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Cheap flights from Sydney to Chicago from $1,320

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sydney to Chicago departing on 15/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap return flights

Enter your travel dates to find the best prices.
Delta Logo
09:40 - 16:53
SYD
-
MDW
23h 13m2 stops
Delta Logo
13:09 - 06:35
MDW
-
SYD
26h 26m2 stops
$2,071Delta
Wed, 25 Mar - Mon, 6 Apr
Delta Logo
09:15 - 21:45
SYD
-
MDW
27h 30m2 stops
Delta Logo
13:05 - 06:35
MDW
-
SYD
26h 30m2 stops
$2,259Delta
Fri, 12 Jun - Sun, 12 Jul
Delta Logo
14:15 - 22:22
SYD
-
MDW
25h 07m2 stops
Delta Logo
13:51 - 08:30
MDW
-
SYD
25h 39m2 stops
$2,370Delta
Mon, 2 Feb - Mon, 9 Feb
Delta Logo
09:15 - 18:31
SYD
-
MDW
24h 16m2 stops
Delta Logo
13:05 - 06:35
MDW
-
SYD
26h 30m2 stops
$2,372Delta
Fri, 12 Jun - Sun, 12 Jul
Delta Logo
14:15 - 22:22
SYD
-
MDW
25h 07m2 stops
Delta Logo
13:29 - 06:50
MDW
-
SYD
24h 21m2 stops
$2,596Delta
Mon, 9 Feb - Thu, 12 Feb
Multiple Airlines Logo
14:05 - 13:09
SYD
-
MDW
40h 04m1 stop
Multiple Airlines Logo
08:15 - 06:55
MDW
-
SYD
53h 40m2 stops
$6,407Multiple Airlines
Fri, 2 Jan - Mon, 5 Jan
Multiple Airlines Logo
20:30 - 15:20
SYD
-
MDW
35h 50m3 stops
Multiple Airlines Logo
11:05 - 09:35
MDW
-
SYD
29h 30m3 stops
$7,346Multiple Airlines
Fri, 2 Jan - Mon, 5 Jan
Delta Logo
10:40 - 22:22
SYD
-
MDW
28h 42m2 stops
Delta Logo
13:49 - 08:30
MDW
-
SYD
25h 41m2 stops
$8,180Delta
Fri, 2 Jan - Mon, 5 Jan
Multiple Airlines Logo
09:10 - 22:31
SYD
-
MDW
30h 21m2 stops
Multiple Airlines Logo
09:35 - 06:55
MDW
-
SYD
29h 20m2 stops
$17,570Multiple Airlines
Thu, 12 Feb - Thu, 12 Mar
Korean Air Logo
09:10 - 22:22
SYD
-
MDW
30h 12m2 stops
Korean Air Logo
06:00 - 06:55
MDW
-
SYD
31h 55m2 stops
$19,010Korean Air
Tue, 10 Feb - Tue, 24 Feb

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
25 Mar
SYD09:40Sydney Kingsford Smith
23h 13m
2 stops
MDW16:53Chicago Midway
6 Apr
MDW13:09Chicago Midway
26h 26m
2 stops
SYD06:35Sydney Kingsford Smith
$2,071
Find similar
Delta
12 June
SYD09:15Sydney Kingsford Smith
27h 30m
2 stops
MDW21:45Chicago Midway
12 July
MDW13:05Chicago Midway
26h 30m
2 stops
SYD06:35Sydney Kingsford Smith
$2,259
Find similar
Delta
2 Feb
SYD14:15Sydney Kingsford Smith
25h 07m
2 stops
MDW22:22Chicago Midway
9 Feb
MDW13:51Chicago Midway
25h 39m
2 stops
SYD08:30Sydney Kingsford Smith
$2,370
Find similar

momondo Fare Finder

 
Customise your flight search to find flights from Sydney to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 78,305 searches. Data last updated 21 December 2025.
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

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 25/3

09:40-16:53

2 stops23h 13m

Chicago Midway

Mon 6/4

13:09-06:35

2 stops26h 26m

$2,071

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/6

09:15-21:45

2 stops27h 30m

Chicago Midway

Sun 12/7

13:05-06:35

2 stops26h 30m

$2,259

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

14:15-22:22

2 stops25h 07m

Chicago Midway

Mon 9/2

13:51-08:30

2 stops25h 39m

$2,370

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 12/6

09:15-18:31

2 stops24h 16m

Chicago Midway

Sun 12/7

13:05-06:35

2 stops26h 30m

$2,372

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 9/2

14:15-22:22

2 stops25h 07m

Chicago Midway

Thu 12/2

13:29-06:50

2 stops24h 21m

$2,596

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 2/1

14:05-13:09

1 stop40h 04m

Chicago Midway

Mon 5/1

08:15-06:55

2 stops53h 40m

$6,407

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 2/1

20:30-15:20

3 stops35h 50m

Chicago Midway

Mon 5/1

11:05-09:35

3 stops29h 30m

$7,346

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 2/1

10:40-22:22

2 stops28h 42m

Chicago Midway

Mon 5/1

13:49-08:30

2 stops25h 41m

$8,180

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 12/2

09:10-22:31

2 stops30h 21m

Chicago Midway

Thu 12/3

09:35-06:55

2 stops29h 20m

$17,570

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 10/2

09:10-22:22

2 stops30h 12m

Chicago Midway

Tue 24/2

06:00-06:55

2 stops31h 55m

$19,010

Flights are sorted by cheapest return flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
1
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See travel insights to Chicago from

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

Fastest flight time

23h 13m

Direct flights

None
The fastest flight from Sydney to Chicago Midway Airport takes 23h 13m
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

  • 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 23h 13m, 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.

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