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Cheap flights from Sydney to Chicago from $772

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 11/19. 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

Enter your travel dates to find the best prices.
Delta Logo
10:40 am - 6:18 pmSYD-MDW
24h 38m2 stops
Delta Logo
1:15 pm - 8:30 amMDW-SYD
26h 15m2 stops
$989Delta
Find Deal
Thu, Nov 13 - Wed, Nov 26
Multiple Airlines Logo
11:20 am - 8:46 amSYD-MDW
38h 26m2 stops
Multiple Airlines Logo
6:12 am - 9:00 amMDW-SYD
33h 48m2 stops
$1,001Multiple Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 31
Multiple Airlines Logo
5:45 pm - 9:52 amSYD-MDW
33h 07m2 stops
Multiple Airlines Logo
6:12 am - 9:00 amMDW-SYD
33h 48m2 stops
$1,057Multiple Airlines
Find Deal
Sun, Dec 7 - Wed, Dec 31
Delta Logo
10:40 am - 11:40 pmSYD-MDW
30h 00m2 stops
Delta Logo
1:47 pm - 8:30 amMDW-SYD
25h 43m2 stops
$1,136Delta
Find Deal
Sun, Nov 16 - Sun, Nov 30
Delta Logo
10:40 am - 11:40 pmSYD-MDW
30h 00m2 stops
Delta Logo
9:41 am - 8:30 amMDW-SYD
29h 49m2 stops
$1,137Delta
Find Deal
Sun, Nov 23 - Sun, Nov 30
Delta Logo
10:40 am - 5:19 pmSYD-MDW
23h 39m2 stops
Delta Logo
1:49 pm - 8:30 amMDW-SYD
25h 41m2 stops
$1,419Delta
Find Deal
Thu, Dec 25 - Thu, Jan 22
Delta Logo
10:40 am - 11:47 pmSYD-MDW
30h 07m2 stops
Delta Logo
1:28 pm - 8:30 amMDW-SYD
26h 02m2 stops
$1,517Delta
Find Deal
Wed, Dec 10 - Thu, Jan 15
Delta Logo
10:40 am - 5:19 pmSYD-MDW
23h 39m2 stops
Delta Logo
11:45 am - 8:30 amMDW-SYD
27h 45m2 stops
$1,677Delta
Find Deal
Sun, Dec 21 - Sat, Jan 10
Delta Logo
10:40 am - 11:47 pmSYD-MDW
30h 07m2 stops
Delta Logo
11:48 am - 8:30 amMDW-SYD
27h 42m2 stops
$2,330Delta
Find Deal
Sun, Dec 14 - Fri, Jan 2
Delta Logo
10:40 am - 11:47 pmSYD-MDW
30h 07m2 stops
Delta Logo
9:50 am - 8:30 amMDW-SYD
29h 40m2 stops
$2,379Delta
Find Deal
Sun, Dec 14 - Fri, Jan 2

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
Nov 13
SYD10:40 amSydney Kingsford Smith
24h 38m
2 stops
MDW6:18 pmChicago Midway
Nov 26
MDW1:15 pmChicago Midway
26h 15m
2 stops
SYD8:30 amSydney Kingsford Smith
$989
Find similar
Delta
Nov 16
SYD10:40 amSydney Kingsford Smith
30h 00m
2 stops
MDW11:40 pmChicago Midway
Nov 30
MDW1:47 pmChicago Midway
25h 43m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,136
Find similar
Delta
Nov 23
SYD10:40 amSydney Kingsford Smith
30h 00m
2 stops
MDW11:40 pmChicago Midway
Nov 30
MDW9:41 amChicago Midway
29h 49m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,137
Find similar

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 November 3, 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

Thu 11/13

10:40 am-6:18 pm

2 stops24h 38m

Chicago Midway

Wed 11/26

1:15 pm-8:30 am

2 stops26h 15m

$989

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 12/8

11:20 am-8:46 am

2 stops38h 26m

Chicago Midway

Wed 12/31

6:12 am-9:00 am

2 stops33h 48m

$1,001

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/7

5:45 pm-9:52 am

2 stops33h 07m

Chicago Midway

Wed 12/31

6:12 am-9:00 am

2 stops33h 48m

$1,057

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 11/16

10:40 am-11:40 pm

2 stops30h 00m

Chicago Midway

Sun 11/30

1:47 pm-8:30 am

2 stops25h 43m

$1,136

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 11/23

10:40 am-11:40 pm

2 stops30h 00m

Chicago Midway

Sun 11/30

9:41 am-8:30 am

2 stops29h 49m

$1,137

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 12/25

10:40 am-5:19 pm

2 stops23h 39m

Chicago Midway

Thu 1/22

1:49 pm-8:30 am

2 stops25h 41m

$1,419

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 12/10

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Thu 1/15

1:28 pm-8:30 am

2 stops26h 02m

$1,517

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/21

10:40 am-5:19 pm

2 stops23h 39m

Chicago Midway

Sat 1/10

11:45 am-8:30 am

2 stops27h 45m

$1,677

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/14

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Fri 1/2

11:48 am-8:30 am

2 stops27h 42m

$2,330

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sun 12/14

10:40 am-11:47 pm

2 stops30h 07m

Chicago Midway

Fri 1/2

9:50 am-8:30 am

2 stops29h 40m

$2,379

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 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 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

Direct flights

None
There are no direct flights from Sydney to Chicago Midway Airport. There are no popular flight routes from Sydney to Chicago Midway Airport.
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  • 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 39m.

  • 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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