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Cheap flights from Sydney to Chicago from $686

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 4/15. 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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Find the cheapest flights from Sydney to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:40 am - 5:54 pm
SYD
-
MDW
24h 14m
2 stops
Delta Logo
12:53 pm - 6:50 am
MDW
-
SYD
26h 57m
2 stops
$1,199Delta
Thu, Mar 19 - Tue, Apr 21
Delta Logo
9:40 am - 6:40 pm
SYD
-
MDW
25h 00m
2 stops
Delta Logo
1:23 pm - 6:50 am
MDW
-
SYD
26h 27m
2 stops
$1,202Delta
Thu, Mar 19 - Tue, Apr 21
Multiple Airlines Logo
1:05 pm - 8:21 pm
SYD
-
MDW
23h 16m
1 stop
Multiple Airlines Logo
9:16 pm - 6:55 am
MDW
-
SYD
41h 39m
1 stop
$1,381Multiple Airlines
Sat, Mar 21 - Sat, Mar 28
Delta Logo
9:40 am - 5:54 pm
SYD
-
MDW
24h 14m
2 stops
Delta Logo
10:45 am - 6:50 am
MDW
-
SYD
29h 05m
2 stops
$1,489Delta
Fri, Mar 27 - Mon, Apr 6
Delta Logo
9:15 am - 6:36 pm
SYD
-
MDW
24h 21m
2 stops
Delta Logo
1:59 pm - 6:50 am
MDW
-
SYD
25h 51m
2 stops
$1,492Delta
Fri, Apr 24 - Sun, May 10
Delta Logo
9:15 am - 6:36 pm
SYD
-
MDW
24h 21m
2 stops
Delta Logo
1:22 pm - 6:50 am
MDW
-
SYD
26h 28m
2 stops
$1,544Delta
Sat, Apr 25 - Sat, May 9
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
Delta Logo
1:00 pm - 6:50 am
MDW
-
SYD
26h 50m
2 stops
$1,625Delta
Wed, Jul 8 - Wed, Jul 15
Delta Logo
10:40 am - 5:37 pm
SYD
-
MDW
23h 57m
2 stops
Delta Logo
1:10 pm - 7:25 am
MDW
-
SYD
26h 15m
2 stops
$1,649Delta
Mon, Mar 2 - Mon, Mar 9
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
Delta Logo
2:00 pm - 6:50 am
MDW
-
SYD
25h 50m
2 stops
$1,677Delta
Fri, Jul 10 - Sun, Jul 26
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m
2 stops
Delta Logo
2:00 pm - 6:50 am
MDW
-
SYD
25h 50m
2 stops
$1,678Delta
Fri, Jul 10 - Sun, Jul 26

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
Mar 19
SYD9:40 amSydney Kingsford Smith
24h 14m
2 stops
MDW5:54 pmChicago Midway
Apr 21
MDW12:53 pmChicago Midway
26h 57m
2 stops
SYD6:50 amSydney Kingsford Smith
$1,199
Delta
Mar 19
SYD9:40 amSydney Kingsford Smith
25h 00m
2 stops
MDW6:40 pmChicago Midway
Apr 21
MDW1:23 pmChicago Midway
26h 27m
2 stops
SYD6:50 amSydney Kingsford Smith
$1,202
Delta
Mar 19
SYD9:40 amSydney Kingsford Smith
25h 00m
2 stops
MDW6:40 pmChicago Midway
Apr 21
MDW2:12 pmChicago Midway
25h 38m
2 stops
SYD6:50 amSydney Kingsford Smith
$1,209

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 February 4, 2026.
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 3/19

9:40 am-5:54 pm

2 stops24h 14m

Chicago Midway

Tue 4/21

12:53 pm-6:50 am

2 stops26h 57m

$1,199

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 3/19

9:40 am-6:40 pm

2 stops25h 00m

Chicago Midway

Tue 4/21

1:23 pm-6:50 am

2 stops26h 27m

$1,202

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 3/21

1:05 pm-8:21 pm

1 stop23h 16m

Chicago Midway

Sat 3/28

9:16 pm-6:55 am

1 stop41h 39m

$1,381

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 3/27

9:40 am-5:54 pm

2 stops24h 14m

Chicago Midway

Mon 4/6

10:45 am-6:50 am

2 stops29h 05m

$1,489

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 4/24

9:15 am-6:36 pm

2 stops24h 21m

Chicago Midway

Sun 5/10

1:59 pm-6:50 am

2 stops25h 51m

$1,492

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 4/25

9:15 am-6:36 pm

2 stops24h 21m

Chicago Midway

Sat 5/9

1:22 pm-6:50 am

2 stops26h 28m

$1,544

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 7/8

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Wed 7/15

1:00 pm-6:50 am

2 stops26h 50m

$1,625

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 3/2

10:40 am-5:37 pm

2 stops23h 57m

Chicago Midway

Mon 3/9

1:10 pm-7:25 am

2 stops26h 15m

$1,649

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 7/10

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Sun 7/26

2:00 pm-6:50 am

2 stops25h 50m

$1,677

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 7/10

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Sun 7/26

2:00 pm-6:50 am

2 stops25h 50m

$1,678

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

Fastest flight time

24h 05m

Direct flights

None
The fastest flight from Sydney to Chicago Midway Airport takes 24h 05m
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?

    Chicago Midway is 9230.4 mi away from Sydney Kingsford Smith. A reasonable flight in good conditions will take 24h 05m.

  • 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
Munster
Crown Point
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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