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Cheap flights from Sydney to Chicago from $1,179

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 18/3. 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
09:25 - 21:45SYD-MDW
27h 20m2 stops
Delta Logo
14:00 - 06:35MDW-SYD
25h 35m2 stops
$2,065Delta
Find Deal
Wed, 29 Apr - Mon, 11 May
Delta Logo
10:40 - 17:34SYD-MDW
23h 54m2 stops
Delta Logo
09:50 - 08:30MDW-SYD
29h 40m2 stops
$2,085Delta
Find Deal
Mon, 12 Jan - Mon, 19 Jan
Delta Logo
09:25 - 18:05SYD-MDW
23h 40m2 stops
Delta Logo
14:00 - 06:35MDW-SYD
25h 35m2 stops
$2,140Delta
Find Deal
Fri, 1 May - Wed, 13 May
Delta Logo
14:15 - 22:22SYD-MDW
25h 07m2 stops
Delta Logo
13:26 - 08:30MDW-SYD
26h 04m2 stops
$2,194Delta
Find Deal
Thu, 25 Dec - Thu, 22 Jan
Delta Logo
10:40 - 17:45SYD-MDW
24h 05m2 stops
Delta Logo
13:09 - 07:30MDW-SYD
26h 21m2 stops
$2,215Delta
Find Deal
Fri, 27 Feb - Fri, 13 Mar
Delta Logo
10:40 - 17:45SYD-MDW
24h 05m2 stops
Delta Logo
13:09 - 07:30MDW-SYD
26h 21m2 stops
$2,218Delta
Find Deal
Fri, 27 Feb - Fri, 13 Mar
Delta Logo
10:40 - 22:07SYD-MDW
28h 27m2 stops
Delta Logo
10:48 - 08:30MDW-SYD
28h 42m2 stops
$2,311Delta
Find Deal
Sat, 17 Jan - Fri, 23 Jan
Delta Logo
14:15 - 22:22SYD-MDW
25h 07m2 stops
Delta Logo
13:28 - 06:50MDW-SYD
24h 22m2 stops
$2,375Delta
Find Deal
Thu, 25 Dec - Sat, 10 Jan
Multiple Airlines Logo
17:45 - 21:58SYD-MDW
45h 13m2 stops
Multiple Airlines Logo
06:10 - 07:25MDW-SYD
32h 15m2 stops
$2,465Multiple Airlines
Find Deal
Tue, 23 Dec - Sat, 17 Jan
Delta Logo
10:25 - 18:40SYD-MDW
24h 15m2 stops
Delta Logo
13:05 - 06:35MDW-SYD
26h 30m2 stops
$2,517Delta
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Fri, 3 Apr - Wed, 29 Apr

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
4 Dec
SYD10:40Sydney Kingsford Smith
30h 07m
2 stops
MDW23:47Chicago Midway
8 Dec
MDW17:29Chicago Midway
46h 01m
2 stops
SYD08:30Sydney Kingsford Smith
$1,806
Find similar
Delta
4 Dec
SYD10:40Sydney Kingsford Smith
30h 07m
2 stops
MDW23:47Chicago Midway
8 Dec
MDW18:40Chicago Midway
44h 50m
2 stops
SYD08:30Sydney Kingsford Smith
$1,808
Find similar
Delta
4 Dec
SYD10:40Sydney Kingsford Smith
30h 07m
2 stops
MDW23:47Chicago Midway
8 Dec
MDW17:29Chicago Midway
46h 01m
2 stops
SYD08:30Sydney Kingsford Smith
$1,812
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 30 November 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 29/4

09:25-21:45

2 stops27h 20m

Chicago Midway

Mon 11/5

14:00-06:35

2 stops25h 35m

$2,065

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 12/1

10:40-17:34

2 stops23h 54m

Chicago Midway

Mon 19/1

09:50-08:30

2 stops29h 40m

$2,085

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/5

09:25-18:05

2 stops23h 40m

Chicago Midway

Wed 13/5

14:00-06:35

2 stops25h 35m

$2,140

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Thu 22/1

13:26-08:30

2 stops26h 04m

$2,194

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 27/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Fri 13/3

13:09-07:30

2 stops26h 21m

$2,215

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 27/2

10:40-17:45

2 stops24h 05m

Chicago Midway

Fri 13/3

13:09-07:30

2 stops26h 21m

$2,218

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 17/1

10:40-22:07

2 stops28h 27m

Chicago Midway

Fri 23/1

10:48-08:30

2 stops28h 42m

$2,311

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 25/12

14:15-22:22

2 stops25h 07m

Chicago Midway

Sat 10/1

13:28-06:50

2 stops24h 22m

$2,375

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 23/12

17:45-21:58

2 stops45h 13m

Chicago Midway

Sat 17/1

06:10-07:25

2 stops32h 15m

$2,465

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 3/4

10:25-18:40

2 stops24h 15m

Chicago Midway

Wed 29/4

13:05-06:35

2 stops26h 30m

$2,517

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 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 40m

Direct flights

None
The fastest flight from Sydney to Chicago Midway Airport takes 23h 40m
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 22h 54m, 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.

An easier way to manage your Chicago Midway Airport trip

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