Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Sydney to Chicago from $490

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 10/15. 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

Multiple Airlines Logo
11:20 am - 12:37 pmSYD-MDW
41h 17m2 stops
Multiple Airlines Logo
6:30 am - 9:00 amMDW-SYD
33h 30m2 stops
$1,014Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Multiple Airlines Logo
11:20 am - 12:30 pmSYD-MDW
41h 10m2 stops
Multiple Airlines Logo
6:15 am - 9:00 amMDW-SYD
33h 45m2 stops
$1,074Multiple Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 15
Multiple Airlines Logo
11:20 am - 12:37 pmSYD-MDW
41h 17m2 stops
Multiple Airlines Logo
6:30 am - 9:00 amMDW-SYD
33h 30m2 stops
$1,099Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Delta Logo
10:40 am - 4:38 pmSYD-MDW
22h 58m2 stops
Delta Logo
12:47 pm - 8:30 amMDW-SYD
26h 43m2 stops
$1,382Delta
Find Deal
Tue, Nov 18 - Tue, Nov 25
Delta Logo
10:40 am - 6:25 pmSYD-MDW
24h 45m2 stops
Delta Logo
9:41 am - 8:30 amMDW-SYD
29h 49m2 stops
$1,480Delta
Find Deal
Sat, Nov 8 - Sat, Nov 22
Delta Logo
9:25 am - 5:35 pmSYD-MDW
23h 10m2 stops
Delta Logo
12:47 pm - 8:30 amMDW-SYD
26h 43m2 stops
$1,680Delta
Find Deal
Tue, Sep 30 - Wed, Nov 12
Delta Logo
9:25 am - 6:35 pmSYD-MDW
24h 10m2 stops
Delta Logo
10:47 am - 8:30 amMDW-SYD
28h 43m2 stops
$1,682Delta
Find Deal
Tue, Sep 30 - Wed, Nov 12
Multiple Airlines Logo
1:05 pm - 5:15 pmSYD-MDW
20h 10m1 stop
Multiple Airlines Logo
6:30 am - 7:25 amMDW-SYD
31h 55m2 stops
$1,801Multiple Airlines
Find Deal
Fri, Oct 31 - Fri, Nov 7
Korean Air Logo
7:55 am - 12:28 pmSYD-MDW
43h 33m2 stops
Korean Air Logo
6:00 am - 6:55 amMDW-SYD
31h 55m2 stops
$5,691Korean Air
Find Deal
Wed, Oct 1 - Wed, Feb 11
Korean Air Logo
9:10 am - 10:16 pmSYD-MDW
30h 06m2 stops
Korean Air Logo
6:00 am - 6:55 amMDW-SYD
31h 55m2 stops
$5,899Korean Air
Find Deal
Sat, Dec 20 - Tue, Dec 30

Delta flights from Sydney to Chicago Midway Airport

Our best Delta deals on Sydney to Chicago Midway Airport flight tickets
Delta
Nov 18
SYD10:40 amSydney Kingsford Smith
22h 58m
2 stops
MDW4:38 pmChicago Midway
Nov 25
MDW12:47 pmChicago Midway
26h 43m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,382
Find similar
Delta
Nov 8
SYD10:40 amSydney Kingsford Smith
24h 45m
2 stops
MDW6:25 pmChicago Midway
Nov 22
MDW9:41 amChicago Midway
29h 49m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,480
Find similar
Delta
Sep 30
SYD9:25 amSydney Kingsford Smith
23h 10m
2 stops
MDW5:35 pmChicago Midway
Nov 12
MDW12:47 pmChicago Midway
26h 43m
2 stops
SYD8:30 amSydney Kingsford Smith
$1,680
Find similar

Korean Air flights from Sydney to Chicago Midway Airport

Our best Korean Air deals on Sydney to Chicago Midway Airport flight tickets
Korean Air
Oct 1
SYD7:55 amSydney Kingsford Smith
43h 33m
2 stops
MDW12:28 pmChicago Midway
Feb 11
MDW6:00 amChicago Midway
31h 55m
2 stops
SYD6:55 amSydney Kingsford Smith
$5,691
Find similar
Korean Air
Dec 20
SYD9:10 amSydney Kingsford Smith
30h 06m
2 stops
MDW10:16 pmChicago Midway
Dec 30
MDW6:00 amChicago Midway
31h 55m
2 stops
SYD6:55 amSydney Kingsford Smith
$5,899
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 September 18, 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

Fri 10/31

11:20 am-12:37 pm

2 stops41h 17m

Chicago Midway

Fri 11/7

6:30 am-9:00 am

2 stops33h 30m

$1,014

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 11/1

11:20 am-12:30 pm

2 stops41h 10m

Chicago Midway

Sat 11/15

6:15 am-9:00 am

2 stops33h 45m

$1,074

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/31

11:20 am-12:37 pm

2 stops41h 17m

Chicago Midway

Fri 11/7

6:30 am-9:00 am

2 stops33h 30m

$1,099

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 11/18

10:40 am-4:38 pm

2 stops22h 58m

Chicago Midway

Tue 11/25

12:47 pm-8:30 am

2 stops26h 43m

$1,382

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 11/8

10:40 am-6:25 pm

2 stops24h 45m

Chicago Midway

Sat 11/22

9:41 am-8:30 am

2 stops29h 49m

$1,480

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 9/30

9:25 am-5:35 pm

2 stops23h 10m

Chicago Midway

Wed 11/12

12:47 pm-8:30 am

2 stops26h 43m

$1,680

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Tue 9/30

9:25 am-6:35 pm

2 stops24h 10m

Chicago Midway

Wed 11/12

10:47 am-8:30 am

2 stops28h 43m

$1,682

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Fri 10/31

1:05 pm-5:15 pm

1 stop20h 10m

Chicago Midway

Fri 11/7

6:30 am-7:25 am

2 stops31h 55m

$1,801

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Wed 10/1

7:55 am-12:28 pm

2 stops43h 33m

Chicago Midway

Wed 2/11

6:00 am-6:55 am

2 stops31h 55m

$5,691

SydneyChicago

SYD - MDW

SYDMDW

Sydney Kingsford Smith

Sat 12/20

9:10 am-10:16 pm

2 stops30h 06m

Chicago Midway

Tue 12/30

6:00 am-6:55 am

2 stops31h 55m

$5,899

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 and Korean Air 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

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.
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 20h 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
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
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.

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
Sat 10/18
Sat 10/25
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago