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.

$1,217 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.

10:15 - 16:47SYD Sydney Kingsford Smith-MDW Chicago Midway

22h 32m2 stops Los Angeles Minneapolis St Paul

13:27 - 07:20MDW Chicago Midway-SYD Sydney Kingsford Smith

25h 53m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,786Delta

Mon, 19 Oct - Mon, 26 Oct

10:40 - 16:50SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 10m2 stops Los Angeles Minneapolis St Paul

09:30 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

30h 00m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,807Delta

Wed, 2 Dec - Wed, 13 Jan

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

$2,855Delta

Thu, 5 Nov - Thu, 12 Nov

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

$2,861Delta

Thu, 5 Nov - Thu, 12 Nov

10:40 - 17:24SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 44m2 stops Los Angeles Minneapolis St Paul

09:30 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

30h 00m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,874Delta

Thu, 24 Dec - Sat, 9 Jan

10:15 - 16:47SYD Sydney Kingsford Smith-MDW Chicago Midway

22h 32m2 stops Los Angeles Minneapolis St Paul

09:29 - 07:20MDW Chicago Midway-SYD Sydney Kingsford Smith

29h 51m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,914Delta

Sat, 24 Oct - Sat, 31 Oct

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

23h 07m2 stops Los Angeles Minneapolis St Paul

11:27 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

28h 03m2 stops Atlanta Hartsfield-Jackson Los Angeles

$2,931Delta

Sat, 7 Nov - Sat, 14 Nov

10:40 - 18:00SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 20m2 stops Los Angeles Detroit Metropolitan Wayne County

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

27h 00m2 stops Minneapolis St Paul Los Angeles

$2,937Delta

Fri, 6 Nov - Fri, 13 Nov

10:40 - 17:24SYD Sydney Kingsford Smith-MDW Chicago Midway

23h 44m2 stops Los Angeles Minneapolis St Paul

13:00 - 08:30MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 30m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,955Delta

Thu, 24 Dec - Sun, 10 Jan

10:15 - 16:47SYD Sydney Kingsford Smith-MDW Chicago Midway

22h 32m2 stops Los Angeles Minneapolis St Paul

12:27 - 07:20MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 53m2 stops Minneapolis St Paul Los Angeles

$2,989Delta

Thu, 8 Oct - Sat, 24 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

09:30 - 23:44SYD Sydney Kingsford Smith-MDW Chicago Midway

29h 14m2 stops Los Angeles Atlanta Hartsfield-Jackson

06:25 - 07:55MDW Chicago Midway-SYD Sydney Kingsford Smith

33h 30m3 stops Atlanta Hartsfield-Jackson Los Angeles San Francisco

$2,875Multiple Airlines

Mon, 28 Sep - Tue, 6 Oct

09:15 - 22:44SYD Sydney Kingsford Smith-MDW Chicago Midway

28h 29m2 stops Los Angeles Atlanta Hartsfield-Jackson

09:29 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

30h 21m2 stops Detroit Metropolitan Wayne County Los Angeles

$2,938Delta

Thu, 1 Oct - Wed, 14 Oct

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

24h 04m2 stops Los Angeles Minneapolis St Paul

12:49 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 01m2 stops Atlanta Hartsfield-Jackson Los Angeles

$2,989Delta

Thu, 1 Oct - Thu, 15 Oct

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

24h 04m2 stops Los Angeles Minneapolis St Paul

12:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 23m2 stops Minneapolis St Paul Los Angeles

$3,008Delta

Thu, 1 Oct - Sat, 17 Oct

09:15 - 22:44SYD Sydney Kingsford Smith-MDW Chicago Midway

28h 29m2 stops Los Angeles Atlanta Hartsfield-Jackson

12:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 23m2 stops Minneapolis St Paul Los Angeles

$3,016Delta

Thu, 1 Oct - Fri, 9 Oct

09:15 - 22:44SYD Sydney Kingsford Smith-MDW Chicago Midway

28h 29m2 stops Los Angeles Atlanta Hartsfield-Jackson

13:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 23m2 stops Detroit Metropolitan Wayne County Los Angeles

$3,040Delta

Thu, 1 Oct - Sat, 17 Oct

09:30 - 23:44SYD Sydney Kingsford Smith-MDW Chicago Midway

29h 14m2 stops Los Angeles Atlanta Hartsfield-Jackson

06:25 - 08:00MDW Chicago Midway-SYD Sydney Kingsford Smith

33h 35m2 stops Atlanta Hartsfield-Jackson Los Angeles

$3,063Multiple Airlines

Mon, 28 Sep - Tue, 6 Oct

09:15 - 22:44SYD Sydney Kingsford Smith-MDW Chicago Midway

28h 29m2 stops Los Angeles Atlanta Hartsfield-Jackson

12:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 23m2 stops Minneapolis St Paul Los Angeles

$3,610Delta

Thu, 1 Oct - Fri, 9 Oct

09:15 - 18:33SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 18m2 stops Los Angeles Detroit Metropolitan Wayne County

13:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 23m2 stops Detroit Metropolitan Wayne County Los Angeles

$9,822Delta

Thu, 1 Oct - Fri, 9 Oct

09:15 - 18:33SYD Sydney Kingsford Smith-MDW Chicago Midway

24h 18m2 stops Los Angeles Detroit Metropolitan Wayne County

13:27 - 07:50MDW Chicago Midway-SYD Sydney Kingsford Smith

26h 23m2 stops Detroit Metropolitan Wayne County Los Angeles

$9,825Delta

Thu, 1 Oct - Fri, 9 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

19 Oct

SYD10:15Sydney Kingsford Smith

22h 32m

2 stops

MDW16:47Chicago Midway

26 Oct

MDW13:27Chicago Midway

25h 53m

2 stops

SYD07:20Sydney Kingsford Smith

$2,786

Delta

2 Dec

SYD10:40Sydney Kingsford Smith

23h 10m

2 stops

MDW16:50Chicago Midway

13 Jan

MDW09:30Chicago Midway

30h 00m

2 stops

SYD08:30Sydney Kingsford Smith

$2,807

Delta

5 Nov

SYD10:40Sydney Kingsford Smith

23h 07m

2 stops

MDW16:47Chicago Midway

12 Nov

MDW13:05Chicago Midway

26h 25m

2 stops

SYD08:30Sydney Kingsford Smith

$2,855

Korean Air flights from Sydney to Chicago Midway Airport

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

Korean Air

8 Oct

SYD08:55Sydney Kingsford Smith

29h 38m

2 stops

MDW22:33Chicago Midway

24 Oct

MDW16:19Chicago Midway

35h 46m

2 stops

SYD20:05Sydney Kingsford Smith

$8,979

Korean Air

19 Oct

SYD08:55Sydney Kingsford Smith

29h 38m

2 stops

MDW22:33Chicago Midway

21 Oct

MDW09:29Chicago Midway

29h 51m

2 stops

SYD07:20Sydney Kingsford Smith

$19,043

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

Mon 19/10

10:15-16:47

2 stops22h 32m

Chicago Midway

Mon 26/10

13:27-07:20

2 stops25h 53m

$2,786

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 2/12

10:40-16:50

2 stops23h 10m

Chicago Midway

Wed 13/1

09:30-08:30

2 stops30h 00m

$2,807

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 5/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Thu 12/11

13:05-08:30

2 stops26h 25m

$2,855

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 5/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Thu 12/11

13:05-08:30

2 stops26h 25m

$2,861

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 24/12

10:40-17:24

2 stops23h 44m

Chicago Midway

Sat 9/1

09:30-08:30

2 stops30h 00m

$2,874

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 24/10

10:15-16:47

2 stops22h 32m

Chicago Midway

Sat 31/10

09:29-07:20

2 stops29h 51m

$2,914

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 7/11

10:40-16:47

2 stops23h 07m

Chicago Midway

Sat 14/11

11:27-08:30

2 stops28h 03m

$2,931

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 6/11

10:40-18:00

2 stops24h 20m

Chicago Midway

Fri 13/11

12:30-08:30

2 stops27h 00m

$2,937

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 24/12

10:40-17:24

2 stops23h 44m

Chicago Midway

Sun 10/1

13:00-08:30

2 stops26h 30m

$2,955

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 8/10

10:15-16:47

2 stops22h 32m

Chicago Midway

Sat 24/10

12:27-07:20

2 stops26h 53m

$2,989

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	$1,217
Fastest flight time	22h 32m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $1,217. The best return flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $2,786.

The fastest flight from Sydney to Chicago Midway Airport takes 22h 32m

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 32m, 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.