Cheap flights from Sydney to Chicago from $728

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 11/15. 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 round-trip flights

Delta Logo
10:40 am - 6:34 pmSYD-MDW
24h 54m2 stops
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
$1,350Delta
Find Deal
Mon, Jan 12 - Sun, Feb 1
Delta Logo
9:40 am - 6:25 pmSYD-MDW
24h 45m2 stops
Delta Logo
1:00 pm - 8:30 amMDW-SYD
26h 30m2 stops
$1,392Delta
Find Deal
Wed, Oct 29 - Sat, Nov 15
Delta Logo
9:25 am - 9:26 pmSYD-MDW
27h 01m2 stops
Delta Logo
1:08 pm - 7:35 amMDW-SYD
26h 27m2 stops
$1,546Delta
Find Deal
Mon, Sep 8 - Sun, Oct 5
Delta Logo
9:25 am - 8:50 amSYD-MDW
38h 25m2 stops
Delta Logo
9:20 am - 7:35 amMDW-SYD
30h 15m2 stops
$1,563Delta
Find Deal
Tue, Aug 26 - Mon, Oct 20
Delta Logo
9:25 am - 9:26 pmSYD-MDW
27h 01m2 stops
Delta Logo
9:20 am - 7:35 amMDW-SYD
30h 15m2 stops
$1,595Delta
Find Deal
Wed, Sep 10 - Wed, Oct 8
Delta Logo
10:25 am - 1:08 pmSYD-MDW
42h 43m2 stops
Delta Logo
1:08 pm - 7:30 amMDW-SYD
26h 22m2 stops
$1,635Delta
Find Deal
Thu, Oct 23 - Mon, Oct 27
Delta Logo
9:25 am - 5:47 pmSYD-MDW
23h 22m2 stops
Delta Logo
10:31 am - 6:35 amMDW-SYD
29h 04m2 stops
$1,644Delta
Find Deal
Mon, Aug 11 - Wed, Sep 3
Delta Logo
9:25 am - 5:35 pmSYD-MDW
23h 10m2 stops
Delta Logo
12:43 pm - 6:35 amMDW-SYD
26h 52m2 stops
$1,650Delta
Find Deal
Fri, Sep 12 - Fri, Sep 19
 Logo
6:20 pm - 2:37 pmSYD-MDW
59h 17m2 stops
 Logo
6:15 pm - 6:55 amMDW-SYD
44h 40m1 stop
$2,473
Find Deal
Tue, Aug 26 - Mon, Oct 20
 Logo
7:55 am - 12:28 pmSYD-MDW
43h 33m2 stops
 Logo
9:15 am - 6:20 amMDW-SYD
30h 05m2 stops
$11,048
Find Deal
Sun, Aug 24 - Thu, Sep 4

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
Jan 12
SYD10:40 amSydney Kingsford Smith
24h 54m
2 stops
MDW6:34 pmChicago Midway
Feb 1
MDW1:00 pmChicago Midway
26h 30m
2 stops
SYD8:30 amSydney Kingsford Smith
Delta
Oct 29
SYD9:40 amSydney Kingsford Smith
24h 45m
2 stops
MDW6:25 pmChicago Midway
Nov 15
MDW1:00 pmChicago Midway
26h 30m
2 stops
SYD8:30 amSydney Kingsford Smith
Delta
Sep 8
SYD9:25 amSydney Kingsford Smith
27h 01m
2 stops
MDW9:26 pmChicago Midway
Oct 5
MDW1:08 pmChicago Midway
26h 27m
2 stops
SYD7:35 amSydney Kingsford Smith

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated July 31, 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

Mon 1/12

10:40 am-6:34 pm

2 stops24h 54m

Chicago Midway

Sun 2/1

1:00 pm-8:30 am

2 stops26h 30m

$1,350

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/29

9:40 am-6:25 pm

2 stops24h 45m

Chicago Midway

Sat 11/15

1:00 pm-8:30 am

2 stops26h 30m

$1,392

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 9/8

9:25 am-9:26 pm

2 stops27h 01m

Chicago Midway

Sun 10/5

1:08 pm-7:35 am

2 stops26h 27m

$1,546

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 8/26

9:25 am-8:50 am

2 stops38h 25m

Chicago Midway

Mon 10/20

9:20 am-7:35 am

2 stops30h 15m

$1,563

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 9/10

9:25 am-9:26 pm

2 stops27h 01m

Chicago Midway

Wed 10/8

9:20 am-7:35 am

2 stops30h 15m

$1,595

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 10/23

10:25 am-1:08 pm

2 stops42h 43m

Chicago Midway

Mon 10/27

1:08 pm-7:30 am

2 stops26h 22m

$1,635

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 8/11

9:25 am-5:47 pm

2 stops23h 22m

Chicago Midway

Wed 9/3

10:31 am-6:35 am

2 stops29h 04m

$1,644

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 9/12

9:25 am-5:35 pm

2 stops23h 10m

Chicago Midway

Fri 9/19

12:43 pm-6:35 am

2 stops26h 52m

$1,650

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 8/26

6:20 pm-2:37 pm

2 stops59h 17m

Chicago Midway

Mon 10/20

6:15 pm-6:55 am

1 stop44h 40m

$2,473

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 8/24

7:55 am-12:28 pm

2 stops43h 33m

Chicago Midway

Thu 9/4

9:15 am-6:20 am

2 stops30h 05m

$11,048

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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, Korean Air, and WestJet are the most popular carriers 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 round-trip 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

$728

Fastest flight time

20h 00m

Direct flights

None
The best one-way flight to Chicago Midway Airport from Sydney in the past 72 hours is $728. The best round-trip flight deal from Sydney to Chicago Midway Airport found on momondo in the last 72 hours is $1,350.
The fastest flight from Sydney to Chicago Midway Airport takes 20h 00m
There are no direct flights from Sydney to Chicago Midway Airport. Popular non-direct route for this connection is Sydney Kingsford Smith Airport - Chicago Midway Airport.

  • How far is Sydney Kingsford Smith to Chicago Midway by plane?

    Chicago Midway is 9230.4 mi away from Sydney Kingsford Smith. A reasonable flight in good conditions will take 23h 10m.

  • 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 were last updated today.

  • How old do you have to be to fly from Sydney Kingsford Smith Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to 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 license, 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.


Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Sydney to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sydney to Chicago for you.

Can I find flights from Sydney to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Sydney to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Sydney to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Sydney to Chicago.

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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