Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Sydney to Chicago from $873

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.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 - 4:53 pm
SYD
-
MDW
23h 13m2 stops
Delta Logo
1:09 pm - 6:35 am
MDW
-
SYD
26h 26m2 stops
$1,370Delta
Wed, Mar 25 - Mon, Apr 6
Delta Logo
9:15 am - 9:45 pm
SYD
-
MDW
27h 30m2 stops
Delta Logo
1:05 pm - 6:35 am
MDW
-
SYD
26h 30m2 stops
$1,494Delta
Fri, Jun 12 - Sun, Jul 12
Delta Logo
2:15 pm - 10:22 pm
SYD
-
MDW
25h 07m2 stops
Delta Logo
1:51 pm - 8:30 am
MDW
-
SYD
25h 39m2 stops
$1,568Delta
Mon, Feb 2 - Mon, Feb 9
Delta Logo
9:15 am - 6:31 pm
SYD
-
MDW
24h 16m2 stops
Delta Logo
1:05 pm - 6:35 am
MDW
-
SYD
26h 30m2 stops
$1,569Delta
Fri, Jun 12 - Sun, Jul 12
Delta Logo
2:15 pm - 10:22 pm
SYD
-
MDW
25h 07m2 stops
Delta Logo
1:29 pm - 6:50 am
MDW
-
SYD
24h 21m2 stops
$1,717Delta
Mon, Feb 9 - Thu, Feb 12
Multiple Airlines Logo
2:05 pm - 1:09 pm
SYD
-
MDW
40h 04m1 stop
Multiple Airlines Logo
8:15 am - 6:55 am
MDW
-
SYD
53h 40m2 stops
$4,238Multiple Airlines
Fri, Jan 2 - Mon, Jan 5
Multiple Airlines Logo
8:30 pm - 3:20 pm
SYD
-
MDW
35h 50m3 stops
Multiple Airlines Logo
11:05 am - 9:35 am
MDW
-
SYD
29h 30m3 stops
$4,859Multiple Airlines
Fri, Jan 2 - Mon, Jan 5
Delta Logo
10:40 am - 10:22 pm
SYD
-
MDW
28h 42m2 stops
Delta Logo
1:49 pm - 8:30 am
MDW
-
SYD
25h 41m2 stops
$5,411Delta
Fri, Jan 2 - Mon, Jan 5
Multiple Airlines Logo
9:10 am - 10:31 pm
SYD
-
MDW
30h 21m2 stops
Multiple Airlines Logo
9:35 am - 6:55 am
MDW
-
SYD
29h 20m2 stops
$11,622Multiple Airlines
Thu, Feb 12 - Thu, Mar 12
Korean Air Logo
9:10 am - 10:22 pm
SYD
-
MDW
30h 12m2 stops
Korean Air Logo
6:00 am - 6:55 am
MDW
-
SYD
31h 55m2 stops
$12,575Korean Air
Tue, Feb 10 - Tue, Feb 24

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
Dec 25
SYD10:40 amSydney Kingsford Smith
28h 42m
2 stops
MDW10:22 pmChicago Midway
Jan 21
MDW1:49 pmChicago Midway
25h 41m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,144
Find similar
Delta
Dec 25
SYD10:40 amSydney Kingsford Smith
23h 39m
2 stops
MDW5:19 pmChicago Midway
Jan 21
MDW9:50 amChicago Midway
29h 40m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,331
Find similar
Delta
Mar 25
SYD9:40 amSydney Kingsford Smith
23h 13m
2 stops
MDW4:53 pmChicago Midway
Apr 6
MDW1:09 pmChicago Midway
26h 26m
2 stops
SYD6:35 amSydney Kingsford Smith
$1,370
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 December 21, 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 3/25

9:40 am-4:53 pm

2 stops23h 13m

Chicago Midway

Mon 4/6

1:09 pm-6:35 am

2 stops26h 26m

$1,370

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/12

9:15 am-9:45 pm

2 stops27h 30m

Chicago Midway

Sun 7/12

1:05 pm-6:35 am

2 stops26h 30m

$1,494

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/2

2:15 pm-10:22 pm

2 stops25h 07m

Chicago Midway

Mon 2/9

1:51 pm-8:30 am

2 stops25h 39m

$1,568

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 6/12

9:15 am-6:31 pm

2 stops24h 16m

Chicago Midway

Sun 7/12

1:05 pm-6:35 am

2 stops26h 30m

$1,569

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Mon 2/9

2:15 pm-10:22 pm

2 stops25h 07m

Chicago Midway

Thu 2/12

1:29 pm-6:50 am

2 stops24h 21m

$1,717

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/2

2:05 pm-1:09 pm

1 stop40h 04m

Chicago Midway

Mon 1/5

8:15 am-6:55 am

2 stops53h 40m

$4,238

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/2

8:30 pm-3:20 pm

3 stops35h 50m

Chicago Midway

Mon 1/5

11:05 am-9:35 am

3 stops29h 30m

$4,859

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 1/2

10:40 am-10:22 pm

2 stops28h 42m

Chicago Midway

Mon 1/5

1:49 pm-8:30 am

2 stops25h 41m

$5,411

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Thu 2/12

9:10 am-10:31 pm

2 stops30h 21m

Chicago Midway

Thu 3/12

9:35 am-6:55 am

2 stops29h 20m

$11,622

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 2/10

9:10 am-10:22 pm

2 stops30h 12m

Chicago Midway

Tue 2/24

6:00 am-6:55 am

2 stops31h 55m

$12,575

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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

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?

    Chicago Midway is 9230.4 mi away from Sydney Kingsford Smith. A reasonable flight in good conditions will take 23h 13m.

  • 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
Valparaiso
Schererville
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Tue 1/20
Tue 1/27
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago