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.

$887 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.

12:15 - 05:55SYD Sydney Kingsford Smith-MDW Chicago Midway

34h 40m2 stops Singapore Changi Los Angeles

15:45 - 17:55MDW Chicago Midway-SYD Sydney Kingsford Smith

33h 10m2 stops Los Angeles Singapore Changi

$3,798Singapore Airlines

Thu, 19 Nov - Wed, 2 Dec

14:05 - 07:23SYD Sydney Kingsford Smith-MDW Chicago Midway

34h 18m1 stop Dallas/Fort Worth

10:21 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 34m1 stop Dallas/Fort Worth

$3,999Multiple Airlines

Thu, 19 Nov - Wed, 2 Dec

14:05 - 00:01SYD Sydney Kingsford Smith-MDW Chicago Midway

26h 56m2 stops Dallas/Fort Worth Atlanta Hartsfield-Jackson

06:01 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

31h 54m1 stop Dallas/Fort Worth

$4,009Multiple Airlines

Wed, 23 Dec - Wed, 30 Dec

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

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

10:21 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 34m1 stop Dallas/Fort Worth

$4,038Multiple Airlines

Thu, 19 Nov - Wed, 2 Dec

14:05 - 19:42SYD Sydney Kingsford Smith-MDW Chicago Midway

46h 37m2 stops Dallas/Fort Worth Orlando

10:40 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

27h 15m1 stop Dallas/Fort Worth

$4,556Multiple Airlines

Sat, 5 Dec - Sat, 12 Dec

14:05 - 12:03SYD Sydney Kingsford Smith-MDW Chicago Midway

38h 58m1 stop Dallas/Fort Worth

13:11 - 17:45MDW Chicago Midway-SYD Sydney Kingsford Smith

35h 34m2 stops Atlanta Hartsfield-Jackson Abu Dhabi Zayed Intl

$5,219Multiple Airlines

Fri, 18 Dec - Fri, 1 Jan

09:45 - 00:01SYD Sydney Kingsford Smith-MDW Chicago Midway

31h 16m3 stops Auckland Intl Los Angeles Atlanta Hartsfield-Jackson

06:01 - 06:55MDW Chicago Midway-SYD Sydney Kingsford Smith

31h 54m1 stop Dallas/Fort Worth

$5,270Multiple Airlines

Fri, 18 Dec - Fri, 1 Jan

12:15 - 05:55SYD Sydney Kingsford Smith-MDW Chicago Midway

34h 40m2 stops Singapore Changi Los Angeles

15:45 - 21:15MDW Chicago Midway-SYD Sydney Kingsford Smith

36h 30m2 stops Los Angeles Singapore Changi

$5,670Singapore Airlines

Fri, 25 Dec - Thu, 31 Dec

12:15 - 05:55SYD Sydney Kingsford Smith-MDW Chicago Midway

34h 40m2 stops Singapore Changi Los Angeles

16:45 - 21:15MDW Chicago Midway-SYD Sydney Kingsford Smith

35h 30m2 stops Los Angeles Singapore Changi

$6,377Singapore Airlines

Sat, 19 Dec - Mon, 4 Jan

12:15 - 05:55SYD Sydney Kingsford Smith-MDW Chicago Midway

34h 40m2 stops Singapore Changi Los Angeles

10:00 - 17:55MDW Chicago Midway-SYD Sydney Kingsford Smith

38h 55m2 stops San Francisco Singapore Changi

$6,903Singapore Airlines

Sat, 2 Jan - Sat, 16 Jan

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Singapore Airlines flights from Sydney to Chicago Midway Airport

Our best Singapore Airlines deals on Sydney to Chicago Midway Airport flight tickets

Singapore Airlines

19 Nov

SYD12:15Sydney Kingsford Smith

34h 40m

2 stops

MDW05:55Chicago Midway

2 Dec

MDW15:45Chicago Midway

33h 10m

2 stops

SYD17:55Sydney Kingsford Smith

$3,798

Singapore Airlines

25 Dec

SYD12:15Sydney Kingsford Smith

34h 40m

2 stops

MDW05:55Chicago Midway

31 Dec

MDW15:45Chicago Midway

36h 30m

2 stops

SYD21:15Sydney Kingsford Smith

$5,670

Singapore Airlines

19 Dec

SYD12:15Sydney Kingsford Smith

34h 40m

2 stops

MDW05:55Chicago Midway

4 Jan

MDW16:45Chicago Midway

35h 30m

2 stops

SYD21:15Sydney Kingsford Smith

$6,377

WestJet flights from Sydney to Chicago Midway Airport

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

WestJet

23 Dec

SYD20:30Sydney Kingsford Smith

61h 54m

2 stops

MDW17:24Chicago Midway

30 Dec

MDW11:47Chicago Midway

49h 48m

2 stops

SYD06:35Sydney Kingsford Smith

$10,923

WestJet

21 Dec

SYD20:30Sydney Kingsford Smith

61h 54m

2 stops

MDW17:24Chicago Midway

4 Jan

MDW09:56Chicago Midway

51h 39m

2 stops

SYD06:35Sydney Kingsford Smith

$11,971

WestJet

17 Dec

SYD20:30Sydney Kingsford Smith

61h 54m

2 stops

MDW17:24Chicago Midway

1 Jan

MDW11:47Chicago Midway

49h 48m

2 stops

SYD06:35Sydney Kingsford Smith

$12,996

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

Thu 19/11

12:15-05:55

2 stops34h 40m

Chicago Midway

Wed 2/12

15:45-17:55

2 stops33h 10m

$3,798

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 19/11

14:05-07:23

1 stop34h 18m

Chicago Midway

Wed 2/12

10:21-06:55

1 stop27h 34m

$3,999

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Wed 23/12

14:05-00:01

2 stops26h 56m

Chicago Midway

Wed 30/12

06:01-06:55

1 stop31h 54m

$4,009

Fastest return journey

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Thu 19/11

14:05-23:47

2 stops26h 42m

Chicago Midway

Wed 2/12

10:21-06:55

1 stop27h 34m

$4,038

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 5/12

14:05-19:42

2 stops46h 37m

Chicago Midway

Sat 12/12

10:40-06:55

1 stop27h 15m

$4,556

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 18/12

14:05-12:03

1 stop38h 58m

Chicago Midway

Fri 1/1

13:11-17:45

2 stops35h 34m

$5,219

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 18/12

09:45-00:01

3 stops31h 16m

Chicago Midway

Fri 1/1

06:01-06:55

1 stop31h 54m

$5,270

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Fri 25/12

12:15-05:55

2 stops34h 40m

Chicago Midway

Thu 31/12

15:45-21:15

2 stops36h 30m

$5,670

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 19/12

12:15-05:55

2 stops34h 40m

Chicago Midway

Mon 4/1

16:45-21:15

2 stops35h 30m

$6,377

SydneyChicago

SYD Sydney Kingsford Smith - MDW Chicago Midway

SYDMDW

Sydney Kingsford Smith

Sat 2/1

12:15-05:55

2 stops34h 40m

Chicago Midway

Sat 16/1

10:00-17:55

2 stops38h 55m

$6,903

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Sydney to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Sydney Kingsford Smith to Chicago Midway?

Delta is the most popular carrier operating from Sydney Kingsford Smith to Chicago Midway

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	$887
Fastest flight time	29h 15m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $887. The best return flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $3,798.

The fastest flight from Sydney to Chicago Midway Airport takes 29h 15m

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 29h 15m, 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.

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.