago Midway

25h 49m

2 stops

SYD08:30Sydney Kingsford Smith

$2,828

Delta

5 Nov

SYD10:40Sydney Kingsford Smith

28h 53m

2 stops

MDW22:33Chicago Midway

8 Nov

MDW12:49Chicago Midway

26h 41m

2 stops

SYD08:30Sydney Kingsford Smith

$2,894

Korean Air flights from Sydney to Chicago Midway Airport

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

Korean Air

2 Nov

SYD21:55Sydney Kingsford Smith

31h 52m

2 stops

MDW12:47Chicago Midway

9 Nov

MDW17:13Chicago Midway

33h 52m

2 stops

SYD20:05Sydney Kingsford Smith

$8,515

Korean Air

15 Jan

SYD21:55Sydney Kingsford Smith

41h 22m

2 stops

MDW22:17Chicago Midway

26 Jan

MDW17:45Chicago Midway

33h 20m

2 stops

SYD20:05Sydney Kingsford Smith

$8,884

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

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Tue 19/1

10:40-16:54

2 stops23h 14m

Chicago Midway

Tue 26/1

09:56-06:50

2 stops27h 54m

$2,453

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 26/11

10:40-22:54

2 stops29h 14m

Chicago Midway

Thu 3/12

13:41-08:30

2 stops25h 49m

$2,828

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

10:40-22:54

2 stops29h 14m

Chicago Midway

Thu 12/11

12:30-08:30

2 stops27h 00m

$2,978

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

14:05-11:22

1 stop38h 17m

Chicago Midway

Thu 12/11

12:20-06:55

1 stop25h 35m

$3,554

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

14:05-23:47

2 stops26h 42m

Chicago Midway

Thu 12/11

12:20-06:55

1 stop25h 35m

$3,756

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

20:30-12:51

3 stops33h 21m

Chicago Midway

Thu 12/11

18:44-20:50

3 stops33h 06m

$4,518

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 9/11

20:30-12:51

3 stops33h 21m

Chicago Midway

Thu 12/11

09:30-09:35

2 stops31h 05m

$4,704

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 10/12

14:05-10:05

1 stop37h 00m

Chicago Midway

Thu 17/12

17:30-06:35

2 stops44h 05m

$6,144

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 25/11

21:55-11:25

2 stops30h 30m

Chicago Midway

Sat 5/12

16:08-20:05

2 stops34h 57m

$8,541

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Mon 7/12

21:55-12:04

2 stops31h 09m

Chicago Midway

Mon 14/12

17:12-20:05

2 stops33h 53m

$8,834

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

Best price found	$723
Fastest flight time	22h 34m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $723. The best return flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $2,453.

The fastest flight from Sydney to Chicago Midway Airport takes 22h 34m

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 22h 34m, 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.